硝基吡唑及其衍生物的合成、性能及应用研究进展
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摘要
硝基吡唑及其衍生物具有高生成热,良好的热稳定性和爆轰性能,在含能材料领域具有广阔的应用前景。从硝基吡唑及其衍生物的合成、性能及应用等角度对其近年来的研究进展进行了简要综述,梳理了硝基吡唑及其衍生物合成研究的发展方向和趋势,指出了今后研究的重点方向:认为必须探索、寻找新的合成路线并优化其工艺条件,缩短反应步骤、提高反应效率,实现硝基吡唑化合物高品质化、规模化、稳定化制备,进一步探索绿色环保、可循环使用的高效重排试剂、萃取剂及重结晶介质,加强1?甲基?3,4,5?三硝基吡唑(MTNP)与3,4?二硝基吡唑(3,4?DNP)的基础性能综合研究,开展其熔融?凝固后的体积收缩特性及安全性能研究,综合评估其在熔铸炸药中的应用可行性,拓展其在高能钝感炸药中的应用。
Nitropyrazole and its derivatives have high heat of formation,good thermal stability and detonation performances,which have broad application prospects in the field of energetic materials. Their research progress in recent years is briefly re?viewed from the aspects of synthesis,properties and applications of nitropyrazole and its derivatives,and the development direc?tion and trend of the research on the synthesis of nitropyrazole and its derivatives are combed. Several important directions in the future research are pointed out:considering that ones have need to explore and find new synthetic routes and optimize their technological conditions,shorten reaction steps,improve reaction efficiency,and realize high?quality,large?scale and stabiliza?tion preparation of nitropyrazole compounds,and to further explore the green environmental protection and recyclable high?effi?ciency rearrangement reagents,extraction agents and recrystallization media,strengthen the comprehensive research on the ba?sic properties of MTNP and 3,4?DNP,carry out the research on their volume shrinkage characteristics and safety properties after melting and solidification,comprehensively evaluate the feasibility of their application in fused cast explosives,and further ex?pand their application research in high energy insensitive explosives.
Nitropyrazole and its derivatives have high heat of formation,good thermal stability and detonation performances,which have broad application prospects in the field of energetic materials. Their research progress in recent years is briefly re?viewed from the aspects of synthesis,properties and applications of nitropyrazole and its derivatives,and the development direc?tion and trend of the research on the synthesis of nitropyrazole and its derivatives are combed. Several important directions in the future research are pointed out:considering that ones have need to explore and find new synthetic routes and optimize their technological conditions,shorten reaction steps,improve reaction efficiency,and realize high?quality,large?scale and stabiliza?tion preparation of nitropyrazole compounds,and to further explore the green environmental protection and recyclable high?effi?ciency rearrangement reagents,extraction agents and recrystallization media,strengthen the comprehensive research on the ba?sic properties of MTNP and 3,4?DNP,carry out the research on their volume shrinkage characteristics and safety properties after melting and solidification,comprehensively evaluate the feasibility of their application in fused cast explosives,and further ex?pand their application research in high energy insensitive explosives.
引文
[1]汪营磊,姬月萍,陈斌,等.3,4?二硝基吡唑合成与性能研究[J].含能材料,2011,19(4):377-379.WANG Ying?lei,JI Yue?ping,CHEN Bin,et al. Improved syn?thesis of 3,4?dinitropyrazole[J]. Chinese Journal of Energetic Materials(Hanneng Cailiao),2011,19(4):377-379.
[2]杨克明,曹端林,李永祥,等.1?甲基?3,5?二硝基?1,2,4?三唑的合成及表征[J].含能材料,2011(6):501-504.YANG Ke?ming,CAO Duan?lin,LI Yong?xiang,et al. Synthesis and characterization of 1?methyl?3,5?dininitro?1,2,4?trazole[J].Chinese Journal of Energetic Materials(Hanneng Cailiao),2011(6):501-504.
[3]柴春鹏,甘志勇,李娜,等.3?硝基?1,2,4?三唑?5?酮银盐的合成和热分解性能[J].火炸药学报,2011,34(2):36-38.CHAI Chun?peng,GAN Zhi?yong,LI Na,et al. Synthesis and thermal decomposition behavior of 3?nitro?1,2,4?triazol?5?one silver salt[J]. Chinese Journal of Explosives&Propellants,2011,34(2):36-38.
[4]高红旭,赵凤起,胡荣祖,等.六硝基六氮杂异戊兹烷的热分解反应动力学参数和热安全性评估[J].火炸药学报,2013,36(5):41-48.GAO Hong?xu,ZHAO Feng?qi,HU Rong?zu,et al. Estimation of the kinetic parameters of thermal decomposition reaction and thermal safety on hexanitrohexaazaisowurtzitane[J]. Chinese Journal of Explosives&Propellants,2013,36(5):41-48.
[5]阳世清,徐松林,雷永鹏.氮杂环含能化合物的研究进展[J].含能材料,2006,14(6):475-484.YANG Shi?qing,XU Song?lin,LEI Yong?peng. The research progress of nitrogen heterocyclic compounds[J]. Chinese Journal of Energetic Materials(Hanneng Cailiao),2006,14(6):475-484.
[6] Agrawal J P,Hodgson R. Organic Chemistry of Explosives[M].John Wiley:New York,2007:294-296.
[7] Pagoria P F,Lee J S,Mitchell A R,et al.A review of energetic materials synthesis[J].ThermochimActa,2002,384:187.
[8] Larina L,Lopyrev L. Nitroazoles:Synthesis,Structure and Ap?plications[M].New York:Springer,2009.
[9]杨雨璋.多氮含能复合物的制备及其稳定性的研究[D].北京:北京理工大学,2016.YANG Yu?zhang.Study on the synthesis and stability of poly ni?trogen energetic compounds[D]. Beijing:Beijing Institute of Technology,2016.
[10]唐伟强,任慧,焦清介,等.3,4?二硝基吡唑的性能表征及应用[J].含能材料,2017,25(1):44-48.TANG Wei?qiang,REN Hui,JIAO Qing?jie,et al. Property char?acterization of 3,4?dinitropyrazole and its application[J].Chinese Journal of Energetic Materials(Hanneng Cailiao),2017,25(1):44-48.
[11] Dheeraj Kumar,Chunlin He,Lauren A. Mitchell,et al. Con?necting energetic nitropyrazole and aminotetrazole moieties with N,N′?ethylene bridges:A promising approach for fi ne tuning energetic properties[J].J Mater Chem A,2016,4(23):9220-9228.
[12] Nagarjuna Kommu,M Balaraju,Vikas D Ghule,et al.Synthetic manifestation of nitro substituted tetrazole?N?(hetero)aryl de?rivatives and energetic studies[J]. J. Mater. Chem. A,2017,5(16):7366-7371.
[13] Yongxing Tang,Dheeraj Kumar,Jean′ne M Shreeve. Balanc?ing excellent performance and high thermal stability in a dini?tropyrazole fused 1,2,3,4?tetrazine[J].J Am Chem Soc,2017,139(39):13684-13687.
[14] Depanjan Sarkar,Anirban Som,Thalappil Pradeep. Catalytic paper spray ionization mass spectrometry with metalnanotubes and the detection of 2,4,6?trinitrotoluene[J]. Anal Chem,2017,89(21):11378-11382.
[15]赵廷兴,李磊,董战,等.硝基唑类含能化合物的合成研究进展[J].有机化学,2013,34(2):304-315.ZHAO Ting?xing,LI Lei,DONG Zhan,et al. Research progress on the synthesis of energetic nitroazoles[J].Chinese Journal of Organic Chemistry,2013,34(2):304-315.
[16] Gao H,Shreeve J M. Azole?based energetic salts[J]. Chemical Reviews,2011,111(11):7377-7436.
