Prins反应的研究和应用现状
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摘要
结合Prins反应的发展历史,概述了近年来Prins反应的最新研究及应用现状。目前Prins反应有直接热缩合反应和催化合成反应两大类,本文分析了这两大类反应的优势和不足,指出了未来催化合成反应是Prins反应研究的重点。Prins反应的催化剂包括液体酸催化剂、固体酸催化剂和固体碱催化剂等,而离子液体催化剂、杂多酸催化剂、竹炭磺酸催化剂等高效且环境友好型催化剂是今后研究发展的重点。同时概述了Prins反应在化工、农药、香料、医药、天然大分子合成等方面的应用,最后提出了Prins反应未来在新型催化剂、相关合成方法学、石油化工和天然产物全合成等相关领域发展方向的展望。
According to the development history of Prins reaction,the present research and application situation of Prins reaction were summarized in this paper.At present,the Prins reaction takes place through direct thermal condensation way without catalysts or catalytic synthesis reaction.The advantage and disadvantage of these two kinds of reaction were analyzed.We find the catalytic synthesis reaction was the topic of the research in the future.The catalysts of Prins reaction include liquid acid catalysts,solid acid catalysts,solid base catalysts.The development of high efficient and environment friendly catalysts,such as ionic liquid catalysts,heteropoly acid catalysts and the bamboo charcoal catalysts,were the topic of the research in the future.The applications of the Prins reaction in the field of chemical industry,pesticides,spice and natural polymer synthesis were reported in this paper.Finally,the development of Prins reaction in novel catalysts,relevant synthetic methodologies,petrochemical industry and synthesis of natural products were briefly reviewed in this paper.
According to the development history of Prins reaction,the present research and application situation of Prins reaction were summarized in this paper.At present,the Prins reaction takes place through direct thermal condensation way without catalysts or catalytic synthesis reaction.The advantage and disadvantage of these two kinds of reaction were analyzed.We find the catalytic synthesis reaction was the topic of the research in the future.The catalysts of Prins reaction include liquid acid catalysts,solid acid catalysts,solid base catalysts.The development of high efficient and environment friendly catalysts,such as ionic liquid catalysts,heteropoly acid catalysts and the bamboo charcoal catalysts,were the topic of the research in the future.The applications of the Prins reaction in the field of chemical industry,pesticides,spice and natural polymer synthesis were reported in this paper.Finally,the development of Prins reaction in novel catalysts,relevant synthetic methodologies,petrochemical industry and synthesis of natural products were briefly reviewed in this paper.
引文
[1]ADAMS D R,BHATNAGAR S P.The Prins reaction[J].Synthesis,1977,1977(10):661-672.
[2]JIANG P,LI F,XU Y,et al.Palladium-catalyzed C—H arylation[J].Synfacts,2016,23:187.
[3]杨艺.五元、六元含氧杂环的成环反应研究[D].兰州:兰州大学,2011.
[4]PRICE C C,BENTON F L,SCHMIDLE C J.The preparation of some 2-aryl-1,3-butadienes[J].J.Am.Chem.Soc,2002,28:707-727.
[5]RISI C D,FANTON G,POLLINI G P,et al.Recent advances in the stereoselective synthesis of trans-3,4-disubstitutedpiperidines:applications to(-)-paroxetine[J].Tetrahedron Asymmetry,2008,19:131-155.
[6]HANSCHKE Ernst.Zur kenntnis der prinsschen reaktion,I.mitteil.:über die umsetzung von butadien mit formaldehyd[J].Berichte Der Deutschen Chemischen Gesellschaft,1955,88:1043-1048.
[7]YANG N C,YANG D D H,ROSS C B.The mechanism of the Prins reaction1[J].Journal of the American Chemical Society,1959,81(1):133-136.
[8]刘季铨,李连地,闻霞,等.甲醛异丁烯热缩合合成3-甲基-3-丁烯-1-醇[J].精细化工,2011,28(3):293-295.
[9]STAPP P R.The condensation of.α-olefins with paraformaldehyde,acetylating agents,and hydrogen chloride[J].J.Org.Chem,1971,36(17):2505-2507.
