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化学学报
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化学学报 ›› 2003, Vol. 61 ›› Issue (3): 411-415. 上一篇    下一篇

研究论文

手性4-取代丁内酯类化合物的合成及其结构研究

王建平;常新红;田欣哲;陈庆华   

  1. 洛阳师范学院化学系
  • 发布日期:2003-03-15

Studies on the Synthesis and Structure of Chiral 4-Substituted- butyrolactone Derivatives

Wang Jianping;Chang Xinhong;Tian Xinzhe;Chen Qinghua   

  1. Department of Chemistry,Luoyang Normal University
  • Published:2003-03-15

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被引次数

13 | 2

脂肪族伯胺和伯醇作为亲核试剂5与5-L-孟氧基丁烯内醋（4）手性合成子通过 不对称Michael加成，得到代-丁内酯类化合物6（44％-57％，ee≥98％）．通过元 素分析，[α]_D~(20)，IR，1~H NMR，了它们的化学结构、立体构型、绝对构型． 可以为某些具有生物活性的化合物及复杂分子的合成提供新的途径．

关键词: 丁内酯, 迈克尔加成反应, X射线衍射分析, 伯胺, 醇, 元素分析, 红外分光光度法, 质子磁共振谱法, 生物活性

The novel chiral compounds 6 have been synthesized in 44%-57% yields with ee ≥98% by asymmetric Michael addition of chiral synthon, 5-L-menthyloxy-butenolides (4) with aliphatic primary amine and primary alcohol 5 as nucleophilic reagents. The structure and absolute configuration were established on the basis of their elemental analysis and spectroscopic data, such as [a]_D~(20), IR, 'H NMR, (13) ~C NMR, MS and X-ray crystallography. These results provide a valuable synthetic route to some complex molecules and biological active compounds.

Key words: butyrolactone, MICHAEL ADDITION REACTION, XRD, PRIMARY AMINE, ALCOHOL, ELEMENTAL ANALYSIS, IR, 1HNMR, BIOLOGICAL ACTIVITY

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