高等学校化学学报

高等学校化学学报 ›› 1993, Vol. 14 ›› Issue (5): 638.

• 研究论文 • 上一篇    下一篇

含硫碳负离子的反应和应用研究(Ⅶ)——4,4-二取代1,7-二官能团化合物的合成

刘广鉴, 张正, 王玉良, 周卫清, 张立康, 柏亚罗   

  1. 南京大学化学系, 南京 210008
  • 收稿日期:1992-05-17 修回日期:1992-12-26 出版日期:1993-05-24 发布日期:1993-05-24
  • 通讯作者: 刘广鉴

Studies on Reactions of Sulfur-containing Carbanions and Their Applications (Ⅶ) ——Synthesis of 4,4-disubstituted1,7-Difunctional Compounds

LIU Guang-Jian, ZHANG Zheng, WANG Yu-Liang, ZHOU Wei-Qing, ZHANG Li-Kang, BAI Ya-Luo   

  1. Department of Chemistry, Nanjing University, Nanjing, 210008
  • Received:1992-05-17 Revised:1992-12-26 Online:1993-05-24 Published:1993-05-24

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摘要： 通过α-芳基磺酰基乙酸乙酯与α,β-不饱和酯、腈、酮在温和条件下进行双共轭加成反应一锅法高产率地合成了一系列1,7-二官能团化合物,对它们的结构作了表征,初步讨论了Michael受体、相转移催化剂和溶剂对该双共轭加成反应的影响。

关键词: &alpha, -芳磺酰基乙酸醋, 固-液相转移催化, 双重共轭加成, 合成, 取代1, 7-二官能团化合物

Abstract: 1,7-Difunctional compounds and some of their derivatives are of considerable importance in both of synthetic chemistry and fine chemical industry.This paper reports a facile and efficient one-pot synthesis of substituted 1,7-dif unctional compounds via the double conjugate addition of α-arylsul-fonylacetates (1-4) to the α, β-unsaturated esters (5,8-10), nitrile (6) and ketone (7) under very mild conditions.Eight new substituted 1,7-difunctional compounds (14-21) including 1,7-heptanedioic acid esters (14, 17, 21), 1,7-heptanedinitrile (15), 2,8-nonanone (18), 7-oxo-oc-tanoate (19) were synthesized and fully characterized, the yields are excellent.The effects of Michael acceptors, phase-transfer catalyst and solvents on the double conjugate addition were also discussed briefly.

Key words: α-Arylsulfonylacetates, Solid-liquid phase-transfer catalysis, Double conjugate addition, Synthesis, Substituted 1,7-difunctional compounds

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