新型臂式冠醚的研究及抗氧剂的合成
|
摘要
冠醚是一类人工合成的受体,人们经过几十年的研究,仍然方兴未艾。如何设计对单一金属离子具有高选择性的冠醚,一直是人们所面临的具有挑战性的课题。本论文第一部分以2-甲基苯并噁唑、邻苯二酚、氯乙醇、苯胺和三甘醇为初始原料设计合成了5种冠醚——2,3,11,12-二苯并-1,4,7,10,13,16-六氧杂环十八碳-2,11-二烯,二(4’-甲酰基)-2,3,11,12-二苯并-1,4,7,10,13,16-六氧杂环十八碳-2,11-二烯,二{4’-[2-(2-苯并噁唑基)乙烯基]}-2,3,11,12-二苯并-1,4,7,10,13,16-六氧杂环十八碳-2,11-二烯,7,16-二苯-1,4,10,13-四氧杂-7,16-六氧杂环十八烷,N,N’-二(4’-甲酰苯基)-7,16-二苯-1,4,10,13-四氧杂-7,16-二氮杂环十八烷。其中二{4’-[2-(2-苯并噁唑基)乙烯基]}-2,3,11,12-二苯并-1,4,7,10,13,16-六氧杂环十八碳-2,11-二烯是未经文献报道的新化合物。我们在冠醚的苯环上接上了带有杂原子的较大的共轭体系,目的是改变母体冠醚的光物理性能,通过研究其结合阳离子后光谱的变化规律进一步研究新型冠醚化合物对碱金属和碱土金属离子的配位及识别性能。我们预期它们在构筑冠醚-金属配位聚合物时,将会产生π-π堆积、阳离子-π相互作用等超分子构筑力,从而组装成为结构新颖的超分子物种。本文通过熔点测定、核磁共振氢谱分析表征了化合物的结构。用荧光光谱的方法初步研究了新型冠醚化合物对碱金属和碱土金属离子的配位及识别性能。
本论文第二部分以高哌嗪、4-羟基苯甲酸和6-羟基-2-萘甲酸为原料合成了一种高哌嗪不对称双酰胺类抗氧剂,这个化合物以前没有文献报道过,并通过核磁共振氢谱表征了化合物的结构。
Crown ether is a kind of man-made receptor, and its study is still of ongoing interest for more than thirty years. It is a challengible task for researchers to design more highly selective crown ether for single metal ions. In the first part of this thesis, Five crown ethers were synthesized by using 2-methylbenzo[d]oxazole, pyrocatechol, 2-chloroethanol, aniline and triethylene glycol. They are 2,3,11,12-dibenzo-1,4,7,10, 13,16-hexaoxacyclooctadeca-2,11-diene, bis(4'-formyl)-2,3,11,12-dibenzo-1,4,7,10,13, 16-hexaoxacyclooctadeca-2,11-diene, bis{4’-[2-(2-benzooxazolyl)ethenyl]}-2,3,11,12 -dibenzo-1,4,7,10,13,16-hexaoxacyclooctadeca-2,11-diene, 7,16-diphenyl-1,4,10,13- tetraoxa-7,16-diaza-cyclooctadecane, N,N'-bis(4-formyl)-7,16-diphenyl-1,4,10,13- tetraoxa-7,16-diaza-cyclooctadecane. Bis{4’-[2-(2-benzooxazolyl)ethenyl]}-2,3,11,12 -dibenzo-1,4,7,10,13,16-hexaoxacyclooctadeca-2,11-diene is new. In order to improve the electronic spectra properties of the crown ether, efficient conjugatingπ-πgroup is connected with the benzene ring. The recognization ability with alkali metals and alkali earth metals was investigated via the spectra changing after the above metal cations are combined. It was expected that novel non-covalent forces in crystal such asπ-πstacking, cation-πinteractions and so on would aid the formation of supramolecular aggregation when those crown ethers coordinate with metal cations. These compounds were determined by melting point and 1H-NMR. Through fluorescence spectrum method, we primarily study on the linkage and selectivity of novel armed crown ethers-metal.
In the second part, asymmetric diamide of homopiperazine was synthesized by using homopiperazine, 4-hydroxybenzoic acid and 6-hydroxynaph-thalene-2- carboxylic acid, this compound is new. Its structure was determined by 1H-NMR.
