大学化学 >> 2015, Vol. 30 >> Issue (3): 43-46.doi: 10.3866/pku.DXHX2010343

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褪黑激素的合成——介绍一个探索性有机化学实验

关玲, 徐烜峰, 边磊, 高杨, 张奇涵   

  1. 北京大学化学基础实验教学中心 北京 100871
  • 发布日期:2015-06-25
  • 通讯作者: 张奇涵 E-mail:zqh@pku.edu.cn

The Synthesis of Melatonin——An Exploratory Organic Chemistry Experiment

Guan Ling, Xu Xuanfeng, Bian Lei, Gao Yang, Zhang Qihan   

  1. Experimental Chemistry Center, Peking University, Beijing 100871, China
  • Published:2015-06-25

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摘要：

介绍一个面向大学二年级本科生的探索性实验。基于专利文献方法的合成路线较为适宜学生实验且具有良好训练价值:以邻苯二甲酰亚胺、1,3-二溴丙烷、乙酰乙酸乙酯、对甲氧基苯胺为基本原料,以Japp-Klingemann 反应和Fischer吲哚合成法联用构建吲哚环,经水解脱羧、乙酰化,合成了褪黑激素。对学生在实验中的条件优化探索进行了简要介绍。

关键词: 探索性实验, 褪黑激素, Japp-Klingemann反应, 多步合成

Abstract:

The synthesis of melatonin is an exploratory experiment completed by second-year undergraduates. The synthetic approach based on the procedure provided by the patent is a short, simple, and industrially feasible process suitable for organic chemistry laboratory. The formation of the indole ring is completed based on Japp-Klingemann reaction and Fischer indole synthesis using phthalimide, 1,3-dibromo-propane, ethyl acetoacetate and 4-anisidine as the main reactants. Melatonin forms after hydrolyzation, decarboxylation and acetylation of the indole ring. The optimization of conditions is also discussed briefly.

Key words: Exploratory experiment, Melatonin, Japp-Klingemann reation, Multi-step synthesis