[17]李翠屏,孙天旭,陈新志.3?硝基吡唑的合成[J].染料与染色,2004,41(3):168-169.LI Cui?ping,SUN Tian?xu,CHEN Xin?zhi. Synthesis of 3?nitro?pyrazole[J].Dyestuffsand Coloration,2004,41(3):168-169.
[18] Adrian Huang,Kellie Wo,So Yeun Christine Lee,et al. Regiose?lective synthesis, NMR, and crystallographic analysis of N1?substituted pyrazoles[J].J Org Chem,2017,82(17):8864-8872.
[19] Lahm G P,Cordova D,Barry J D. New and selective ryanodine receptor activators for insect control[J]. Bioorganic&Medicinal Chemistry,2009,17(12):4127-4133.
[20] Mowbray C E,Burt C,Corbau R,et al. Pyrazole NNRTIs 4:se?lection of UK?453,061(lersivirine)as adevelopment candidate[J]. Bioorganic and Medicinal Chemistry Letters,2009,19(20):5857-5860.
[21] Emma Cavero,Santiago Uriel,Pilar Romero,et al. Tetrahedral zinc complexes with liquid crystalline and luminescent proper?ties:interplay between nonconventional molecular shapes and supramolecular mesomorphic order[J]. JAmChemSoc,2007,129(37),11608-11618.
[22]王凤.5?氨基吡唑、1,2,4?吡唑膦衍生物及其CuⅡ、FeⅡ配合物的合成与结构研究[D].太原:山西师范大学,2014.WANG Feng. Synthesis and Structural Research of 5?Amino Pyrazole,1,2,4,?Diazaphospholes Derivatives and CuⅡ,FeⅡMetal Complese[D]:Taiyuan:Shanxi Normal University,2014.
[23] Janssen J W A M,Koeners H J. The preparation of 3(5)?nitre?pyrazoles by thermal rearran?gement of N?nitropyrazoles[J].J Org Chem,1973,38(10):1777-1782.
[24] Price D,Morris J. Synthesis of new energetic melt?pour candi?dates[C]//Insensitive Munitions and Energetic Materials Tech?nology Symposium,2009.
[25] Verbruggen R,Viehe H G. Cycloaddition with 2?chloro?1?nitro?ethelene[J].Chimia,1975,29(8):350-352.
[26]李洪丽,熊彬,姜俊,等.3?硝基吡唑及其盐类的合成与表征[J].火炸药学报,2007,31(2):102-108.LI Hong?li,XIONG Bin,JIANG Jun,et al. Synethsi and charac?terization of 3?nitropyrazole and its salts[J]. Chinese Journal of Explosives&Propellants,2007,31(2):102-108.
[27]田新,李金山,王军.3,4?二硝基吡唑的合成[J].合成化学,2012,20(1):117-122.TIAN Xin,LI Jin?shan,WANG Jun. Synthesis of 3,4?dinitropyr?azoles[J]. Chinese Journal of Synthetic Chemistry,2012,20(1):117-122.
[28] Hüttel R,Büchele F.Uber N?nitro?pyrazole[J].Chemische Berichte,1955,88(10):1586-1590.
[29] Kanishchev M I,Korneeva N V,Shevelev S A,et al. Nitropyr?azoles(Review)[M]. Plenum Publishing Corporation,1988:435-453.
[30] Rao E N,Ravi P,Tewari S P. Experimental and theoretical stud?ies on the structure and vibrational properties of nitropyrazoles[J].Journal of Molecular Structure,2013(1043):121-131.
[31] Ravi P. Experimental and DFT studies on the structure,infra?red and Raman spectral properties of dinitropyrazoles[J].Journal of Molecular Structure,2015,1079:433-447.
[32] Senomyx Inc,Karanewsky Donald S,Fotsing Joseph R,et al.Identification of human T2R receptors that respond to bitter compounds that elicit the bitter taste in compositions,and the use thereof in assays to identify compounds that inhibit(block)bitter taste in compositions and use thereof:US9247759[P],2016.
[33]李永祥,党鑫,曹端林,等.4?硝基吡唑的一锅两步法合成及其晶体结构[J].含能材料,2018,26(5):404 409.LI Yong?xiang,DANG Xin,CAO Duan?lin,et al. One?pot two steps synthesis of 4?nitropyrazole and its crystal structure[J].Chinese Joumal of Energetic Materials(Hanneng Cailiao),2018,26(5):404-409.
[34]郭俊玲,曹端林,王建龙,等.硝基吡唑类化合物的合成研究进展[J].含能材料,2014,22(6):872-879.GUO Jun?ling,CAO Duan?lin,WANG Jian?long,et al. Review on synthesis of nitropyrazoles[J]. Chinese Journal of Energetic Materials(Hanneng Cailiao),2014,22(6):872-879.
[35] Katritzky A R,Scriven E F V,Majumder S,et al. Direct nitration of five membered heterocycles[J]. Arkivoc(ⅲ),2005,36(10):179-191.
[36] Ravi P,Gore G M,Tewari S P,et al. A simple and environmen?tally benign nitration of pyrazoles by impregn nitration of pyr?azoles by impregnated bismuth nitrate[J].Journal of HeterocyclicChemistry,2013,50(6):1322-1327.
[37] J DONG,B ZHONG,H YUAN,et al.Alk kinase inhibitor,and preparation method and use thereof:WO 201580685 A1[P],2017.
[38]郭恒杰,曹端林,李永祥.1?甲基?3,4,5?三硝基吡唑合成工艺研究进展[J].云南化工,2018,45(5):88-90.GUO Heng?jie,CAO Duan?lin,LI Yong?xiang. Prospect on studying 1?methyl?3,4,5?trinitro?pyrazole synthesis[J].Yunnan Chemical Technology,2018,45(5):88-90.
[39] R Corte,I De LUCCA,T Fang,et al. Macrocycles with Hetrocy?clic P2′Groups as Factor Xia Inhibitors:WO2015116886 A1[P],2015.
[40] Ioannidis Stephanos,Talbot Adam Charles,Follows Bruce,et al. Pyrrolo and Pyrazolo?Pyrimidines as Ubiquitin?specific Pro?tease 7 Inhibitors:US2016185785A1[P],2016.
[41] Su Jin Han,Hyun Tae Kim,Jung Min Joo. Direct C?H alkenyl?ation of functionalized pyrazoles[J]. J Org Chem,2016,81:689-698.
[42] BiffinM E C,BrownDJ,PorterQ N. A novel route from 4?me?thoxy?5?nitropyrimi?nitropyrimi?dine to 3?amino?4?nitropyr?azole and pyrazolo[3,4?b]pyra?zine[J]. Terahedron Lett,1967,21(8):2029-2031.
[43] Biffin M E C,Brown D J,Porter Q N. Pyrimidine reactions.PartⅩⅧ. The conversion of 4?methoxy?5?nitropyri?mideine into3?amino?4?nitropyrazole by hydrazine[J]. J Chem Soc(C),1968,17:2159-2162.
[44] Shevelev S A,Vinogradov V M,Dalinger I L,et al. Nitropyr?azoles 8. 3(5)?amino?4?nitropyra?zoles:convenient synthesis and study of nitration[J].Russian Chemical Bulletin,1993,42(11):1861-1864.
[45] LatypovNV,SilevichVA,IvanovPA,et al. Diazotization ofami?nonitropyrazoles[J]. Chemistry of Hetero-cyclic Compounds,1976,12(12):1355-1359.
[46] Vinogradov V M,Cherkasova T I,Dalinger I L,et al. Nitropyr?azoles 5. Synthesis of substituted 3?nitropyra?zoles from 3?ami?no?4?cyanopyrazole[J]. Russian Chemical Bulletin,1993,42(9):1552-1554.
[47]汪营磊,姬月萍,葛忠学,等.一锅法合成3,4?二硝基吡唑.含能材料与钝感弹药技术学术研讨会论文集[C]//三亚,2012:172-175.WANG Ying?lei,JI Yue?ping,GE Zhong?xue,et al. Synthesis and Properties of 3,4?Dinitropyrazole. Symposium Proceed?ings of Energetic Materials and Insensitive Munitions Technolo?gy[C]//Sanya,2012:172-175.
