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有机化学
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有机化学 ›› 2005, Vol. 25 ›› Issue (04): 409-411. 上一篇    下一篇

研究论文

贫电子环丙烷衍生物与2-巯基苯骈噻唑的反应研究

胡吉嵘1，曹卫国*,1,2，丁维钰1，叶青1，高金森1   

  1. (1上海大学化学系 上海 200436)
    (2中国科学院上海有机化学研究所金属有机化学国家重点实验室 上海 200032)
  • 收稿日期:2004-06-22 修回日期:2004-11-01 发布日期:2005-03-30
  • 通讯作者: 曹卫国

Study on the Reaction of Electron-deficient Cyclopro-paneDerivatives with 2-Mercaptobenzothiazole

HU Ji-Rong1,CAO Wei-Guo*,1,2,DING Wei-Yu1,YE Qing1,GAO Jin-Sen   

  1. (2 State Key Laboratory of Organometallic Chemistry, Chinese Academy of Sciences, Shanghai 200032)
  • Received:2004-06-22 Revised:2004-11-01 Published:2005-03-30
  • Contact: CAO Wei-Guo

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被引次数

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贫电子环丙烷衍生物1以精制四氢呋喃为溶剂, 与2-巯基苯骈噻唑(2)封管加热反应, 得到产物3和4. 产物3经IR, MS, 1H NMR, 13C NMR和元素分析等数据确定其结构为: (R)-β-取代-(R)-γ-(2-巯基)苯骈噻唑基-γ-对位取代苯基丁酸或(S)-β-取代-(S)-γ-(2-巯基)苯骈噻唑基-γ-对位取代苯基丁酸(3); 产物4通过IR, MS, 1H NMR, 13C NMR, 2D-NOESY谱和元素分析等数据确定其结构为: 反式-β-取代-γ-对位取代苯基-3-丁烯酸(4). 对生成产物的机理也进行了推测.

关键词: 贫电子环丙烷衍生物, 丁酸衍生物, 多取代-3-丁烯酸衍生物

Electron-deficient cyclopropane derivatives 1 in anhydrous THF reacted with 2-mercaptoben- zothiazole (2) in a sealed tube to give the products 3 and 4 with high yield and stereoselectivity. The structures of 3 and 4 were identified as (R)-β-substituted-(R)-γ-(2-mercaptoben-zothiazolyl)-γ-p-substituted- phenylbutyric acid or (S)-β-substituted-(S)-γ-(2-mercaptobenzothiazolyl)-γ-p-substituted-phenylbutyric acid and trans-β-substituted-γ-p-substituted-phenyl-but-3-enic acid by means of MS, IR, 1H NMR, 13C NMR, 2D-NOESY spectra and elemental analysis. The mechanism for the formation of products was also proposed.

Key words: electron-deficient cyclopropane derivative, polysubsti-tuted-but-3-enic acid, butyric acid derivative