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有机化学
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有机化学 ›› 2008, Vol. 28 ›› Issue (07): 1282-1286. 上一篇    下一篇

研究简报

具有1,2-二苯基乙醇结构化合物的异常消除反应研究

金蔚蔚; 吴文彦; 张 倩*; 夏 鹏*   

  1. (复旦大学药学院药物化学教研室 上海 200032)
  • 收稿日期:2007-09-05 修回日期:2008-01-25 发布日期:2008-07-28
  • 通讯作者: 张 倩*; 夏 鹏

Unexpected Elimination Reaction of the Compounds with 1,2-Diphenylethanol Scaffold

JIN, Wei-Wei ; WU, Wen-Yan ; ZHANG, Qian*; XIA, Peng*   

  1. (Department of Medicinal Chemistry, School of Pharmacy, Fudan University, Shanghai 200032)
  • Received:2007-09-05 Revised:2008-01-25 Published:2008-07-28
  • Contact: ZHANG, Qian*; XIA, Peng*

PDF

722

被引次数

3

报道了4个具有1,2-二苯基乙醇结构的化合物在酸性条件下发生消除反应, 得到未遵循Saytzeff规则的烯烃; 而在SOCl2/DMF条件下, 先氯代再消除则可获得一对双键位置异构的烯烃异构体. 通过计算机模拟, 采用Gaussian 98软件, B3LYP/6-31G方法对两种异构体进行了能量优化, 计算了它们的能量, 推测这类具有1, 2-二苯基乙醇结构化合物在酸性条件下的异常消除反应为动力学主导产物的反应.

关键词: 消除反应, 热力学反应, 动力学反应, 1,2-二苯基乙醇

The elimination of four alcohols with 1,2-diphenylethanol scaffold catalyzed by various acids afforded the unexpected alkenes respectively, which were not the products following Sayzteff’s rule. When employing SOCl2/DMF, the elimination resulted in a pair of isomers with the double-bond at different positions. The energy of the two isomers was calculated via a computer-aided method using Gaussian 98 and B3LYP/6-31G, showing that the elimination of this kind of alcohols in the presence of acid could relate to a kinetic mechanism.

Key words: elimination reaction, kinetics reaction, thermodynamics reaction, 1,2-diphenylethanol