[10]STAPP P R,RANDALL J C.Condensation of cyclic olefins with paraformaldehyde and hydrogen chloride[J].Journal of Organic Chemistry,2002,35:2948-2955.
[11]BLOMQUIST A T,VERDOL J A.The thermal isobutyleneformaldehyde condensation[J].Journal of the American Chemical Society,1955,77:78-80.
[12]WILHELM F.Cyclic acetals of formaldehyde and a process of preparing them:US2325760[P].1943-08-03.
[13]LASZLO C,ANDRAS N,FERENC S,et al.A convenient synthesis of(-)-paroxetine[J].European Journal of Organic Chemistry,2004,2004:3336-3339.
[14]SHARF V Z,FREIDLIN L K,OPARINA G K,et al.Production of isoprene from formaldehyde and isobutylene through 3-methylbutanediol-1,3[J].Bulletin of the Academy of Sciences of the Ussr Division of Chemical Science,1965,14:1621-1623.
[15]王雯娟.新型功能化离子液体的合成及其酸催化有机反应性能的研究[D].上海:华东师范大学,2008.
[16]雷敏,赵应伟,吴丽,等.酸功能化离子液体催化三聚甲醛与烯烃的Prins反应[J].分子催化,2013,27(2):107-114.
[17]YADAV J S,REDDY B S,REDDY M S,et al.Lewis acidic chloroaluminate ionic liquids:novel reaction media for the synthesis of 4-chloropyrans[J].European Journal of Organic Chemistry,2003,2003(9):1779-1783.
[18]宋河远,唐中华,陈静.功能化酸性离子液体催化甲醛与烯烃的Prins缩合反应[J].分子催化,2008,22(5):403-407.
[19]DOSKOCIL E J,YALURIS G,CORMA A,et al.Modified zeolite catalyst:EP2269734[P].2011-05-01.
[20]DUMITRIU E,ON D T,KALIAGUINE S.Isoprene by Prins condensation over acidic molecular sieves[J].Journal of Catalysis,1997,170:150-160.
[21]黄永生,冯海波.催化Prins成环反应的研究综述[J].舰船防化,2009(3):12-14.
[22]LI Guixian,G U Yanlong,DING Yong,et al.Wells-Dawson type molybdovanadophosphoric heteropolyacids catalyzed Prins cyclization of alkenes with paraformaldehyde under mild conditions-a facile and efficient method to 1,3-dioxane derivatives[J].Journal of Molecular Catalysis A Chemical,2004,218:147-152.
[23]吴庆银,林桐枫.钨锗酸催化苯乙烯与福尔马林的Prins反应研究[J].当代化工,1996(3):2-3.
[24]商红岩,郭振国,徐成娟,等.甲醛和异戊烯普林斯(Prins)缩合反应的动力学研究[J].石油化工高等学校学报,2013(5):27-32.
[25]彭佳梦,阳志高,尹笃林.竹炭磺酸催化普林斯反应的研究[J].广州化学,2015,40(2):27-31.
[26]HATTORI H.ChemInform abstract:heterogeneous basic catalysis[J].ChemInform,1995,26:537-558.
[27]BOUMAZA A,FAVARO L,LDION J,et al.Transition alumina phases induced by heat treatment of boehmite:an Xray diffraction and infrared spectroscopy study[J].Journal of Solid State Chemistry,2009,182:1171-1176.
[28]耿艳霞,俞丹群,刘纯山.普林斯(Prins)缩合反应一步制备3-甲基-3-丁烯-1-醇[J].工业催化,2005,12(s1):346-348.
[29]YOSHIDA Y,YAMAMOTO Y.Process for preparing unsaturated alcohols:US4028424[P].1977-06-07.
[30]WANG X,WANG T,HUA W,et al.Synthesis of zirconia porous phosphate heterostructures(Zr-PPH)for Prins condensation[J].Catalysis Communications,2014,43:97-101.
[31]王海永,吕慧,林晨,等.碱性载体对负载型CoO催化剂催化性能的影响[J].化工学报,2015,66(10):3911-3918.
[32]刘俊涛,孙凤侠,滕加伟.碳四烯烃催化裂解制乙烯和丙烯热力学分析及反应性能考察[J].工业催化,2015(6):486-490.