[48]刘威,李永祥.3,4?二硝基吡唑合成工艺研究展望[J].江西化工,2015(5):8-12.LIU Wei,LI Yong?xiang. Prospect on studying 3,4?nitropyr?azole synthesis[J].Jiangxi Chemical Industry,2015(5):8-12.
[49] Stefan E K. Derivatives of 3(5),4?dinitropyrazole as potential energetic plasticisers[J].Chem Eng,2011,26(5):929-935.
[50] Ravi P,Koti Reddy C K,Saikia A,et al. Nitrodeiodination of polyiodopyrazoles[J]. Propellants,Explosives,Pyrotechnics,2012,37(2):167-171.
[51]田新.3,4?二硝基吡唑合成及性能研究[D].北京:中国工程物理研究院,2012.TIAN Xin. Improved synthesis of 3,4?dinitropyrazole[D]. Bei jing:China Academy of Engineer Physic,2012.
[52]田新,李金山.3,4?二硝基吡唑热分解及非等温动力学[J].化学研究与应用,2013,25(2):206-209.TIAN Xin,LI Jin?shan. Thermal decomposition and non?isother?mal kinetics of 3,4?dinitropyrazole[J].Chemical Research and Application,2013,25(2):206-209.
[53]杜闪.3,4?二硝基吡唑的合成及其性能研究[D].太原:中北大学,2012.DU Shan.Synthesis and properties of 3,4?dinitropyrazole[D].Taiyuan:North University of China,2012.
[54]杜闪,李永祥,王建龙,等.3,4?二硝基吡唑合成方法及性能研究综述[J].化学研究,2011,22(5):106-110.DU Shan,LI Yong?xiang,WANG Jian?long,et al. Review for synthetic method and properties of 3,4?dinitro?pyrazole[J].Chemical Research,2011,22(5):106-110.
[55]李永祥,曹端林,王建龙.三种新型低熔点炸药的合成及表征[J].兵工学报,2013,34(1):36-40.Li Yong?xiang,CAO Duan?lin,WANG Jian?long. Synthesis and characterization studies on novel three explosives with low melting point[J]. Journal of China Ordnance,2013,34(1):36-40.
[56]曹端林,李雅津,杜耀,等.熔铸炸药载体的研究评述[J].含能材料,2013,21(2):157?165.CAO Duan?lin,LI Ya?jin,DU Yao,et al. Review on carriers for melt?cast explosives[J]. Chinese Journal of Energetic Materials(Hanneng Cailiao),2013,21(2):157-165.
[57]张巧玲,李雅津,焦清介,等.1?甲基?3,4?二硝基吡唑合成与表征[J].含能材料,2015,23(3):222-225.ZHANG Qiao?ling,LI Ya?jin,JIAO Qing?jie,et al. Optim iza?tion on synthesis process and characterization of 1?methyl?3,4?dinitropyrazoles[J]. Chinese Journal of Energetic Materials(Hanneng Cailiao),2015,23(3)3:222-225.
[58]朱翔.微通道反应器中3,4?二硝基吡唑合成工艺研究[D].南京:南京理工大学,2017.ZHU Xiang.Study on the synthetical of 3,4?bisnitropyrazole in microreactor[D]. Nanjing:Nanjing University of Science&Technology,2017.
[59]汪营磊,张志忠,王伯周,等.3,5?二硝基吡唑合成研究[J].含能材料,2007,15(6):574-576.WANG Ying?lei,ZHANG Zhi?zhong,WANG Bo?zhou,et al.Synthesis of 3,5?dinitropyrazole[J].Chinese Journal of Energetic Materials(Hanneng Cailiao),2007,15(6):574?576.
[60]成健.不同硝化体系中3,5?二硝基吡唑的合成[D].南京:南京理工大学,2007.CHENG Jian. Synthesis of 3,5?Dinitropyrazole under different nitrification system[D].Nanjing:Nanjing University of Science and Technology,2007.
[61]周智明,陶文昌,章军.一种1?甲基?3,4,5?三硝基吡唑(MTNP)中间体3,5?二硝基吡唑的高选择性、高产率的无溶剂制备方法:CN105669557A[P],2016.ZHOU Zhi?ming,TAO Wen?chang,ZHANG Jun. High?selec?tivity and high?yield non?solvent preparation method of1?methyl?3,4,5?trinitropyrazole(MTNP)intermediate 3,5?di?nitropyrazole:CN105669557A[P],2016.
[62]刘伟,王建龙,曹端林,等.3,5?二硝基吡唑的合成工艺研究[J].应用化工,https://doi. org/10.16581/j. cnki. issn 1671?3206.20180330.084.LIU Wei,WANG Jian?long,CAO Duan?lin,et al. Synthesis of3,5?dinitropyrazole[J]. Applied Chemical Industry,https://doi.org/10.16581/j.cnki.issn 1671?3206.20180330.084.
[63] Katritzky A R.Physical methods in heterocyelic chemistry[M].New York:Academic Press,1974.
[64]李永祥,曹端林,王建龙,等.一种1?甲基?3,4?二硝基吡唑的制备方法:CN103467381A[P],2013.LI Yong?xiang,CAO Duan?lin,WANG Jian?long,et al. A prepa?ration method of 1?methyl?3,4?dinitropyrazole:CN103467381A[P],2013.
[65]李永祥,郭俊玲,宋磊,等.1?甲基?3,4?二硝基吡唑的合成、性能及晶体结构[J].火炸药学报,2015,38(3):64-68.LI Yong?xiang,GUO Jun?ling,SONG Lei,et al. Synthesis,per?formance and crystal structure of 1?methyl?3,4?dinitropyrazole[J]. Chinese Journal of Explosives&Propellants,2015,38(3):64-68.
[66] Zaitsev AA,DalingerI L,ShevelevS A.Dinitropyrazoles[J].Russian Chemical Reviews,2009,78(7):589-627.
[67] Schmidt R D,Lee G S,Pagoria P F. Synthesis and properties of a new explosive 4?amino?3,5?dinitro?1H?pyrazole(LLM?116),UCRL?ID?148510[R].Livermore:Lawrence Livermore National Laboratory,2001.
[68] Schmidt R D,Lee G S,Pagoria P F,et al. Sythesis of 4?amino?3,5?dinitro?1H?pyrazole using vicarious nucleophilic substitution of hydrogen[J].J Heterocyclic Chem,2001,38:1227-1230.
[69]汪营磊,张志忠,王伯周,等.VNS反应合成LLM?116[J].火炸药学报,2007,30(6):20-23.WANG Ying?lei,ZHANG Zhi?zhong,WANG Bo?zhou,et al.Synthesis of LLM?116 by VNS reaction[J]. Chinese Journal of Explosives&Propellants,2007,30(6):20-23.
[70] Stefan E K,Nikolaj V Latypova. Four syntheses of 4?amino?3,5?dinitropyrazole[J].Journal of Heterocyclic Chemistry,2014,51:1621-1627.
[71] Man Zhang,Huiqi Gao,Chuan Li,et al. Towards improved ex?plosives with a high performance:N?(3,5?dinitro?1H?pyr?azol?4?yl)?1H?tetrazol?5?amine and its salts[J]. J Mater Chem A,2017,5:1769-1777.
[72] Dalinger I L,Popova G P,Vatsadze I A,et al. Synthesis of 3,4,5?trinitropyrazole[J].Russ Chem Bul,2009,58(10):2185.
[73] Herve G. Dinitropyrazole derivatives,their preparation and en?ergetic compositions comorising them:US 8440839[P],2013.
[74] Stefan Ek,Nikolaj V Latypov. Four syntheses of 4?amino?3,5?dinitropyrazole[J].Journal of Heterocyclic Chemistry,2014,51(6):1621-1627.