本论文第二部分以高哌嗪、4-羟基苯甲酸和6-羟基-2-萘甲酸为原料合成了一种高哌嗪不对称双酰胺类抗氧剂,这个化合物以前没有文献报道过,并通过核磁共振氢谱表征了化合物的结构。
Crown ether is a kind of man-made receptor, and its study is still of ongoing interest for more than thirty years. It is a challengible task for researchers to design more highly selective crown ether for single metal ions. In the first part of this thesis, Five crown ethers were synthesized by using 2-methylbenzo[d]oxazole, pyrocatechol, 2-chloroethanol, aniline and triethylene glycol. They are 2,3,11,12-dibenzo-1,4,7,10, 13,16-hexaoxacyclooctadeca-2,11-diene, bis(4'-formyl)-2,3,11,12-dibenzo-1,4,7,10,13, 16-hexaoxacyclooctadeca-2,11-diene, bis{4’-[2-(2-benzooxazolyl)ethenyl]}-2,3,11,12 -dibenzo-1,4,7,10,13,16-hexaoxacyclooctadeca-2,11-diene, 7,16-diphenyl-1,4,10,13- tetraoxa-7,16-diaza-cyclooctadecane, N,N'-bis(4-formyl)-7,16-diphenyl-1,4,10,13- tetraoxa-7,16-diaza-cyclooctadecane. Bis{4’-[2-(2-benzooxazolyl)ethenyl]}-2,3,11,12 -dibenzo-1,4,7,10,13,16-hexaoxacyclooctadeca-2,11-diene is new. In order to improve the electronic spectra properties of the crown ether, efficient conjugatingπ-πgroup is connected with the benzene ring. The recognization ability with alkali metals and alkali earth metals was investigated via the spectra changing after the above metal cations are combined. It was expected that novel non-covalent forces in crystal such asπ-πstacking, cation-πinteractions and so on would aid the formation of supramolecular aggregation when those crown ethers coordinate with metal cations. These compounds were determined by melting point and 1H-NMR. Through fluorescence spectrum method, we primarily study on the linkage and selectivity of novel armed crown ethers-metal.
In the second part, asymmetric diamide of homopiperazine was synthesized by using homopiperazine, 4-hydroxybenzoic acid and 6-hydroxynaph-thalene-2- carboxylic acid, this compound is new. Its structure was determined by 1H-NMR.
引文
[1] Pedersen C. J., Cyclic polyethers and their complexes with metal salts, J. Am. Chem. Soc., 1967, 89(10): 2495-2496
[2] Pedersen C. J., Crystalline salt complexes of macrocyclic polyethers, J. Am. Chem. Soc., 1970, 92(2): 386-391
[3] Dietrich B., Lehn J. M. and Sauvage J. P., Diaza-polyoxa-macrocycles et macrobic -ycles, Tetrahedron Lett., 10(34): 2885-2888
[4] Donald J. Cram, the Design of molecular hosts, guests, and their complexes, J. Angew. Chem., Int. Ed., 1988, 27(8): 1009-1020
[5] Bornet C., Amardeil R. and Meunier P., Structural and complexation properties of diselenacrown ethers. Synthesis and crystal structure of cationic palladium tetraselena complex, J.Chem. Soc., Dalton Trans., 1999, 7: 1039-1040
[6] Levason W., Quirk J. J., Selenoether Macrocyclic complexes of platinum(Ⅳ): synthesis and spectroscopic studies of [Pt([16]aneSe4)X2[PF6]2 (X=Cl, Br), X-ray structure of [Pt([16]aneSe4)Cl2[PF6]2, Inorg. Chem., 1994, 33(6): 6120-6122
[7]刘育,张衡益等,冠醚的分子设计及其识别性质研究进展,有机化学, 2002, 22 (2): 91-100
[8]胡旭波,钟振林,卢雪然等,杯环冠醚研究进展,化学通报, 1997, 4: 18-25
[9]高明章,杨奕群等,手性冠醚的研究进展,有机化学, 2001, 21(7): 477-484
[10]李卫平,刘秀芳,徐汉生等,硒杂冠醚的研究进展,化学通报, 1995, 7: 7-14
[11] Stock H. T., Kellogg R. M., Synthesis of enantiomerically pure thiocrown ethers derived from 1, 1'-binaphthalene-2, 2'-diol, J. Org. Chem., 1996, 61(9): 3093- 3105
[12]徐汉生,李卫平,刘秀芳等,碲杂冠醚及其铂配合物的合成,化学学报, 1994, 52(4): 386-390
[13] Atwood J. L., Dawies J. E. D., MacNicol D. D., Inclusion Compounds, New York, Acaedemic Press, 1984
[14] Szejtli J., Cyclodextrin and Their Inclusion Complexes, Budapest, Akademiai Kiado, 1982
[15] Patai S., Rappoport Z. Eds., Crown Ethers and Analogs, Chichester, John Wiley& Sons, 1989
[16] Pedersen C. J., Cyclic polyethers and their complexes with metal salts, J. Am. Chem. Soc., 1967, 89(26): 7017-7036
