有机化学 ›› 1995, Vol. 15 ›› Issue (6): 590-594. 上一篇    下一篇

研究论文

2-烷基-2-(芳磺酰基)乙酸酯的高效共轭加成

刘广鉴;张正;王玉良;孙于萍;柏亚罗   

  1. 南京大学化学系
  • 发布日期:1995-12-25

A facile and efficient conjugate addition of 2-alkyl-2- (arylsulfonyl) acetates to the α, β-unsaturated compounds

LIU GUANGJIAN;ZHANG ZHENG;WANG YULIANG;SUN YUPING;BAI YALUO   

  • Published:1995-12-25

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α, 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。

关键词: 丁酸酯, 腈, 酯, 己酸酯, 元素分析, 乙酸酯 P, 共轭加成, 酮, 核磁共振谱法, 相转移催化

1, 5-Difunctional compounds are of great importance in both of fine chemical indus-try 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 com-pounds (3a~j) via the conjugate addition of 2-alkyl-2-(arylsulfonyl) acetates (1) to the α, β-unsaturated 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 analysis. Some major advantages of te method, ef-fects of the Michael acceptors (2), phase-transfer catalyst and solvents on the conjugate addition are also discussed briefly.

Key words: ESTERS, BUTYRIC ESTER, ELEMENTAL ANALYSIS, NITRILE, NMR SPECTROMETRY, KETONE, ACETIC ACID ESTER P, PHASE TRANSFER CATALYSIS

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