[33]周哲,刘清,费兆阳,等.催化合成3-甲基-3-丁烯-1-醇醋酸酯及其水解过程研究[J].化学工程,2014,42(1):55-59.
[34]刘海超,刘季铨,郭启文,等.固载化ZnCl2催化合成3-甲基-3-丁烯-1-醇[J].燃料化学学报,2013,41(9):1146-1152.
[35]王建芬,丁双阳,王晓琳.含氟杀虫剂类农药的残留检测分析研究进展[J].中国农学通报,2016(2):68-72.
[36]汪乐丰.DV-菊酸合成方法[J].精细化工中间体,1994(3):23-26.
[37]汪昭玮,于俊伟,刘晓暄.钛系催化剂合成聚异戊二烯橡胶的研究进展[J].化工进展,2014,33(11):2941-2946.
[38]姚臻,张景,屠宇侠,等.高顺式聚异戊二烯橡胶的研究进展[J].化工进展,2015,34(1):160-165.
[39]贾小永.固体酸催化异丁烯和甲醛合成异戊二烯的研究[D].长沙:湖南大学,2013.
[40]王占军,武法文,王志祥,等.异长叶烯酮合成条件优化及动力学[J].化工进展,2015,34(3):815-819.
[41]余德润,黄晓宾,李冲,等.异长叶烯Prins反应及其产物的分离[J].江西师范大学学报(自然科学版),2005,29(6):522-524.
[42]王植材,邓逊知.长叶烯通过异构化氧化和Prins反应合成新型香料[J].化学研究与应用,1996,8(3):364-368.
[43]温梅姣,常卫星,李靖.四氯化锡诱导的Prins环化法高选择性地合成四氢吡喃衍生物[J].高等学校化学学报,2005,3:452-455.
[44]COHEN F,MACMILLAN D W C,OVERMAN L E,et al.Stereoselection in the Prins-pinacol synthesis of acyltetrahydrofurans[J].Organic Letters,2001,3:1225-1228.
[45]窦飞.区域选择性地构筑含氧及含氮杂环[D].徐州:江苏师范大学,2014.
[46]REDDY B V S,MEDABOINA D,SRIDHAR B,et al.Stereoselective synthesis of hexahydro-1H-pyrano-and thiopyrano[3,4-c]quinoline derivatives through a Prins cascade cyclization[J].Journal of Organic Chemistry,2013,78:8161-8168.
[47]SCHULTE-ELTE K H,HAUSER A,OHLOFF G.Macrocyclic ring closure of OH-assisted Prins reaction.A new and efficient synthesis of(R,S)-muscone[J].Helvetica Chimica Acta,1979,62:2673-2680.
[48]BAHNCK K B,RYCHNOVSKY S D.Formal synthesis of(-)-kendomycin featuring a Prins-cyclization to construct the macrocycle[J].Journal of the American Chemical Society,2008,130:13177-13181.
[49]SU Q,DAKIN L A,PANEK J S.[4+2]-Annulations of chiral organosilanes:application to the total synthesis of leucascandrolide A[J].Journal of Organic Chemistry,2007,72:2-24.
[50]GHOSH A K,CHENG X,BAI R,et al.Total synthesis of potent antitumor macrolide(-)-zampanolide:an oxidative intramolecular cyclization-based strategy[J].European Journal of Organic Chemistry,2012,2012:4130-4139.
[2]JIANG P,LI F,XU Y,et al.Palladium-catalyzed C—H arylation[J].Synfacts,2016,23:187.
[3]杨艺.五元、六元含氧杂环的成环反应研究[D].兰州:兰州大学,2011.
[4]PRICE C C,BENTON F L,SCHMIDLE C J.The preparation of some 2-aryl-1,3-butadienes[J].J.Am.Chem.Soc,2002,28:707-727.
[5]RISI C D,FANTON G,POLLINI G P,et al.Recent advances in the stereoselective synthesis of trans-3,4-disubstitutedpiperidines:applications to(-)-paroxetine[J].Tetrahedron Asymmetry,2008,19:131-155.