[17]刘育,尤长城,张衡益等,超分子化学-合成受体的分子识别与组装,天津,南开大学出版社, 2001年
[18] Pedersen C. J., Frenssdorff H K., Macrocyclic polyethers and their complexes, Angew. Chem. Int Ed., 1972, 11(1):16-25
[19] Dietrich B, Viout P, Lehn J-M., Macrocyclic chemistry-aspects of organic and inorganic supramolecular chemistry, New York, VCH, 1993
[20]韩建荣,张衡益和刘育,双臂式苯并-15-冠-5的合成及其对金属离子的选择键合,高等学校化学学报, 2005, 26(7): 1273-1276
[21] Pedersen C. J., Cyclic polyethers and their complexes with metal salts, J. Am. Chem. Soc., 1967, 89(10): 2495-2496
[22] Brown M. D., William L. and David C. M., Primary and secondary coordination of crown ethers to scandium(III). Synthesis, properties and structures of the reaction products of ScCl3(thf)3, ScCl3·6H2O and Sc(NO3)3·5H2O with crown ethers, J.Chem.Soc., Dalton Trans., 2003, 5: 857-865
[23]萨如拉,多酸-冠醚超分子配合物的合成及其性质研究,硕士学位论文,首都师范大学, 2006年
[24] Timko J. M., Moore s. s., Walba D.M. et al., Host-guest complexation. 2. Structural units that control association constants between polyethers and tert-butylammonium salts, J. Am. Chem. Soc., 1977, 99(13): 4207-4219
[25]张伯生,魏俊发等,光谱实验室,二苯并18-冠-6配合物[NH4(DB18-C-6)]2[Pd(SCN)4]的合成与结构分析, 2003, 4: 73-76
[26]董文魁,杨汝栋,稀土(Ш)(4',5'-二溴苯并-15-冠-5)配合物的制备及表征,兰州大学学报(自然科学版), 2000, 36(2): 48-53
[27]贺媛,魏俊发,窦建民等,光谱实验室, [Na(15-C-5)]2[Pd(SCN)4]配合物的合成与结构分析, 2003, 5: 86-88
[28]于洪利,张尊听,窦建民等,光谱实验室, Na(18-C-6)]2[Cu(i-mnt)2]的合成与结构分析, 2003, 4: 81-83
[29] Dou J. M., Gao X. K. and Dong F. Y., One- or two-dimensional 2,3-naphtho crown ether complexes [Na(N15C5)]2[M(SCN)4] and [K(N18C6)]2 [M(SCN)4] (M = Pd, Pt) constructed byπ-πstacking interactions, J. Chem. Soc., Dalton Trans., 2004, 18: 2918-2922
[30] Neier R. and Trojanowski C., Reduces polyoxomolybdates with the Keggin and Dawson structures: preparation and crystal structures of two-electron reduced [K(18-crown-6)]2[N(pph3)2]2[HPMo12O40] 8MeCN·18-crown-6 and four- electron reduced [NBun4]5-[H3S2Mo18O62]·4MeCN(18-crown-6=1,4,7,10, 13,16- hexaoxacyclooctade cane), J. Chem. Soc., Dalton Trans., 1995, 15: 2521-2533
[31] You W. S., Wang E. B. and Zhang H., Synthesis and structural characterization of a new supermolecular compound: H3PW12O40·6C14H20O5·16H2O (C14H20O5= benzo-15-crown-5), J. Mol. Struct., 2000, 554: 141-147
[32] W. S. You and E. B. Wang, Sythesis and crystal structure of a new supermolecular compound: [C12H24O6][H3PMo12O40]·22H2O(C12H24O6=18- crown-6), J. Mol. Struct., 2000, 524: 133-139
[33]鲁晓明,宗瑞发,刘顺成等,苯基氮杂-15-冠-5对钼同多酸以及钨钼杂多酸阴离子的选择,高等学校化学学报[J], 1997, 18(12): 1911-1916
[34] Tokuyama Soda Co., Schiff base-type benzocrown ether, JP60130584, 1985-07- 12
[35] Tokuyama Soda Co., Schiff base-type benzocrown ether, JP60130585, 1985-07- 12
[36] Yam V. W. W., Wong K. M. C. and Lee V. W.-M., Synthesis, photophysis, ion-binding, studies and structural characterization of organometallics rhenium(?) crown complexes, Organometallics, 1995, 14(9): 4034-4036
[37]张来新,杨琼,新取代冠醚及其缩氨硫脲和缩氨脲化合物的合成,新疆大学学报(自然科学版), 2001, 1: 70-73
[38]张来新,杨琼, 4′-甲酰缩氨(硫)脲苯并15冠5的合成,吉首大学学报(自然科学版), 2001, 3: 86-87
[39] Liu Y., Zhang H. Y., Bai X. P., Molecular design of crown ethers. 21. Synthesis of novel double-armed benzo-15-crown-5 lariats and their complexation thermo -dynamics with light lanthanoid nitrates in acetonitrile, J. Org. Chem., 2000, 65(21): 7105-7109
[40] Thomas W. B., George M. L. and Hideo N., Host-guest complexation. 25. Effects of substituents on the complexing properties of chorands, J. Org. Chem., 1983, 48(24): 4728-4734
[41] Green R. N., 18-crown-6: a strong complexing agent for alkali metal cations, Tetrahedron Lett., 1972, 13(18): 1793-1796
[42]吴成泰,鲁天保,中国化学会第一届应用化学学术讨论会,北京, 1985
[43] DU PONT, Macrocyclic heter imine complexing agents, US3847949, 1974-11- 12
