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有机化学
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有机化学 ›› 1988, Vol. 8 ›› Issue (2): 110-114. 上一篇    下一篇

综述与进展

Dane 盐-甲亚服法合成单环β-内酰胺的研究

苟大明、毛文仁.   

  • 发布日期:1988-04-25

Studies on the Synthesis of Monocyclic β-Lactams via "Dane Salt"Azomethine
method

GOU Da-Ming, MAO Wen-Ren.   

  • Published:1988-04-25

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用Dane 盐与不同取代的二苯甲亚胺环合，制备了11 种未见报道的α-院氨基-ß-内联肢，研究了二苯甲亚
胶的取代基对成环反应的影响，用逐步回归分析方法建立了环合反应收率与二苯甲亚胺上取代基的取代常数之间
的相关关系。研究表明，环合收率与二苯甲亚胺上取代基的电性效应常数σ 值呈负的线性关系，与甲亚胺的pK.
值呈正的线性关系。利用取代基的σ 值和甲亚胺的pKa 值可以预测同系列化合物成环反应活性的相对高低。

The α-amido-β-lactams were synthesized via annulatíon of "Dane Salt" with substituted
benzylideneanilines in the presence of ethyl chloroformate and triethylamine. The influence
of substituents of the benzyIideneaniIine on cyclization was studied. The rrelatiòn between
the aromatic substituent constantσand the yields of cyclízation products was estab1ished
by Stepwise Regression Analysís. The yields of cyclization products showed a negative línear
correlation with σbut a positive línear correlation with pK. of azomethines. These properties
might be useful in the prediction of the relative reactivity of cyclization of "Dane Salt" with
azomethines.