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化学学报
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化学学报 ›› 1999, Vol. 57 ›› Issue (5): 538-540. 上一篇    

研究论文

新手性源5-(l-孟氧基)-3-溴-2(5H)-呋喃酮的合成和结构

黄慧;陈庆华   

  1. 北京师范大学化学系.北京(100875)
  • 发布日期:1999-05-15

The synthesis and structure of novel chiral intermediate, 5-(l- menthyloxy)-3-bromo-2(5H)-furanone

Huang Hui;Chen Qinghua   

  1. Beijing Normal Univ., Dept of Chem..Beijing(100875)
  • Published:1999-05-15

PDF

301

被引次数

30

文中深入研究了5-(l-孟氧基)-3-溴-2(5H)-呋喃酮新手性源(5a)的合成方法及其不对称合成反应。5a不仅制备方法简便,光学纯度单一,而且它作为稳定的Michael受体,可与碳、氧、氮、硫等不同的亲核试剂发生串联的Michael加成/分子内亲核取代反应,制备得到含有多个手性中心的双环[3.3.0^3^,^7]-5-辛烯类化合物、双环[3.1.0^3^,^5]-己烷类化合物和螺-环丙烷类化合物。本文报道了该手性呋喃酮5a的合成和构型测定。

关键词: 呋喃酮P, 溴化合物, 晶体结构, 双环化合物

In this paper, the synthetic method of the novel chiral intermediate, 5-(l-menthyloxy)-3-bromo-2(5H)-furanone (5a) possessing special structural properties and asymmetric reaction of 5a are investigated. The epimeric mixture of 5-(l-menthyloxy)-3-bromo-2(5H)-furanone (5a+5b) was prepared in 92% yield via bromination of epimeric mixture of 5-(l-menthyloxy)-2(5H)-furanone (3a+3b) followed by elimination of hydrogen bromide. After 2-3 recrystallizations from petroleum ether, the optically pure 5a was obtained in 46% yield with d.e≥98%. Its structure and configuration wee established on the basis of the analytical and spectroscopic data, such as [α]D~2~0, UV, IR, ^1H NMR, ^1^3C NMR, MS and X-ray crystallography.

Key words: FURANONE P, BROMINE COMPOUNDS, CRYSTAL STRUCTURE, BICYCLIC COMPOUND

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