[44] Pedersen C. J., Macrocyclic polyether sulfides, J. Org. Chem., 1971, 36(2), 254-257
[45]陈立钦,汪玉庭,黄载福,硫杂冠醚的合成,有机化学, 1990, 10(6): 546-549
[46]陈立钦,汪玉庭,黄载福,苯并硫冠醚的DSC研究,武汉化工学院学报, 1997, 19(4): 5-8
[47] Higuchi H., Tani K. and Otsubl T., New synthetic method of [2.2] cyclophanes via diselena [3.3] cyclophanes, Bull. Chem. Soc. Jpn., 1987, 60(11): 4027-4036
[48] Kumagai T., Preparation of novel selenacrown ethers and their complexing abililties with transition metal and heavy matal cations, Chem. lett., 1989, 213(9): 1667-1670
[49]徐汉生,李卫平,刘秀芳等,硒杂冠醚的合成及其络合性能研究,有机化学, 1993, 13(1): 52-57
[50] Hashem Sharghi, Khodabakhsh Niknam and Maryam Pooyan, The halogen–med -iated opening of epoxides in the presence of pyridine-containing macrocycles, Tetrahedron, 2001, 57(28): 6057-6064
[51] Pedersen C. J., Cyclic polyethers and their complexes with metal salts, J. Am. Chem. Soc., 1967, 89(26): 7017-7036
[52] Julia L. B., Anton K., Christian T. et al., On the development of sensor molecules that display FeШ-amplified fluorescence, J. Am. Chem. Soc., 2005, 127(39): 13522-13529
[53] Junichi Ishikama, Hidefumr Sakamoto and Tamao Mizuno, Hydrazones derived from dithiamonoaza and tetrathiamonoaza analogs of polyethers as silver ion selective ionophore: Syntheses, Proton-Dissociation fehaviors, and metal ion complexing properties in 1,4-dioxane-water acidic solution, Bull. Chem. Soc. Jpn., 1995, 68: 3071-3076
[54]徐强,宋仲容,陈凤鸣, 2,6-二甲酰基-4-甲基苯酚合成方法的改进,西南民族大学学报(自然科学版), 2005, 31(4): 525-526
[55] Shohreh Ghorbanian, Lina K. Mehta and John Parrick, Synthesis of some 24-membered tetralactam derivatives by an unexpectedly simple route, and some macrocyclic polyether dilactams, Tetrahedron, 1999, 55(50):14467-14478
[56]庄俊鹏,杂芳基乙烯类化合物光化学性质及其相关配合物的研究,博士学位论文,天津大学, 2002年
[57]张运申,赵瑜藏,ε-溴代季膦盐的相转移Wittig反应研究,华夏医学, 2000年, 13(4): 446-448
[58]刘海军,杨金会, Wittig反应研究进展魏悌息反应,山西化工, 2006年26(5): 24-28
[59] Alfimov M. V., Gromov S. P., Fedorov Y. V. et al., Synthesis, structure, and ion selective complexation of trans and cis isomers of photochromic dithia-18-crown-6 ethers, J. Am. Chem. Soc., 1999, 121(21): 4992-5000
[60] Rurack K., Kollmannsberger M., Resch-Genger U., A selective and sensitive fluoroionoph- ore for HgII, AgI, and CuII with virtually decoupled fluorophore and receptor units, J. Am. Chem. Soc., 2000, 122(5): 968-969
[61] Krespan C. G.., Oxetane function spiro to polyoxaaza macroheterocycles, J. Org. Chem., 1975, 40(9): 1205-1209
[62] Hidefumi Sakamoto, Junichi Ishikawa and Makoto Otomo, Silver ion selective extraction with dithiaza-, tetrathiaza-, and tetrathiadiazacrown ether derivatives, Bull. Chem. Soc.Jpn., 1995, 68:2831-2836
[63] Brian D. P., William R. W., Susan M. P., Hypoxia-selective antitumor agents. 3. Relationships between structure and cytotoxicity against cultured tumor cells for substituted N,N-bis(2-chloroethyl)anilines, J. Med. Chem., 1990, 33(1): 112-121
[64] Tomoya Hirano, Kazuya Kikuchi and Yasuteru Urano, Novel zinc fluorescent probes excitable with visible light for biological applications, Angew. Chem., Int. Ed., 2000, 112(6): 1094-1096
[65] Zhang L. J., Lin H. K. and Bu X. H., Studies of the cation complexing ability of crowns Part ?. Synthesis, characterization and crystal structure of diazacrow -ns and their barium complexes, Inorg. Chim. Acta, 1995, 240: 257-262
[66] Mikio O., Yoshihisa I., Convenient and efficient tosylation of oligoethylene glycols and the related alcohols in tetrahydrofuran-water in the presence of sodium hydroxide, Bull. Chem. Soc.Jpn., 1990, 63(4): 1260-1262
[67] Sonveaux, E. The influence of side-chains on the complexation of cations by crowns, synthesis and cu(ii) complexation of n,n'-diaryl-diaza-18-crown-6, Tetrahedron, 1984, 40(4): 793-797