[6]HANSCHKE Ernst.Zur kenntnis der prinsschen reaktion,I.mitteil.:über die umsetzung von butadien mit formaldehyd[J].Berichte Der Deutschen Chemischen Gesellschaft,1955,88:1043-1048.
[7]YANG N C,YANG D D H,ROSS C B.The mechanism of the Prins reaction1[J].Journal of the American Chemical Society,1959,81(1):133-136.
[8]刘季铨,李连地,闻霞,等.甲醛异丁烯热缩合合成3-甲基-3-丁烯-1-醇[J].精细化工,2011,28(3):293-295.
[9]STAPP P R.The condensation of.α-olefins with paraformaldehyde,acetylating agents,and hydrogen chloride[J].J.Org.Chem,1971,36(17):2505-2507.
[10]STAPP P R,RANDALL J C.Condensation of cyclic olefins with paraformaldehyde and hydrogen chloride[J].Journal of Organic Chemistry,2002,35:2948-2955.
[11]BLOMQUIST A T,VERDOL J A.The thermal isobutyleneformaldehyde condensation[J].Journal of the American Chemical Society,1955,77:78-80.
[12]WILHELM F.Cyclic acetals of formaldehyde and a process of preparing them:US2325760[P].1943-08-03.
[13]LASZLO C,ANDRAS N,FERENC S,et al.A convenient synthesis of(-)-paroxetine[J].European Journal of Organic Chemistry,2004,2004:3336-3339.
[14]SHARF V Z,FREIDLIN L K,OPARINA G K,et al.Production of isoprene from formaldehyde and isobutylene through 3-methylbutanediol-1,3[J].Bulletin of the Academy of Sciences of the Ussr Division of Chemical Science,1965,14:1621-1623.
[15]王雯娟.新型功能化离子液体的合成及其酸催化有机反应性能的研究[D].上海:华东师范大学,2008.
[16]雷敏,赵应伟,吴丽,等.酸功能化离子液体催化三聚甲醛与烯烃的Prins反应[J].分子催化,2013,27(2):107-114.
[17]YADAV J S,REDDY B S,REDDY M S,et al.Lewis acidic chloroaluminate ionic liquids:novel reaction media for the synthesis of 4-chloropyrans[J].European Journal of Organic Chemistry,2003,2003(9):1779-1783.
[18]宋河远,唐中华,陈静.功能化酸性离子液体催化甲醛与烯烃的Prins缩合反应[J].分子催化,2008,22(5):403-407.
[19]DOSKOCIL E J,YALURIS G,CORMA A,et al.Modified zeolite catalyst:EP2269734[P].2011-05-01.
[20]DUMITRIU E,ON D T,KALIAGUINE S.Isoprene by Prins condensation over acidic molecular sieves[J].Journal of Catalysis,1997,170:150-160.
[21]黄永生,冯海波.催化Prins成环反应的研究综述[J].舰船防化,2009(3):12-14.
[22]LI Guixian,G U Yanlong,DING Yong,et al.Wells-Dawson type molybdovanadophosphoric heteropolyacids catalyzed Prins cyclization of alkenes with paraformaldehyde under mild conditions-a facile and efficient method to 1,3-dioxane derivatives[J].Journal of Molecular Catalysis A Chemical,2004,218:147-152.
[23]吴庆银,林桐枫.钨锗酸催化苯乙烯与福尔马林的Prins反应研究[J].当代化工,1996(3):2-3.
[24]商红岩,郭振国,徐成娟,等.甲醛和异戊烯普林斯(Prins)缩合反应的动力学研究[J].石油化工高等学校学报,2013(5):27-32.
[25]彭佳梦,阳志高,尹笃林.竹炭磺酸催化普林斯反应的研究[J].广州化学,2015,40(2):27-31.
[26]HATTORI H.ChemInform abstract:heterogeneous basic catalysis[J].ChemInform,1995,26:537-558.
[27]BOUMAZA A,FAVARO L,LDION J,et al.Transition alumina phases induced by heat treatment of boehmite:an Xray diffraction and infrared spectroscopy study[J].Journal of Solid State Chemistry,2009,182:1171-1176.
