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化学学报
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化学学报 ›› 2006, Vol. 64 ›› Issue (17): 1843-1846. 上一篇    下一篇

研究论文

经由o-Quinonemethide的trans-Hexahydrocannabinol的简便合成

陆占国*   

  1. (哈尔滨商业大学化学中心 哈尔滨 150076)
  • 投稿日期:2005-03-03 修回日期:2005-07-15 发布日期:2006-09-14
  • 通讯作者: 陆占国

A Facile Synthesis of trans-Hexahydrocannabinol via an o-Quinonemethide

LU Zhan-Guo*   

  1. (Chemical Center, Harbin University of Commerce, Harbin 150076)
  • Received:2005-03-03 Revised:2005-07-15 Published:2006-09-14
  • Contact: LU Zhan-Guo

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建立了一个在质子性溶剂中经由o-quinonemethide中间体的trans-hexahydrocannabinol的简便合成方法. 用对甲苯磺酸为催化剂, 加热回流resorcinol衍生物和citronellal之间偶联产物的甲醇溶液, 酚的脱保护、o-quinonemethides的生成以及分子内狄尔斯-阿尔德环加成反应一步完成, 产率为93%～95%.

关键词: o-quinonemethide, Diels-Alder反应, trans-hexahydrocannabinol

A simple synthesis of trans-hexahydrocannabinol via an o-quinonemethide in protic solvent was established. The methanol solution of coupling product of a resorcinol derivatives and citronellal was refluxed in the presence of p-methylbenzenesulforic acid as an catalyst, the deprotection of phenols, production of o-quinonemethides and intramolucular Diels-Alder cycloaddition reaction took place in one step, in 93%～95% yield.

Key words: o-quinonemethide, Diels-Alder reaction, trans-hexahydrocannabinol