[68] SCHERING CORP, Monocyclic macrocyclic compounds and complexes thereof, US3966766, 1976-06-29
[69]张玲,焦天权,王彦博,对氯苯胺为端基的酰胺型开链冠醚的合成,兰州大学学报(自然科学版), 2002, 38(1): 72-75
[70] Dietrich B., Lehn J. M., Sauvage J. P., Cryptates -X: Syntheses et proprietes physiques de systemes diaza-polyoxa-macrobicycliques, Tetrahedron, 1973, 29(11): 1629-1645
[71] Johannes Kaulen and Hans J. Sch?fer, Oxidation of alcohols by electrochemicall- y regenerated nickel oxide hydroxide. Selective oxidation of hydroxysteroids, Tetrahedron, 1982, 38(22): 3299-3308
[72] Sonveaux E., The influence of side-chains on the complexation of cations by crowns., synthesis and cu(ii) complexation of n,n'-diaryl-diaza-18-crown-6, Tetrahedron, 1984,40(4): 793-797
[73] Herbert C. B., Peter H., Selective reductions. XVIII. Fast reaction of primary, secondary, and tertiary amides with diborane. Simple, convenient procedure for the conversion of amides to the corresponding amines, J. Org. Chem., 1973, 38(5): 912-916
[1] Bateman L., Olefin oxidation, Q. Rev. Chem. Soc., 1954, 8(2): 147-167
[2] Bolland J. L., Kinetics of olefin oxidation, Q. Rev. Chem. Soc., 1949, 3(1): 1-21
[3]崔洪光,受阻酚衍生物双酰肼(双酰胺)类抗氧剂合成新方法的研究,硕士学位论文,辽宁师范大学,2002年
[4]山西省化工研究所编,《塑料往胶加工助剂》,北京,化学工业出版社, 1983, 114
[5] James S. N., Qing Feng, Tjama Tjivikua et al., Kinetic studies and modeling of a self-replicating system, J. Am. Chem. Soc., 1991, 113(23): 8831-8839
[6] William S. K., Kuck J. A., and Robert C. E., Studies on lactones related to the cardiac aglycones VIIIβsubstituted-Δα,β-butenolides of the naphthalene and indene series, J. Org. Chem., 1942, 7(4): 374-382
[7] Takashi Tsujimoto, Hirishi Uyama and Shiro Kobayashi, Synthesis and curing behaviors of cross-linkable polynaphthols from renewable resources: preparation of artificial urushi, Macromolecules, 2004, 37(5): 1777-1782
[8] Chou W. C., Tan C. W. and Chen S. F., One-pot neat reactions of carboxylic esters and alkylenediamines for efficient preparation of N-acylalkylenediamines, J. Org. Chem., 1998, 63(26): 10015-10017
[9] Zhao H., Neamati N., Mazumder A. et al., Arylamide inhibitors of HIV-1 integrase, J. Med. Chem., 1997, 40(8): 1186-1194
[10] Zhang Z., Yin Z., Meanwell N. A. et al., Selective monoacylation of symmetrical diamines via prior complexation with boron, Org. Lett., 2003, 5(19): 3399-3402
[11] Abbott Lab, N-(2-benzimidazoly)-piperzines, US4093756, 1978-06-06
[12] Ramesh M. K., Joseph J. S. and Jack K., Synthesis and class III type antiarrhythmic activity of 4-aroyl (and aryl)-1-aralkylpiperazines, Bioorg. & Med. Chem. Lett., 2000, 10: 2819-2823
[13] Nicolaou K. C., Pfefferkorn J. A., Schuler F. et al., Combinatorial synthesis of novel and potent inhibitors of NADH: ubiquinone oxidoreductase, Chemistry & Biology, 2000, 7(12): 979-992
[2] Pedersen C. J., Crystalline salt complexes of macrocyclic polyethers, J. Am. Chem. Soc., 1970, 92(2): 386-391
[3] Dietrich B., Lehn J. M. and Sauvage J. P., Diaza-polyoxa-macrocycles et macrobic -ycles, Tetrahedron Lett., 10(34): 2885-2888
[4] Donald J. Cram, the Design of molecular hosts, guests, and their complexes, J. Angew. Chem., Int. Ed., 1988, 27(8): 1009-1020
[5] Bornet C., Amardeil R. and Meunier P., Structural and complexation properties of diselenacrown ethers. Synthesis and crystal structure of cationic palladium tetraselena complex, J.Chem. Soc., Dalton Trans., 1999, 7: 1039-1040
[6] Levason W., Quirk J. J., Selenoether Macrocyclic complexes of platinum(Ⅳ): synthesis and spectroscopic studies of [Pt([16]aneSe4)X2[PF6]2 (X=Cl, Br), X-ray structure of [Pt([16]aneSe4)Cl2[PF6]2, Inorg. Chem., 1994, 33(6): 6120-6122
[7]刘育,张衡益等,冠醚的分子设计及其识别性质研究进展,有机化学, 2002, 22 (2): 91-100