[75] Herve G,Roussel C,Graindorge H. Selective preparation of 3,4,5?trinitro?1H?pyrazole:A stable all?carbon?nitrated arene[J].Angew Chem Int Ed,2010,49(18):3177-3181.
[76] Ravi P,Tewari S P. Solvent free microwave assisted isomeriza?tion of N?nitropyazoles[J]. Propellants,Explosives,Pyrotechnics,2013,38(1):147-151.
[77] Chuan Li,Man Zhang,Qishan Chen,et al. 1?(3,5?Dini?tro?1H?pyrazol?4?yl)?3?nitro?1H?1,2,4?triazol?5?amine(HCPT)and its energetic salts:highly thermally stable energetic materi?als with high?performance[J].Dalton Trans,2016,45:17956-17965.
[78] Zhao X,Zhang J C,Li S H,et al. A green and facile approach for synthesis of nitro heteroaromatics in water[J]. Organic Process Research&Development,2014,18(7):886-890
[79]赵秀秀.硝基唑类含能化合物的合成与反应性研究[D].北京:北京理工大学,2016.ZHAO Xiu?xiu. Synthesis and reactivity of nitrozoles energetic compounds[D].Beijing:Beijing Institute of Technology,2016.
[80]吴军鹏.3,4,5?三硝基吡唑的合成研究及其与苦基氯缩合反应探索[D].太原:中北大学,2017.WU Jun?peng. Study on synthesis of 3,4,5?trinitro?1H?pyr?azole and exploration its condensation reaction with picryl chloride[D].Taiyuan:North University of China,2017.
[81] Ravi P,Girish G M,Sikder A K,et al. Thermal decomposition kinetics of 1?methyl?3,4,5?trinitropyrzole[J]. Thermochimica Acta,2012,528(2):53-57.
[82] Ravi P,Tewari S P. Facile and environmentally friendly synthe?sis of nitropyrazoles using montmorillonite K?10 impregnated with bismuth nitrate[J]. Catalysis Communications,2012,19(19):37-41.
[83] Ravi P,Tewari S P.Faujasite catalyzed nitrodeiodination of io?dopyrazoles[J]. Catalysis Communications,2013,42(23):35-39.
[84] Dalinger I L,Vatsadze I A,Shkineva T K,et al. The specific re?activity of 3,4,5?trinitro?1H?pyrazole[J].Mendeleev Commun,2010,20(5):253-254.
[85] Dalinger I L,Vatsadze I A,Shkineva T K,et al. Synthesis and comparison of the reactivity of 3,4,5?1H?Trinitropyrazole and Its N?methyl derivative[J]. Journal of Heterocyclic Chemistry,2013,50(4):911-924.
[86]李雅津,曹端林,李永祥,等.1?甲基?3,4,5?三硝基吡唑的合成与表征[J].火炸药学报,2013,36(3):28-30.LI Ya?jin,CAO Duan?lin,LI Yong?xiang,et al. Synthesis and characterization of 1?methyl?3,4,5?trinitropyra?zoles[J]. Chinese Journal of Explosives&Propellants,2013,36(3):28-30.
[87]郭俊玲,李永祥,王建龙,等.1?甲基?3,4,5?三硝基吡啶的一步法合成及热性能[J].含能材料,2015,23(3):304-306.GUO Jun?ling,LI Yong?xiang,WANG Jian?long,et al. One?step synthesis and thermal behavior of 1?methy?3,4,5?trinitropyr?azole[J].Chinese Journal of Energetic Materials(Hanneng Cailiao),2015,23(3):304-306.
[88] Heng?jie Guo,Xin Dang,FengYang,et al. Solubility and ther?modynamic properties of a kind of explosives in four binary solvents[J].Journal of Molecular Liquids,2017,247:313-327.
[89]郭俊玲,李永祥,王建龙,等.超酸消化法合成1?甲基?3,4,5?三硝基吡吡唑[J].合成化学,2015,23(2):161-163.GUO Jun?ling,LI Yong?xiang,WANG Jian?long,et al. Synthesis of 1?Methl?3,4,5?trinitropyrazole by Nitration with Super Ac?ids[J]. Chinese Journal of Synthetic Chemistry,2015,23(2):161-163.
[90]吴霏,李永祥,郝彩丽,等.N2O5/发烟硫酸体系一步法合成1?甲基?3,4,5?三硝基吡唑[J].含能材料,2016,24(6):618-620.WU Fei,LI Yong?xiang,HAO Cai?li,et al. One Step Synthesis of MTNP with N2O5/oleum system[J]. Chinese Journal Energetic Materia(Hanneng Cailiao),2016,24(6):618-620.
[91]陶文昌.1?甲基?3,4,5?三硝基吡唑(MTNP)的制备及性能[D].北京:北京理工大学,2016.TAO Wen?chang.Preparation and Properties of 1?Methyl?3,4,5?Trinitropyrazole(MTNP)[D]. Beijing:Beijing Institute of Technology,2016.
[92]王军,景梅,张晓玉,等.硝基二唑炸药爆炸参数的经验计算(Ⅱ)[J].含能材料,2013,21(5):609-611.WANG Jun,JING Mei,ZHANG Xiao?yu,et al. Empirical calcu?lation of the explosive prameters of nitrodiazole explosives(Ⅱ)[J].Chinese Journal of Energetic Materials(Hanneng Cailiao),2013,21(5):609-611
[93] Drukenmuller I E,Klapotke T M,Morgenstern Y,et al. Metal salts of dinitro?,trinitropyrazole,and trinitroimi?dazole[J].Zeitschrift fur Anorganische und Allgemeine Chemie,2014,640(11):2139-2149.
[94]吴军鹏,曹端林,王建龙,等.3,4,5?三硝基吡唑及其衍生物的研究进展[J].含能材料,2016,24(11):1121-1130.WU Jun?peng,CAO Duan?lin,WANG Jian?long,et al. Progress on 3,4,5?trinitro?1H?pyrazole and its derivatives[J]. Chinese Journal of Energetic Materials(Hanneng Cailiao),2016,24(11):1121-1130.
[95] Y Zhang,Y Guo,Y H Joo,et al. 3,4,5?trinitropyrazole?based energetic salts[J]. Chemistry-a European Journal,2010,16(35):10778-10784.
[96] Yanqiang Zhang,Yangen Huang,Damon A. Parrish,et al.4?Amino?3,5?dinitropyrazolatesalts—highly insensitive ener?getic materials[J]. Journal of Materials Chemistry,2011,21,6891-6897.
[97] Ping Yin,Jiaheng Zhang,Chunlin H,et al. Polynitro?substituted pyrazoles and triazoles as potential energetic materials and oxi?dizers[J]. J Mater Chem A,2014(2):3200-3208.
[98] X X Zhao,S H Li,Y Wang,et al. Design and synthesis of ener?getic materials towards high density and positive oxygen bal?ance by N?dinitromethyl functionalization of nitroazoles[J]. J Mater Chem A,2016(4):5495-5504.
[99] Ya Jin Li,Yong Xiang Li,Yan Hong Wang,et al. Theoretical cal?culation of the detonation parameters of nitropyrazolesexplo?sives[J]. Advanced Materials Research,2014,853:395-400.
[100]Yalkowsky S H. Carnelley′s rule and the prediction of melting point[J]. Journal of Pharmaceutical Sciences,2014,103(9):2629-2634.
[101]闫涛,王建华,刘玉存,等.二唑类熔铸炸药载体的分子设计[J].含能材料,2016,24(2):202-208.YAN Tao,WANG Jian?hua,LIU Yu?cun,et al. Molecular de?sign of diazole carriers for melt?cast explosives[J]. Chinese Joumal of Energetic Materials(Hanneng Cailiao),2016,24(2):202-208.
