大学化学 >> 2022, Vol. 37 >> Issue (5): 2110099.doi: 10.3866/PKU.DXHX202110099

所属专题： 第2届全国大学生化学实验创新设计竞赛

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香芹酮的选择性环氧化

李玲, 张学艳, 汪小满, 凌剑, 史勇()   

  • 收稿日期:2021-10-29 录用日期:2021-11-04 发布日期:2022-03-22
  • 通讯作者: 史勇 E-mail:yshi@ynu.edu.cn
  • 作者简介:史勇，Email: yshi@ynu.edu.cn
  • 基金资助:
    云南省教改项目(JG2018025)

Selective Epoxidation of Carvone

Ling Li, Xueyan Zhang, Xiaoman Wang, Jian Ling, Yong Shi()   

  • Received:2021-10-29 Accepted:2021-11-04 Published:2022-03-22
  • Contact: Yong Shi E-mail:yshi@ynu.edu.cn

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摘要：

选择性是有机化学的核心概念之一，也是有机化学研究的关键问题之一。本实验以左旋香芹酮为原料，利用其两个碳碳双键性质的不同，使用两种不同的氧化方式进行选择性环氧化；对香芹酮两个碳碳双键的环氧化体现出化学选择性，而对应的产物是否为异构体混合物则体现出立体选择性。整个实验使用的原料和试剂便宜易得，反应操作简单且后处理容易，产物收率较高，适合本科有机化学实验教学，可帮助学生加深对化学选择性和立体选择性的认识和理解。

关键词: 选择性, 香芹酮, 环氧化, 化学选择性, 区域选择性

Abstract:

Selectivity is a core organic chemistry concept and is often a key issue in organic chemistry research. In this experiment, (R)-(−)-carvone was used as a substrate upon which two oxidation methods were employed to selectively give two different products. The epoxidation of the two double bonds of carvone shows chemoselectivity, while whether the corresponding product is a mixture of isomers shows stereoselectivity. Since this experiment features inexpensive reagents, simple operation and workup procedures, and high yields, it is suitable for organic chemistry experimental teaching, deepening undergraduates' understanding of chemoselectivity and stereoselectivity.

Key words: Selectivity, Carvone, Epoxidation, Chemoselectivity, Stereoselectivity