[8]胡旭波,钟振林,卢雪然等,杯环冠醚研究进展,化学通报, 1997, 4: 18-25
[9]高明章,杨奕群等,手性冠醚的研究进展,有机化学, 2001, 21(7): 477-484
[10]李卫平,刘秀芳,徐汉生等,硒杂冠醚的研究进展,化学通报, 1995, 7: 7-14
[11] Stock H. T., Kellogg R. M., Synthesis of enantiomerically pure thiocrown ethers derived from 1, 1'-binaphthalene-2, 2'-diol, J. Org. Chem., 1996, 61(9): 3093- 3105
[12]徐汉生,李卫平,刘秀芳等,碲杂冠醚及其铂配合物的合成,化学学报, 1994, 52(4): 386-390
[13] Atwood J. L., Dawies J. E. D., MacNicol D. D., Inclusion Compounds, New York, Acaedemic Press, 1984
[14] Szejtli J., Cyclodextrin and Their Inclusion Complexes, Budapest, Akademiai Kiado, 1982
[15] Patai S., Rappoport Z. Eds., Crown Ethers and Analogs, Chichester, John Wiley& Sons, 1989
[16] Pedersen C. J., Cyclic polyethers and their complexes with metal salts, J. Am. Chem. Soc., 1967, 89(26): 7017-7036
[17]刘育,尤长城,张衡益等,超分子化学-合成受体的分子识别与组装,天津,南开大学出版社, 2001年
[18] Pedersen C. J., Frenssdorff H K., Macrocyclic polyethers and their complexes, Angew. Chem. Int Ed., 1972, 11(1):16-25
[19] Dietrich B, Viout P, Lehn J-M., Macrocyclic chemistry-aspects of organic and inorganic supramolecular chemistry, New York, VCH, 1993
[20]韩建荣,张衡益和刘育,双臂式苯并-15-冠-5的合成及其对金属离子的选择键合,高等学校化学学报, 2005, 26(7): 1273-1276
[21] Pedersen C. J., Cyclic polyethers and their complexes with metal salts, J. Am. Chem. Soc., 1967, 89(10): 2495-2496
[22] Brown M. D., William L. and David C. M., Primary and secondary coordination of crown ethers to scandium(III). Synthesis, properties and structures of the reaction products of ScCl3(thf)3, ScCl3·6H2O and Sc(NO3)3·5H2O with crown ethers, J.Chem.Soc., Dalton Trans., 2003, 5: 857-865
[23]萨如拉,多酸-冠醚超分子配合物的合成及其性质研究,硕士学位论文,首都师范大学, 2006年
[24] Timko J. M., Moore s. s., Walba D.M. et al., Host-guest complexation. 2. Structural units that control association constants between polyethers and tert-butylammonium salts, J. Am. Chem. Soc., 1977, 99(13): 4207-4219
[25]张伯生,魏俊发等,光谱实验室,二苯并18-冠-6配合物[NH4(DB18-C-6)]2[Pd(SCN)4]的合成与结构分析, 2003, 4: 73-76
[26]董文魁,杨汝栋,稀土(Ш)(4',5'-二溴苯并-15-冠-5)配合物的制备及表征,兰州大学学报(自然科学版), 2000, 36(2): 48-53
[27]贺媛,魏俊发,窦建民等,光谱实验室, [Na(15-C-5)]2[Pd(SCN)4]配合物的合成与结构分析, 2003, 5: 86-88
[28]于洪利,张尊听,窦建民等,光谱实验室, Na(18-C-6)]2[Cu(i-mnt)2]的合成与结构分析, 2003, 4: 81-83
[29] Dou J. M., Gao X. K. and Dong F. Y., One- or two-dimensional 2,3-naphtho crown ether complexes [Na(N15C5)]2[M(SCN)4] and [K(N18C6)]2 [M(SCN)4] (M = Pd, Pt) constructed byπ-πstacking interactions, J. Chem. Soc., Dalton Trans., 2004, 18: 2918-2922
[30] Neier R. and Trojanowski C., Reduces polyoxomolybdates with the Keggin and Dawson structures: preparation and crystal structures of two-electron reduced [K(18-crown-6)]2[N(pph3)2]2[HPMo12O40] 8MeCN·18-crown-6 and four- electron reduced [NBun4]5-[H3S2Mo18O62]·4MeCN(18-crown-6=1,4,7,10, 13,16- hexaoxacyclooctade cane), J. Chem. Soc., Dalton Trans., 1995, 15: 2521-2533
[31] You W. S., Wang E. B. and Zhang H., Synthesis and structural characterization of a new supermolecular compound: H3PW12O40·6C14H20O5·16H2O (C14H20O5= benzo-15-crown-5), J. Mol. Struct., 2000, 554: 141-147
[32] W. S. You and E. B. Wang, Sythesis and crystal structure of a new supermolecular compound: [C12H24O6][H3PMo12O40]·22H2O(C12H24O6=18- crown-6), J. Mol. Struct., 2000, 524: 133-139
[33]鲁晓明,宗瑞发,刘顺成等,苯基氮杂-15-冠-5对钼同多酸以及钨钼杂多酸阴离子的选择,高等学校化学学报[J], 1997, 18(12): 1911-1916
[34] Tokuyama Soda Co., Schiff base-type benzocrown ether, JP60130584, 1985-07- 12
[35] Tokuyama Soda Co., Schiff base-type benzocrown ether, JP60130585, 1985-07- 12
[36] Yam V. W. W., Wong K. M. C. and Lee V. W.-M., Synthesis, photophysis, ion-binding, studies and structural characterization of organometallics rhenium(?) crown complexes, Organometallics, 1995, 14(9): 4034-4036
[37]张来新,杨琼,新取代冠醚及其缩氨硫脲和缩氨脲化合物的合成,新疆大学学报(自然科学版), 2001, 1: 70-73
