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现代化工  2017, Vol. 37 Issue (12): 153-157    DOI: 10.16606/j.cnki.issn0253-4320.2017.12.036
  科研与开发 本期目录 | 过刊浏览 | 高级检索 |
新型硫脲类小分子催化剂的合成与应用
马淑敏, 张晶, 陈立功, 闫喜龙, 李阳
天津大学化工学院, 天津 300350
Synthesis and application of novel thiourea based small molecule catalysts
MA Shu-min, ZHANG Jing, CHEN Li-gong, YAN Xi-long, LI Yang
School of Chemical Engineering and Technology, Tianjin University, Tianjin 300350, China
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摘要 设计合成了一类多氢键供体的硫脲类小分子催化剂。该催化剂对丙二腈与硝基苯乙烯的不对称Michael加成反应具有一定的催化性能,收率可达79%,ee值为11%。该催化剂在催化不对称Michael加成反应时表现出酶催化的特性,对反应底物具有一定的专一性,且催化剂中手性中心构型一致时才具有催化性能。
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马淑敏
张晶
陈立功
闫喜龙
李阳
关键词:  硫脲类小分子催化剂  不对称Michael加成反应  丙二腈    
Abstract: A new series of thiourea based small molecular catalysts with multi hydrogen donor is designed and synthesized.These catalysts can be used in the asymmetric Michael addition reaction between malononitrile and nitro styrene,leading to a yield of 79% and an ee value of 11%.The catalysts show a similarity to the specificity of enzyme catalysis in catalyzing asymmetric Michael addition reaction,and only the catalysts that have consistent structure in multi chiral centers show catalytic property.
Key words:  thiourea based small molecular catalyst    asymmetric Michael addition reaction    malononitrile
收稿日期:  2017-06-08                出版日期:  2017-12-20
TQ031.2  
  TQ032.42  
通讯作者:  李阳(1971-),男,博士,副教授,主要从事精细化工研究,通讯联系人,liyang777@tju.edu.cn。    E-mail:  liyang777@tju.edu.cn
作者简介:  马淑敏(1989-),女,硕士研究生,研究方向为手性小分子催化剂,msn815@163.com
引用本文:    
马淑敏, 张晶, 陈立功, 闫喜龙, 李阳. 新型硫脲类小分子催化剂的合成与应用[J]. 现代化工, 2017, 37(12): 153-157.
MA Shu-min, ZHANG Jing, CHEN Li-gong, YAN Xi-long, LI Yang. Synthesis and application of novel thiourea based small molecule catalysts. Modern Chemical Industry, 2017, 37(12): 153-157.
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http://www.xdhg.com.cn/CN/10.16606/j.cnki.issn0253-4320.2017.12.036  或          http://www.xdhg.com.cn/CN/Y2017/V37/I12/153
[1] 邢其毅.基础有机化学[M].北京:高等教育出版社,2013:100-126.
[2] 胡文浩,周静.手性,手性药物及手性合成[J].专论——化学前沿,2009,5:1-3.
[3] 张芳,张霞,刘春美,等.生物催化及其在手性技术中的应用[J].现代化工,2011,31(12):7-11.
[4] Sigman M S,acobsen E N J.Schiff base catalysts for the asymmetric Strecker reaction identified and optimized from parallel synthetic libraries[J].Journal of the American Chemical Society,1998,120(19):4901-4902.
[5] Zhou Wenming,Liu Han,Du Daming.Organocatalytic highly enantioselectiveMic-hael addition of 2-hydroxy-1,4-naphthoquin-ones to nitroalkenens[J].Organic Letters,2008,10(13):2817-2820.
[6] Huang H B,Jacobsen E N.Highly enantioselective direct conjugate addition of ketones to nitroalkenes promoted by achiral primary amine-thiourea catalyst[J].Journal of the American Chemical Society,2006,128(22):7170-7171.
[7] Christoforos G Kokotos,George Kokotos.Primary amine-thioureas based on tert-butyl esters of natural amino acids as organo-catalysts for the Michael reaction[J].Adv Synth Catal,2009,351:1355-1362.
[8] Seamus H McCooey,Stephen J Connon.Urea-and thiourea-substituted cinchona alk-aloidderivatives as highly efficient bifunc-tionalorganocatalystsfor the asymmetric addition of malonate to nitroalkenes:Inver-sion of configuration at C9 dramatically improves catalyst performance[J].Angew Chem,2005,117:6525-6528.
[9] Ye J X,Darren J Dixon,Peter S Hynes.Enantioselective organocatalytic Michael addition of malonates to nitro olefins using bifunctional cinchonine derivatives[J].Chem Commun,2005,4481-4483.
[10] Cao C L,Ye M C,Tang Y,et al.Pyrrolidine-thiourea as bifunctional organo-catalyst:Highly enantioselective Michael addition of cyclohexanone to nitroolefins[J].Organic Letters,2006,8(14):2901-2904.
[11] Cao Y J,Lai Y Y,Xiao W J,et al.Michael additions in water of ketones to nitroolefins catalyzed by readily tunable and bifunctional pyrrolidine-thiourea organo-catalysts[J].Tetrahedron Letters,2007,48(1):21-24.
[12] Deng F,Liu H Y.Novelbifunctionalorganocatalyst using sulfamide as hydrogen bonding donor:Application in asymmetric Michael addition of cyclic ketones to nitro-olefins[J].Synthetic Communications,2012,42:767-774.
[13] Okino T,Hoashi Y,Takemoto Y.Enantioselective Michael reaction of malonates to nitroolefins catalyzed by bifunctionalorganocatalysts[J].Journal of the American Chemical Society,2003,125(42):12672-12673.
[14] Wang C J,Zhang Z H,Dong X Q,et al.Hydrogen bonding donors:Highly efficient organocatalysts for asymmetric Michael addition of acetylacetone to nitroolefins[J].Chemical Communication,2008:1431-1433.
[15] Jin H,Cho S M,Ryu D H,et al.Role of configuration at C6 in catalytic activity of L-proline-derived functional organo-catalysts[J].Organic Letters,2017,19:2434-2437.
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[6] . [J]. , 2010, 30(3): 0 .
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