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有机化学 ›› 1995, Vol. 15 ›› Issue (5): 542-545. 上一篇    下一篇

研究论文

手性亚砜法合成粉 虫性信息素

李焰;徐章煌;黄锦霞;陈祖兴;高明章   

  1. 湖北大学化学系
  • 发布日期:1995-10-25

Synthesis of (+)-sucatol using a chiral sulfoxide

LI YAN;XU ZHANGHUANG;HUANG JINXIA;CHEN ZUXING;GAO MINGZHANG   

  • Published:1995-10-25

5-氯-2-戊酮(2)经四步反应制得(R)-(+)-4-甲基-3-戊烯基对甲苯基亚砜(6), 化合物6与乙醛进行不对称加成反应得手性醇(7), 7经兰尼镍还原性脱硫反应即合成出目标产物粉 虫性信息素(1), 其光学纯度可达45%。

关键词: 粉 虫性信息素, 戊酮, 红外分光光度法, 质子磁共振谱法, 亚砜 P, 性信息素, 脱硫, 还原反应

(R)-(+)-4-Methyl-3-pentenyl p-tolyl sulfoxide (6) was prepared from 5-chloro-2-pentanone (2) in a four-step sequence produced. Asymmestric addition of 6 with acetaldehyde at -10℃ gave optically active alcohol 7 in 85% yield, then (+)-sucatol was synthesized by in 84% yield by reductive desulfurization of 7 with Raney-Ni. The enantiomeric excesse of the target compound 1 is 45% e. e.

Key words: INFRARED SPECTROPHOTOMETRY, PROTON MAGNETIC RESONANCE SPECTROMETRY, PENTANONE, SEX PHEROMONE, DESULFURIZATION, SULFOXIDE P, REDUCTION REACTION

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