[38]张来新,杨琼, 4′-甲酰缩氨(硫)脲苯并15冠5的合成,吉首大学学报(自然科学版), 2001, 3: 86-87
[39] Liu Y., Zhang H. Y., Bai X. P., Molecular design of crown ethers. 21. Synthesis of novel double-armed benzo-15-crown-5 lariats and their complexation thermo -dynamics with light lanthanoid nitrates in acetonitrile, J. Org. Chem., 2000, 65(21): 7105-7109
[40] Thomas W. B., George M. L. and Hideo N., Host-guest complexation. 25. Effects of substituents on the complexing properties of chorands, J. Org. Chem., 1983, 48(24): 4728-4734
[41] Green R. N., 18-crown-6: a strong complexing agent for alkali metal cations, Tetrahedron Lett., 1972, 13(18): 1793-1796
[42]吴成泰,鲁天保,中国化学会第一届应用化学学术讨论会,北京, 1985
[43] DU PONT, Macrocyclic heter imine complexing agents, US3847949, 1974-11- 12
[44] Pedersen C. J., Macrocyclic polyether sulfides, J. Org. Chem., 1971, 36(2), 254-257
[45]陈立钦,汪玉庭,黄载福,硫杂冠醚的合成,有机化学, 1990, 10(6): 546-549
[46]陈立钦,汪玉庭,黄载福,苯并硫冠醚的DSC研究,武汉化工学院学报, 1997, 19(4): 5-8
[47] Higuchi H., Tani K. and Otsubl T., New synthetic method of [2.2] cyclophanes via diselena [3.3] cyclophanes, Bull. Chem. Soc. Jpn., 1987, 60(11): 4027-4036
[48] Kumagai T., Preparation of novel selenacrown ethers and their complexing abililties with transition metal and heavy matal cations, Chem. lett., 1989, 213(9): 1667-1670
[49]徐汉生,李卫平,刘秀芳等,硒杂冠醚的合成及其络合性能研究,有机化学, 1993, 13(1): 52-57
[50] Hashem Sharghi, Khodabakhsh Niknam and Maryam Pooyan, The halogen–med -iated opening of epoxides in the presence of pyridine-containing macrocycles, Tetrahedron, 2001, 57(28): 6057-6064
[51] Pedersen C. J., Cyclic polyethers and their complexes with metal salts, J. Am. Chem. Soc., 1967, 89(26): 7017-7036
[52] Julia L. B., Anton K., Christian T. et al., On the development of sensor molecules that display FeШ-amplified fluorescence, J. Am. Chem. Soc., 2005, 127(39): 13522-13529
[53] Junichi Ishikama, Hidefumr Sakamoto and Tamao Mizuno, Hydrazones derived from dithiamonoaza and tetrathiamonoaza analogs of polyethers as silver ion selective ionophore: Syntheses, Proton-Dissociation fehaviors, and metal ion complexing properties in 1,4-dioxane-water acidic solution, Bull. Chem. Soc. Jpn., 1995, 68: 3071-3076
[54]徐强,宋仲容,陈凤鸣, 2,6-二甲酰基-4-甲基苯酚合成方法的改进,西南民族大学学报(自然科学版), 2005, 31(4): 525-526
[55] Shohreh Ghorbanian, Lina K. Mehta and John Parrick, Synthesis of some 24-membered tetralactam derivatives by an unexpectedly simple route, and some macrocyclic polyether dilactams, Tetrahedron, 1999, 55(50):14467-14478
[56]庄俊鹏,杂芳基乙烯类化合物光化学性质及其相关配合物的研究,博士学位论文,天津大学, 2002年
[57]张运申,赵瑜藏,ε-溴代季膦盐的相转移Wittig反应研究,华夏医学, 2000年, 13(4): 446-448
[58]刘海军,杨金会, Wittig反应研究进展魏悌息反应,山西化工, 2006年26(5): 24-28
[59] Alfimov M. V., Gromov S. P., Fedorov Y. V. et al., Synthesis, structure, and ion selective complexation of trans and cis isomers of photochromic dithia-18-crown-6 ethers, J. Am. Chem. Soc., 1999, 121(21): 4992-5000
[60] Rurack K., Kollmannsberger M., Resch-Genger U., A selective and sensitive fluoroionoph- ore for HgII, AgI, and CuII with virtually decoupled fluorophore and receptor units, J. Am. Chem. Soc., 2000, 122(5): 968-969
[61] Krespan C. G.., Oxetane function spiro to polyoxaaza macroheterocycles, J. Org. Chem., 1975, 40(9): 1205-1209
[62] Hidefumi Sakamoto, Junichi Ishikawa and Makoto Otomo, Silver ion selective extraction with dithiaza-, tetrathiaza-, and tetrathiadiazacrown ether derivatives, Bull. Chem. Soc.Jpn., 1995, 68:2831-2836
[63] Brian D. P., William R. W., Susan M. P., Hypoxia-selective antitumor agents. 3. Relationships between structure and cytotoxicity against cultured tumor cells for substituted N,N-bis(2-chloroethyl)anilines, J. Med. Chem., 1990, 33(1): 112-121