[102]蒋涛,张晓玉,景梅,等.1?氨基?3,5?二硝基吡唑的合成、晶体结构及热性能[J].含能材料,2014,22(5):654?657.JIANG Tao,ZHANG Xiao?yu,JING Mei,et al. Synthesis,crys?tal structure and thermal property of 1?amino?3,5?dinitropyr?azole[J].Chinese Joumal of Energetic Materials(Hanneng Cailiao),2014,22(5):654-657.
[103]尹磊,张至斌,张建国,等.3,4?二硝基吡唑的晶体结构[J].含能材料,2016,24(10):965-968.YI Lei,ZHANG Zhi?bin,ZHANG Jian?guo,et al. Crystal Struc?ture of 3,4?Dinitropyrazole[J]. Chinese Joumal of Energetic Materials(Hanneng Cailiao),2016,24(10):965-968.
[104]杜闪,赵家乐,李永祥,等.熔铸炸药载体的研究进展及其性能比较[J].化工中间体,2011(6):32-35.DU Shan,ZHAO Jia?le,LI Yong?xiang,et al. Study progress on melt?cast explosives carriers and comparition of their perfor?mance[J].Chenmical Intermediate,2011(6):32-35.
[105]Reddy D,Surapaneni C R,Nathaniel Get al. Melt?cast explo?sive material:US7304164B1[P],2007.
[106]王伯周,汪营磊,张志忠,等.4?氨基?3,5?二硝基吡唑(LLM?116)缩合物的合成与表征[J].含能材料,2009,17(3):293-295.WANG BO?zhou,WANG Ying?lei,ZHANG Zhi?zhong,et al.Synthesis and characterization of 4?amino?3,5?dinitropyrazole(LLM?116)condensation products[J].Chinese Journal of Energetic Materials(Hanneng Cailiao),2009,17(3):293-295.
[2]杨克明,曹端林,李永祥,等.1?甲基?3,5?二硝基?1,2,4?三唑的合成及表征[J].含能材料,2011(6):501-504.YANG Ke?ming,CAO Duan?lin,LI Yong?xiang,et al. Synthesis and characterization of 1?methyl?3,5?dininitro?1,2,4?trazole[J].Chinese Journal of Energetic Materials(Hanneng Cailiao),2011(6):501-504.
[3]柴春鹏,甘志勇,李娜,等.3?硝基?1,2,4?三唑?5?酮银盐的合成和热分解性能[J].火炸药学报,2011,34(2):36-38.CHAI Chun?peng,GAN Zhi?yong,LI Na,et al. Synthesis and thermal decomposition behavior of 3?nitro?1,2,4?triazol?5?one silver salt[J]. Chinese Journal of Explosives&Propellants,2011,34(2):36-38.
[4]高红旭,赵凤起,胡荣祖,等.六硝基六氮杂异戊兹烷的热分解反应动力学参数和热安全性评估[J].火炸药学报,2013,36(5):41-48.GAO Hong?xu,ZHAO Feng?qi,HU Rong?zu,et al. Estimation of the kinetic parameters of thermal decomposition reaction and thermal safety on hexanitrohexaazaisowurtzitane[J]. Chinese Journal of Explosives&Propellants,2013,36(5):41-48.
[5]阳世清,徐松林,雷永鹏.氮杂环含能化合物的研究进展[J].含能材料,2006,14(6):475-484.YANG Shi?qing,XU Song?lin,LEI Yong?peng. The research progress of nitrogen heterocyclic compounds[J]. Chinese Journal of Energetic Materials(Hanneng Cailiao),2006,14(6):475-484.
[6] Agrawal J P,Hodgson R. Organic Chemistry of Explosives[M].John Wiley:New York,2007:294-296.
[7] Pagoria P F,Lee J S,Mitchell A R,et al.A review of energetic materials synthesis[J].ThermochimActa,2002,384:187.
[8] Larina L,Lopyrev L. Nitroazoles:Synthesis,Structure and Ap?plications[M].New York:Springer,2009.
[9]杨雨璋.多氮含能复合物的制备及其稳定性的研究[D].北京:北京理工大学,2016.YANG Yu?zhang.Study on the synthesis and stability of poly ni?trogen energetic compounds[D]. Beijing:Beijing Institute of Technology,2016.
[10]唐伟强,任慧,焦清介,等.3,4?二硝基吡唑的性能表征及应用[J].含能材料,2017,25(1):44-48.TANG Wei?qiang,REN Hui,JIAO Qing?jie,et al. Property char?acterization of 3,4?dinitropyrazole and its application[J].Chinese Journal of Energetic Materials(Hanneng Cailiao),2017,25(1):44-48.
[11] Dheeraj Kumar,Chunlin He,Lauren A. Mitchell,et al. Con?necting energetic nitropyrazole and aminotetrazole moieties with N,N′?ethylene bridges:A promising approach for fi ne tuning energetic properties[J].J Mater Chem A,2016,4(23):9220-9228.
[12] Nagarjuna Kommu,M Balaraju,Vikas D Ghule,et al.Synthetic manifestation of nitro substituted tetrazole?N?(hetero)aryl de?rivatives and energetic studies[J]. J. Mater. Chem. A,2017,5(16):7366-7371.
[13] Yongxing Tang,Dheeraj Kumar,Jean′ne M Shreeve. Balanc?ing excellent performance and high thermal stability in a dini?tropyrazole fused 1,2,3,4?tetrazine[J].J Am Chem Soc,2017,139(39):13684-13687.
[14] Depanjan Sarkar,Anirban Som,Thalappil Pradeep. Catalytic paper spray ionization mass spectrometry with metalnanotubes and the detection of 2,4,6?trinitrotoluene[J]. Anal Chem,2017,89(21):11378-11382.
[15]赵廷兴,李磊,董战,等.硝基唑类含能化合物的合成研究进展[J].有机化学,2013,34(2):304-315.ZHAO Ting?xing,LI Lei,DONG Zhan,et al. Research progress on the synthesis of energetic nitroazoles[J].Chinese Journal of Organic Chemistry,2013,34(2):304-315.
[16] Gao H,Shreeve J M. Azole?based energetic salts[J]. Chemical Reviews,2011,111(11):7377-7436.
[17]李翠屏,孙天旭,陈新志.3?硝基吡唑的合成[J].染料与染色,2004,41(3):168-169.LI Cui?ping,SUN Tian?xu,CHEN Xin?zhi. Synthesis of 3?nitro?pyrazole[J].Dyestuffsand Coloration,2004,41(3):168-169.
[18] Adrian Huang,Kellie Wo,So Yeun Christine Lee,et al. Regiose?lective synthesis, NMR, and crystallographic analysis of N1?substituted pyrazoles[J].J Org Chem,2017,82(17):8864-8872.
[19] Lahm G P,Cordova D,Barry J D. New and selective ryanodine receptor activators for insect control[J]. Bioorganic&Medicinal Chemistry,2009,17(12):4127-4133.
[20] Mowbray C E,Burt C,Corbau R,et al. Pyrazole NNRTIs 4:se?lection of UK?453,061(lersivirine)as adevelopment candidate[J]. Bioorganic and Medicinal Chemistry Letters,2009,19(20):5857-5860.
[21] Emma Cavero,Santiago Uriel,Pilar Romero,et al. Tetrahedral zinc complexes with liquid crystalline and luminescent proper?ties:interplay between nonconventional molecular shapes and supramolecular mesomorphic order[J]. JAmChemSoc,2007,129(37),11608-11618.
[22]王凤.5?氨基吡唑、1,2,4?吡唑膦衍生物及其CuⅡ、FeⅡ配合物的合成与结构研究[D].太原:山西师范大学,2014.WANG Feng. Synthesis and Structural Research of 5?Amino Pyrazole,1,2,4,?Diazaphospholes Derivatives and CuⅡ,FeⅡMetal Complese[D]:Taiyuan:Shanxi Normal University,2014.
