2-烷基-2-(芳磺酰基)乙酸酯的高效共轭加成  

A Facile and Efficient Conjugate Addition of 2-Alkyl-2-(arylsulfonyl) acetates to the α,β-Unsaturated Compounds

作　　者：刘广鉴 张正[1] 王玉良 孙于萍 柏亚罗 

机构地区：[1]南京大学化学系,江苏南京210093

出　　处：《有机化学》1995年第6期590-594,共5页Chinese Journal of Organic Chemistry

摘　　要：本文报道在固-液相转移催化的温和条件下2-烷基-2-(芳磺酰基)乙酸酯(1)与x,β-不饱和酯、腈、酮(2)的高选择性和高效率共轭加成反应,成功地合成了2,2-二取代戊二酸二酯(3a～d)、4-氰基丁酸酯(3e～g)和5-氧代己酸酯(3h～j),对它们的结构作了表征,初步讨论了本合成法的特点、Michael受体、相转移催化剂和溶剂等对共轭加成反应的影响。1,5-Difunctional compounds are of great importance in both of fine chemical industry and organic synthesis; many of them are useful building blocks for the construction of more complex molecules, and some of them have antimicrobial, virucidal or anticancer activities. This paper reports a facile and efficient synthesis of the 2,2-disubstituted new 1.5-difunctional compounds (3a- j) via the conjugate addition of 2-alkyl-2-(arylsulfonyl) acetates (1) to the α,β-unsa-turated esters, nitrile. and ketone (2). The reaction proceeded very smoothly and selectively under solid-liquid PTC conditions to give the 2-alkyl-2-(arylsulfonyl) pentanedioic acid diesters (3a-d) . 2-alkyl-2-(arylsulfonyl)-4-cyanobutanoates (3e- g). and 2-alkyl-2-(arylsulfonyl)-5-oxohexanoates (3h-j) in good to excellent yields. All new compounds (3a- j) have been fully characterized by IR, 1H NMR, MS. and elemental analyses. Some major advantages of the method, effects of the Michael acceptors (2), phase-transfer catalyst and solvents on the conjugate addition are also discussed briefly.

关 键 词：烷基 芳磺酰基 乙酸酯 共轭加成 

分 类 号：O623.624.1[理学—有机化学]