[64] Tomoya Hirano, Kazuya Kikuchi and Yasuteru Urano, Novel zinc fluorescent probes excitable with visible light for biological applications, Angew. Chem., Int. Ed., 2000, 112(6): 1094-1096
[65] Zhang L. J., Lin H. K. and Bu X. H., Studies of the cation complexing ability of crowns Part ?. Synthesis, characterization and crystal structure of diazacrow -ns and their barium complexes, Inorg. Chim. Acta, 1995, 240: 257-262
[66] Mikio O., Yoshihisa I., Convenient and efficient tosylation of oligoethylene glycols and the related alcohols in tetrahydrofuran-water in the presence of sodium hydroxide, Bull. Chem. Soc.Jpn., 1990, 63(4): 1260-1262
[67] Sonveaux, E. The influence of side-chains on the complexation of cations by crowns, synthesis and cu(ii) complexation of n,n'-diaryl-diaza-18-crown-6, Tetrahedron, 1984, 40(4): 793-797
[68] SCHERING CORP, Monocyclic macrocyclic compounds and complexes thereof, US3966766, 1976-06-29
[69]张玲,焦天权,王彦博,对氯苯胺为端基的酰胺型开链冠醚的合成,兰州大学学报(自然科学版), 2002, 38(1): 72-75
[70] Dietrich B., Lehn J. M., Sauvage J. P., Cryptates -X: Syntheses et proprietes physiques de systemes diaza-polyoxa-macrobicycliques, Tetrahedron, 1973, 29(11): 1629-1645
[71] Johannes Kaulen and Hans J. Sch?fer, Oxidation of alcohols by electrochemicall- y regenerated nickel oxide hydroxide. Selective oxidation of hydroxysteroids, Tetrahedron, 1982, 38(22): 3299-3308
[72] Sonveaux E., The influence of side-chains on the complexation of cations by crowns., synthesis and cu(ii) complexation of n,n'-diaryl-diaza-18-crown-6, Tetrahedron, 1984,40(4): 793-797
[73] Herbert C. B., Peter H., Selective reductions. XVIII. Fast reaction of primary, secondary, and tertiary amides with diborane. Simple, convenient procedure for the conversion of amides to the corresponding amines, J. Org. Chem., 1973, 38(5): 912-916
[1] Bateman L., Olefin oxidation, Q. Rev. Chem. Soc., 1954, 8(2): 147-167
[2] Bolland J. L., Kinetics of olefin oxidation, Q. Rev. Chem. Soc., 1949, 3(1): 1-21
[3]崔洪光,受阻酚衍生物双酰肼(双酰胺)类抗氧剂合成新方法的研究,硕士学位论文,辽宁师范大学,2002年
[4]山西省化工研究所编,《塑料往胶加工助剂》,北京,化学工业出版社, 1983, 114
[5] James S. N., Qing Feng, Tjama Tjivikua et al., Kinetic studies and modeling of a self-replicating system, J. Am. Chem. Soc., 1991, 113(23): 8831-8839
[6] William S. K., Kuck J. A., and Robert C. E., Studies on lactones related to the cardiac aglycones VIIIβsubstituted-Δα,β-butenolides of the naphthalene and indene series, J. Org. Chem., 1942, 7(4): 374-382
[7] Takashi Tsujimoto, Hirishi Uyama and Shiro Kobayashi, Synthesis and curing behaviors of cross-linkable polynaphthols from renewable resources: preparation of artificial urushi, Macromolecules, 2004, 37(5): 1777-1782
[8] Chou W. C., Tan C. W. and Chen S. F., One-pot neat reactions of carboxylic esters and alkylenediamines for efficient preparation of N-acylalkylenediamines, J. Org. Chem., 1998, 63(26): 10015-10017
[9] Zhao H., Neamati N., Mazumder A. et al., Arylamide inhibitors of HIV-1 integrase, J. Med. Chem., 1997, 40(8): 1186-1194
[10] Zhang Z., Yin Z., Meanwell N. A. et al., Selective monoacylation of symmetrical diamines via prior complexation with boron, Org. Lett., 2003, 5(19): 3399-3402
[11] Abbott Lab, N-(2-benzimidazoly)-piperzines, US4093756, 1978-06-06
[12] Ramesh M. K., Joseph J. S. and Jack K., Synthesis and class III type antiarrhythmic activity of 4-aroyl (and aryl)-1-aralkylpiperazines, Bioorg. & Med. Chem. Lett., 2000, 10: 2819-2823
[13] Nicolaou K. C., Pfefferkorn J. A., Schuler F. et al., Combinatorial synthesis of novel and potent inhibitors of NADH: ubiquinone oxidoreductase, Chemistry & Biology, 2000, 7(12): 979-992
© 2004-2018 中国地质图书馆版权所有 京ICP备05064691号 京公网安备11010802017129号 地址：北京市海淀区学院路29号 邮编：100083 电话：办公室：(+86 10)66554848；文献借阅、咨询服务、科技查新：66554700 |