[23] Janssen J W A M,Koeners H J. The preparation of 3(5)?nitre?pyrazoles by thermal rearran?gement of N?nitropyrazoles[J].J Org Chem,1973,38(10):1777-1782.
[24] Price D,Morris J. Synthesis of new energetic melt?pour candi?dates[C]//Insensitive Munitions and Energetic Materials Tech?nology Symposium,2009.
[25] Verbruggen R,Viehe H G. Cycloaddition with 2?chloro?1?nitro?ethelene[J].Chimia,1975,29(8):350-352.
[26]李洪丽,熊彬,姜俊,等.3?硝基吡唑及其盐类的合成与表征[J].火炸药学报,2007,31(2):102-108.LI Hong?li,XIONG Bin,JIANG Jun,et al. Synethsi and charac?terization of 3?nitropyrazole and its salts[J]. Chinese Journal of Explosives&Propellants,2007,31(2):102-108.
[27]田新,李金山,王军.3,4?二硝基吡唑的合成[J].合成化学,2012,20(1):117-122.TIAN Xin,LI Jin?shan,WANG Jun. Synthesis of 3,4?dinitropyr?azoles[J]. Chinese Journal of Synthetic Chemistry,2012,20(1):117-122.
[28] Hüttel R,Büchele F.Uber N?nitro?pyrazole[J].Chemische Berichte,1955,88(10):1586-1590.
[29] Kanishchev M I,Korneeva N V,Shevelev S A,et al. Nitropyr?azoles(Review)[M]. Plenum Publishing Corporation,1988:435-453.
[30] Rao E N,Ravi P,Tewari S P. Experimental and theoretical stud?ies on the structure and vibrational properties of nitropyrazoles[J].Journal of Molecular Structure,2013(1043):121-131.
[31] Ravi P. Experimental and DFT studies on the structure,infra?red and Raman spectral properties of dinitropyrazoles[J].Journal of Molecular Structure,2015,1079:433-447.
[32] Senomyx Inc,Karanewsky Donald S,Fotsing Joseph R,et al.Identification of human T2R receptors that respond to bitter compounds that elicit the bitter taste in compositions,and the use thereof in assays to identify compounds that inhibit(block)bitter taste in compositions and use thereof:US9247759[P],2016.
[33]李永祥,党鑫,曹端林,等.4?硝基吡唑的一锅两步法合成及其晶体结构[J].含能材料,2018,26(5):404 409.LI Yong?xiang,DANG Xin,CAO Duan?lin,et al. One?pot two steps synthesis of 4?nitropyrazole and its crystal structure[J].Chinese Joumal of Energetic Materials(Hanneng Cailiao),2018,26(5):404-409.
[34]郭俊玲,曹端林,王建龙,等.硝基吡唑类化合物的合成研究进展[J].含能材料,2014,22(6):872-879.GUO Jun?ling,CAO Duan?lin,WANG Jian?long,et al. Review on synthesis of nitropyrazoles[J]. Chinese Journal of Energetic Materials(Hanneng Cailiao),2014,22(6):872-879.
[35] Katritzky A R,Scriven E F V,Majumder S,et al. Direct nitration of five membered heterocycles[J]. Arkivoc(ⅲ),2005,36(10):179-191.
[36] Ravi P,Gore G M,Tewari S P,et al. A simple and environmen?tally benign nitration of pyrazoles by impregn nitration of pyr?azoles by impregnated bismuth nitrate[J].Journal of HeterocyclicChemistry,2013,50(6):1322-1327.
[37] J DONG,B ZHONG,H YUAN,et al.Alk kinase inhibitor,and preparation method and use thereof:WO 201580685 A1[P],2017.
[38]郭恒杰,曹端林,李永祥.1?甲基?3,4,5?三硝基吡唑合成工艺研究进展[J].云南化工,2018,45(5):88-90.GUO Heng?jie,CAO Duan?lin,LI Yong?xiang. Prospect on studying 1?methyl?3,4,5?trinitro?pyrazole synthesis[J].Yunnan Chemical Technology,2018,45(5):88-90.
[39] R Corte,I De LUCCA,T Fang,et al. Macrocycles with Hetrocy?clic P2′Groups as Factor Xia Inhibitors:WO2015116886 A1[P],2015.
[40] Ioannidis Stephanos,Talbot Adam Charles,Follows Bruce,et al. Pyrrolo and Pyrazolo?Pyrimidines as Ubiquitin?specific Pro?tease 7 Inhibitors:US2016185785A1[P],2016.
[41] Su Jin Han,Hyun Tae Kim,Jung Min Joo. Direct C?H alkenyl?ation of functionalized pyrazoles[J]. J Org Chem,2016,81:689-698.
[42] BiffinM E C,BrownDJ,PorterQ N. A novel route from 4?me?thoxy?5?nitropyrimi?nitropyrimi?dine to 3?amino?4?nitropyr?azole and pyrazolo[3,4?b]pyra?zine[J]. Terahedron Lett,1967,21(8):2029-2031.
[43] Biffin M E C,Brown D J,Porter Q N. Pyrimidine reactions.PartⅩⅧ. The conversion of 4?methoxy?5?nitropyri?mideine into3?amino?4?nitropyrazole by hydrazine[J]. J Chem Soc(C),1968,17:2159-2162.
[44] Shevelev S A,Vinogradov V M,Dalinger I L,et al. Nitropyr?azoles 8. 3(5)?amino?4?nitropyra?zoles:convenient synthesis and study of nitration[J].Russian Chemical Bulletin,1993,42(11):1861-1864.
[45] LatypovNV,SilevichVA,IvanovPA,et al. Diazotization ofami?nonitropyrazoles[J]. Chemistry of Hetero-cyclic Compounds,1976,12(12):1355-1359.
[46] Vinogradov V M,Cherkasova T I,Dalinger I L,et al. Nitropyr?azoles 5. Synthesis of substituted 3?nitropyra?zoles from 3?ami?no?4?cyanopyrazole[J]. Russian Chemical Bulletin,1993,42(9):1552-1554.
[47]汪营磊,姬月萍,葛忠学,等.一锅法合成3,4?二硝基吡唑.含能材料与钝感弹药技术学术研讨会论文集[C]//三亚,2012:172-175.WANG Ying?lei,JI Yue?ping,GE Zhong?xue,et al. Synthesis and Properties of 3,4?Dinitropyrazole. Symposium Proceed?ings of Energetic Materials and Insensitive Munitions Technolo?gy[C]//Sanya,2012:172-175.
[48]刘威,李永祥.3,4?二硝基吡唑合成工艺研究展望[J].江西化工,2015(5):8-12.LIU Wei,LI Yong?xiang. Prospect on studying 3,4?nitropyr?azole synthesis[J].Jiangxi Chemical Industry,2015(5):8-12.
[49] Stefan E K. Derivatives of 3(5),4?dinitropyrazole as potential energetic plasticisers[J].Chem Eng,2011,26(5):929-935.
[50] Ravi P,Koti Reddy C K,Saikia A,et al. Nitrodeiodination of polyiodopyrazoles[J]. Propellants,Explosives,Pyrotechnics,2012,37(2):167-171.
[51]田新.3,4?二硝基吡唑合成及性能研究[D].北京:中国工程物理研究院,2012.TIAN Xin. Improved synthesis of 3,4?dinitropyrazole[D]. Bei jing:China Academy of Engineer Physic,2012.
[52]田新,李金山.3,4?二硝基吡唑热分解及非等温动力学[J].化学研究与应用,2013,25(2):206-209.TIAN Xin,LI Jin?shan. Thermal decomposition and non?isother?mal kinetics of 3,4?dinitropyrazole[J].Chemical Research and Application,2013,25(2):206-209.
[53]杜闪.3,4?二硝基吡唑的合成及其性能研究[D].太原:中北大学,2012.DU Shan.Synthesis and properties of 3,4?dinitropyrazole[D].Taiyuan:North University of China,2012.
