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有机化学
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有机化学 ›› 2009, Vol. 29 ›› Issue (9): 1440-1444. 上一篇    下一篇

研究简报

1-(2-氰乙基)-2-氧代环戊基甲酸甲酯的选择性水解脱羧

赵广乐a 于 亮b 闫喜龙a 王东华b 陈立功*,a   

  1. (a天津大学化工学院 天津 300072)
    (b天津大学药物科学与技术学院 天津 300072)
  • 收稿日期:2009-01-05 修回日期:2009-03-04 发布日期:2009-12-30
  • 通讯作者: 陈立功

Selective Hydrolysis and Decarboxylation of Methyl [1-(2-Cyanoethyl)-2-oxocyclopentyl]carboxylate

Zhao, Guangle a Yu, Liang b Yan, Xilong a Wang, Donghua b Chen, Ligong *,a   

  1. (a School of Chemical Engineering and Technology, Tianjin University, Tianjin 300072)
    (b School of Pharmaceutical Science and Technology, Tianjin University, Tianjin 300072)
  • Received:2009-01-05 Revised:2009-03-04 Published:2009-12-30
  • Contact: Chen, Ligong

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被引次数

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对1-(2-氰乙基)-2-氧代环戊基甲酸甲酯(4)的选择性水解脱羧反应进行了系统研究. 发现上述化合物在碱的催化作用下主要生成开环副产物2-(2-氰乙基)己二酸二甲酯及2-(2-氰乙基)己二酸; 由于氰基在酸性介质中也可发生水解, 因此对1-(2-氰乙基)-2-氧代环戊基甲酸甲酯在酸性情况下水解脱羧的反应条件进行了探索, 发现在4 mol•L－1盐酸介质中, 50 ℃下反应24 h, 以84.0%的收率得到目标产物3-(2-氧代环戊基)-丙腈.

关键词: 1-(2-氰乙基)-2-氧代环戊基甲酸甲酯, 3-(2-氧代环戊基)-丙腈, 水解, 脱羧

Selective hydrolysis and decarboxylation of methyl [1-(2-cyanoethyl)-2-oxocyclopentyl]- carboxylate (4) were studied. The ring-opened byproducts, dimethyl-2-(2-cyanoethyl)adipate and 2-(2-cyanoethyl)adipic acid, were obtained primarily in an alkaline medium. While, in an acid medium, the hydrolysis and decarboxylation of 4 were studied since the cyano group could also be hydrolyzed. 3-(2-Oxocyclopentyl)propanenitrile was yielded in 84.0% at 50 ℃ after 24 h in the medium of 4 mol•L－1 HCl after optimization.

Key words: 3-(2-oxocyclopentyl)propanenitrile, hydrolysis, decarboxylation, methyl [1-(2-cyanoethyl)-2-oxocyclopentyl]carboxylate