[28]耿艳霞,俞丹群,刘纯山.普林斯(Prins)缩合反应一步制备3-甲基-3-丁烯-1-醇[J].工业催化,2005,12(s1):346-348.
[29]YOSHIDA Y,YAMAMOTO Y.Process for preparing unsaturated alcohols:US4028424[P].1977-06-07.
[30]WANG X,WANG T,HUA W,et al.Synthesis of zirconia porous phosphate heterostructures(Zr-PPH)for Prins condensation[J].Catalysis Communications,2014,43:97-101.
[31]王海永,吕慧,林晨,等.碱性载体对负载型CoO催化剂催化性能的影响[J].化工学报,2015,66(10):3911-3918.
[32]刘俊涛,孙凤侠,滕加伟.碳四烯烃催化裂解制乙烯和丙烯热力学分析及反应性能考察[J].工业催化,2015(6):486-490.
[33]周哲,刘清,费兆阳,等.催化合成3-甲基-3-丁烯-1-醇醋酸酯及其水解过程研究[J].化学工程,2014,42(1):55-59.
[34]刘海超,刘季铨,郭启文,等.固载化ZnCl2催化合成3-甲基-3-丁烯-1-醇[J].燃料化学学报,2013,41(9):1146-1152.
[35]王建芬,丁双阳,王晓琳.含氟杀虫剂类农药的残留检测分析研究进展[J].中国农学通报,2016(2):68-72.
[36]汪乐丰.DV-菊酸合成方法[J].精细化工中间体,1994(3):23-26.
[37]汪昭玮,于俊伟,刘晓暄.钛系催化剂合成聚异戊二烯橡胶的研究进展[J].化工进展,2014,33(11):2941-2946.
[38]姚臻,张景,屠宇侠,等.高顺式聚异戊二烯橡胶的研究进展[J].化工进展,2015,34(1):160-165.
[39]贾小永.固体酸催化异丁烯和甲醛合成异戊二烯的研究[D].长沙:湖南大学,2013.
[40]王占军,武法文,王志祥,等.异长叶烯酮合成条件优化及动力学[J].化工进展,2015,34(3):815-819.
[41]余德润,黄晓宾,李冲,等.异长叶烯Prins反应及其产物的分离[J].江西师范大学学报(自然科学版),2005,29(6):522-524.
[42]王植材,邓逊知.长叶烯通过异构化氧化和Prins反应合成新型香料[J].化学研究与应用,1996,8(3):364-368.
[43]温梅姣,常卫星,李靖.四氯化锡诱导的Prins环化法高选择性地合成四氢吡喃衍生物[J].高等学校化学学报,2005,3:452-455.
[44]COHEN F,MACMILLAN D W C,OVERMAN L E,et al.Stereoselection in the Prins-pinacol synthesis of acyltetrahydrofurans[J].Organic Letters,2001,3:1225-1228.
[45]窦飞.区域选择性地构筑含氧及含氮杂环[D].徐州:江苏师范大学,2014.
[46]REDDY B V S,MEDABOINA D,SRIDHAR B,et al.Stereoselective synthesis of hexahydro-1H-pyrano-and thiopyrano[3,4-c]quinoline derivatives through a Prins cascade cyclization[J].Journal of Organic Chemistry,2013,78:8161-8168.
[47]SCHULTE-ELTE K H,HAUSER A,OHLOFF G.Macrocyclic ring closure of OH-assisted Prins reaction.A new and efficient synthesis of(R,S)-muscone[J].Helvetica Chimica Acta,1979,62:2673-2680.
[48]BAHNCK K B,RYCHNOVSKY S D.Formal synthesis of(-)-kendomycin featuring a Prins-cyclization to construct the macrocycle[J].Journal of the American Chemical Society,2008,130:13177-13181.
[49]SU Q,DAKIN L A,PANEK J S.[4+2]-Annulations of chiral organosilanes:application to the total synthesis of leucascandrolide A[J].Journal of Organic Chemistry,2007,72:2-24.
[50]GHOSH A K,CHENG X,BAI R,et al.Total synthesis of potent antitumor macrolide(-)-zampanolide:an oxidative intramolecular cyclization-based strategy[J].European Journal of Organic Chemistry,2012,2012:4130-4139.