[54]杜闪,李永祥,王建龙,等.3,4?二硝基吡唑合成方法及性能研究综述[J].化学研究,2011,22(5):106-110.DU Shan,LI Yong?xiang,WANG Jian?long,et al. Review for synthetic method and properties of 3,4?dinitro?pyrazole[J].Chemical Research,2011,22(5):106-110.
[55]李永祥,曹端林,王建龙.三种新型低熔点炸药的合成及表征[J].兵工学报,2013,34(1):36-40.Li Yong?xiang,CAO Duan?lin,WANG Jian?long. Synthesis and characterization studies on novel three explosives with low melting point[J]. Journal of China Ordnance,2013,34(1):36-40.
[56]曹端林,李雅津,杜耀,等.熔铸炸药载体的研究评述[J].含能材料,2013,21(2):157?165.CAO Duan?lin,LI Ya?jin,DU Yao,et al. Review on carriers for melt?cast explosives[J]. Chinese Journal of Energetic Materials(Hanneng Cailiao),2013,21(2):157-165.
[57]张巧玲,李雅津,焦清介,等.1?甲基?3,4?二硝基吡唑合成与表征[J].含能材料,2015,23(3):222-225.ZHANG Qiao?ling,LI Ya?jin,JIAO Qing?jie,et al. Optim iza?tion on synthesis process and characterization of 1?methyl?3,4?dinitropyrazoles[J]. Chinese Journal of Energetic Materials(Hanneng Cailiao),2015,23(3)3:222-225.
[58]朱翔.微通道反应器中3,4?二硝基吡唑合成工艺研究[D].南京:南京理工大学,2017.ZHU Xiang.Study on the synthetical of 3,4?bisnitropyrazole in microreactor[D]. Nanjing:Nanjing University of Science&Technology,2017.
[59]汪营磊,张志忠,王伯周,等.3,5?二硝基吡唑合成研究[J].含能材料,2007,15(6):574-576.WANG Ying?lei,ZHANG Zhi?zhong,WANG Bo?zhou,et al.Synthesis of 3,5?dinitropyrazole[J].Chinese Journal of Energetic Materials(Hanneng Cailiao),2007,15(6):574?576.
[60]成健.不同硝化体系中3,5?二硝基吡唑的合成[D].南京:南京理工大学,2007.CHENG Jian. Synthesis of 3,5?Dinitropyrazole under different nitrification system[D].Nanjing:Nanjing University of Science and Technology,2007.
[61]周智明,陶文昌,章军.一种1?甲基?3,4,5?三硝基吡唑(MTNP)中间体3,5?二硝基吡唑的高选择性、高产率的无溶剂制备方法:CN105669557A[P],2016.ZHOU Zhi?ming,TAO Wen?chang,ZHANG Jun. High?selec?tivity and high?yield non?solvent preparation method of1?methyl?3,4,5?trinitropyrazole(MTNP)intermediate 3,5?di?nitropyrazole:CN105669557A[P],2016.
[62]刘伟,王建龙,曹端林,等.3,5?二硝基吡唑的合成工艺研究[J].应用化工,https://doi. org/10.16581/j. cnki. issn 1671?3206.20180330.084.LIU Wei,WANG Jian?long,CAO Duan?lin,et al. Synthesis of3,5?dinitropyrazole[J]. Applied Chemical Industry,https://doi.org/10.16581/j.cnki.issn 1671?3206.20180330.084.
[63] Katritzky A R.Physical methods in heterocyelic chemistry[M].New York:Academic Press,1974.
[64]李永祥,曹端林,王建龙,等.一种1?甲基?3,4?二硝基吡唑的制备方法:CN103467381A[P],2013.LI Yong?xiang,CAO Duan?lin,WANG Jian?long,et al. A prepa?ration method of 1?methyl?3,4?dinitropyrazole:CN103467381A[P],2013.
[65]李永祥,郭俊玲,宋磊,等.1?甲基?3,4?二硝基吡唑的合成、性能及晶体结构[J].火炸药学报,2015,38(3):64-68.LI Yong?xiang,GUO Jun?ling,SONG Lei,et al. Synthesis,per?formance and crystal structure of 1?methyl?3,4?dinitropyrazole[J]. Chinese Journal of Explosives&Propellants,2015,38(3):64-68.
[66] Zaitsev AA,DalingerI L,ShevelevS A.Dinitropyrazoles[J].Russian Chemical Reviews,2009,78(7):589-627.
[67] Schmidt R D,Lee G S,Pagoria P F. Synthesis and properties of a new explosive 4?amino?3,5?dinitro?1H?pyrazole(LLM?116),UCRL?ID?148510[R].Livermore:Lawrence Livermore National Laboratory,2001.
[68] Schmidt R D,Lee G S,Pagoria P F,et al. Sythesis of 4?amino?3,5?dinitro?1H?pyrazole using vicarious nucleophilic substitution of hydrogen[J].J Heterocyclic Chem,2001,38:1227-1230.
[69]汪营磊,张志忠,王伯周,等.VNS反应合成LLM?116[J].火炸药学报,2007,30(6):20-23.WANG Ying?lei,ZHANG Zhi?zhong,WANG Bo?zhou,et al.Synthesis of LLM?116 by VNS reaction[J]. Chinese Journal of Explosives&Propellants,2007,30(6):20-23.
[70] Stefan E K,Nikolaj V Latypova. Four syntheses of 4?amino?3,5?dinitropyrazole[J].Journal of Heterocyclic Chemistry,2014,51:1621-1627.
[71] Man Zhang,Huiqi Gao,Chuan Li,et al. Towards improved ex?plosives with a high performance:N?(3,5?dinitro?1H?pyr?azol?4?yl)?1H?tetrazol?5?amine and its salts[J]. J Mater Chem A,2017,5:1769-1777.
[72] Dalinger I L,Popova G P,Vatsadze I A,et al. Synthesis of 3,4,5?trinitropyrazole[J].Russ Chem Bul,2009,58(10):2185.
[73] Herve G. Dinitropyrazole derivatives,their preparation and en?ergetic compositions comorising them:US 8440839[P],2013.
[74] Stefan Ek,Nikolaj V Latypov. Four syntheses of 4?amino?3,5?dinitropyrazole[J].Journal of Heterocyclic Chemistry,2014,51(6):1621-1627.
[75] Herve G,Roussel C,Graindorge H. Selective preparation of 3,4,5?trinitro?1H?pyrazole:A stable all?carbon?nitrated arene[J].Angew Chem Int Ed,2010,49(18):3177-3181.
[76] Ravi P,Tewari S P. Solvent free microwave assisted isomeriza?tion of N?nitropyazoles[J]. Propellants,Explosives,Pyrotechnics,2013,38(1):147-151.
[77] Chuan Li,Man Zhang,Qishan Chen,et al. 1?(3,5?Dini?tro?1H?pyrazol?4?yl)?3?nitro?1H?1,2,4?triazol?5?amine(HCPT)and its energetic salts:highly thermally stable energetic materi?als with high?performance[J].Dalton Trans,2016,45:17956-17965.
[78] Zhao X,Zhang J C,Li S H,et al. A green and facile approach for synthesis of nitro heteroaromatics in water[J]. Organic Process Research&Development,2014,18(7):886-890
[79]赵秀秀.硝基唑类含能化合物的合成与反应性研究[D].北京:北京理工大学,2016.ZHAO Xiu?xiu. Synthesis and reactivity of nitrozoles energetic compounds[D].Beijing:Beijing Institute of Technology,2016.
[80]吴军鹏.3,4,5?三硝基吡唑的合成研究及其与苦基氯缩合反应探索[D].太原:中北大学,2017.WU Jun?peng. Study on synthesis of 3,4,5?trinitro?1H?pyr?azole and exploration its condensation reaction with picryl chloride[D].Taiyuan:North University of China,2017.
[81] Ravi P,Girish G M,Sikder A K,et al. Thermal decomposition kinetics of 1?methyl?3,4,5?trinitropyrzole[J]. Thermochimica Acta,2012,528(2):53-57.
[82] Ravi P,Tewari S P. Facile and environmentally friendly synthe?sis of nitropyrazoles using montmorillonite K?10 impregnated with bismuth nitrate[J]. Catalysis Communications,2012,19(19):37-41.
[83] Ravi P,Tewari S P.Faujasite catalyzed nitrodeiodination of io?dopyrazoles[J]. Catalysis Communications,2013,42(23):35-39.
[84] Dalinger I L,Vatsadze I A,Shkineva T K,et al. The specific re?activity of 3,4,5?trinitro?1H?pyrazole[J].Mendeleev Commun,2010,20(5):253-254.
[85] Dalinger I L,Vatsadze I A,Shkineva T K,et al. Synthesis and comparison of the reactivity of 3,4,5?1H?Trinitropyrazole and Its N?methyl derivative[J]. Journal of Heterocyclic Chemistry,2013,50(4):911-924.
[86]李雅津,曹端林,李永祥,等.1?甲基?3,4,5?三硝基吡唑的合成与表征[J].火炸药学报,2013,36(3):28-30.LI Ya?jin,CAO Duan?lin,LI Yong?xiang,et al. Synthesis and characterization of 1?methyl?3,4,5?trinitropyra?zoles[J]. Chinese Journal of Explosives&Propellants,2013,36(3):28-30.
[87]郭俊玲,李永祥,王建龙,等.1?甲基?3,4,5?三硝基吡啶的一步法合成及热性能[J].含能材料,2015,23(3):304-306.GUO Jun?ling,LI Yong?xiang,WANG Jian?long,et al. One?step synthesis and thermal behavior of 1?methy?3,4,5?trinitropyr?azole[J].Chinese Journal of Energetic Materials(Hanneng Cailiao),2015,23(3):304-306.
[88] Heng?jie Guo,Xin Dang,FengYang,et al. Solubility and ther?modynamic properties of a kind of explosives in four binary solvents[J].Journal of Molecular Liquids,2017,247:313-327.
[89]郭俊玲,李永祥,王建龙,等.超酸消化法合成1?甲基?3,4,5?三硝基吡吡唑[J].合成化学,2015,23(2):161-163.GUO Jun?ling,LI Yong?xiang,WANG Jian?long,et al. Synthesis of 1?Methl?3,4,5?trinitropyrazole by Nitration with Super Ac?ids[J]. Chinese Journal of Synthetic Chemistry,2015,23(2):161-163.
[90]吴霏,李永祥,郝彩丽,等.N2O5/发烟硫酸体系一步法合成1?甲基?3,4,5?三硝基吡唑[J].含能材料,2016,24(6):618-620.WU Fei,LI Yong?xiang,HAO Cai?li,et al. One Step Synthesis of MTNP with N2O5/oleum system[J]. Chinese Journal Energetic Materia(Hanneng Cailiao),2016,24(6):618-620.
[91]陶文昌.1?甲基?3,4,5?三硝基吡唑(MTNP)的制备及性能[D].北京:北京理工大学,2016.TAO Wen?chang.Preparation and Properties of 1?Methyl?3,4,5?Trinitropyrazole(MTNP)[D]. Beijing:Beijing Institute of Technology,2016.
[92]王军,景梅,张晓玉,等.硝基二唑炸药爆炸参数的经验计算(Ⅱ)[J].含能材料,2013,21(5):609-611.WANG Jun,JING Mei,ZHANG Xiao?yu,et al. Empirical calcu?lation of the explosive prameters of nitrodiazole explosives(Ⅱ)[J].Chinese Journal of Energetic Materials(Hanneng Cailiao),2013,21(5):609-611
[93] Drukenmuller I E,Klapotke T M,Morgenstern Y,et al. Metal salts of dinitro?,trinitropyrazole,and trinitroimi?dazole[J].Zeitschrift fur Anorganische und Allgemeine Chemie,2014,640(11):2139-2149.
[94]吴军鹏,曹端林,王建龙,等.3,4,5?三硝基吡唑及其衍生物的研究进展[J].含能材料,2016,24(11):1121-1130.WU Jun?peng,CAO Duan?lin,WANG Jian?long,et al. Progress on 3,4,5?trinitro?1H?pyrazole and its derivatives[J]. Chinese Journal of Energetic Materials(Hanneng Cailiao),2016,24(11):1121-1130.
[95] Y Zhang,Y Guo,Y H Joo,et al. 3,4,5?trinitropyrazole?based energetic salts[J]. Chemistry-a European Journal,2010,16(35):10778-10784.
[96] Yanqiang Zhang,Yangen Huang,Damon A. Parrish,et al.4?Amino?3,5?dinitropyrazolatesalts—highly insensitive ener?getic materials[J]. Journal of Materials Chemistry,2011,21,6891-6897.
[97] Ping Yin,Jiaheng Zhang,Chunlin H,et al. Polynitro?substituted pyrazoles and triazoles as potential energetic materials and oxi?dizers[J]. J Mater Chem A,2014(2):3200-3208.
[98] X X Zhao,S H Li,Y Wang,et al. Design and synthesis of ener?getic materials towards high density and positive oxygen bal?ance by N?dinitromethyl functionalization of nitroazoles[J]. J Mater Chem A,2016(4):5495-5504.
[99] Ya Jin Li,Yong Xiang Li,Yan Hong Wang,et al. Theoretical cal?culation of the detonation parameters of nitropyrazolesexplo?sives[J]. Advanced Materials Research,2014,853:395-400.
[100]Yalkowsky S H. Carnelley′s rule and the prediction of melting point[J]. Journal of Pharmaceutical Sciences,2014,103(9):2629-2634.
[101]闫涛,王建华,刘玉存,等.二唑类熔铸炸药载体的分子设计[J].含能材料,2016,24(2):202-208.YAN Tao,WANG Jian?hua,LIU Yu?cun,et al. Molecular de?sign of diazole carriers for melt?cast explosives[J]. Chinese Joumal of Energetic Materials(Hanneng Cailiao),2016,24(2):202-208.
[102]蒋涛,张晓玉,景梅,等.1?氨基?3,5?二硝基吡唑的合成、晶体结构及热性能[J].含能材料,2014,22(5):654?657.JIANG Tao,ZHANG Xiao?yu,JING Mei,et al. Synthesis,crys?tal structure and thermal property of 1?amino?3,5?dinitropyr?azole[J].Chinese Joumal of Energetic Materials(Hanneng Cailiao),2014,22(5):654-657.
[103]尹磊,张至斌,张建国,等.3,4?二硝基吡唑的晶体结构[J].含能材料,2016,24(10):965-968.YI Lei,ZHANG Zhi?bin,ZHANG Jian?guo,et al. Crystal Struc?ture of 3,4?Dinitropyrazole[J]. Chinese Joumal of Energetic Materials(Hanneng Cailiao),2016,24(10):965-968.
[104]杜闪,赵家乐,李永祥,等.熔铸炸药载体的研究进展及其性能比较[J].化工中间体,2011(6):32-35.DU Shan,ZHAO Jia?le,LI Yong?xiang,et al. Study progress on melt?cast explosives carriers and comparition of their perfor?mance[J].Chenmical Intermediate,2011(6):32-35.
[105]Reddy D,Surapaneni C R,Nathaniel Get al. Melt?cast explo?sive material:US7304164B1[P],2007.
[106]王伯周,汪营磊,张志忠,等.4?氨基?3,5?二硝基吡唑(LLM?116)缩合物的合成与表征[J].含能材料,2009,17(3):293-295.WANG BO?zhou,WANG Ying?lei,ZHANG Zhi?zhong,et al.Synthesis and characterization of 4?amino?3,5?dinitropyrazole(LLM?116)condensation products[J].Chinese Journal of Energetic Materials(Hanneng Cailiao),2009,17(3):293-295.