大学化学 >> 2022, Vol. 37 >> Issue (2): 2105004.doi: 10.3866/PKU.DXHX202105004

所属专题: 化学实验教学和管理

化学实验 上一篇    下一篇

过渡金属催化的6-苯基-5, 6-二氢-2H-吡喃-2-酮的合成——推荐一个大学有机化学综合实验

刘治彤, 赵子逸, 彭渤, 曲玥名, 田松麟, 俞寿云()   

  • 收稿日期:2021-05-02 录用日期:2021-06-17 发布日期:2021-07-01
  • 通讯作者: 俞寿云 E-mail:yushouyun@nju.edu.cn
  • 作者简介:俞寿云, Email: yushouyun@nju.edu.cn
  • 基金资助:
    南京大学“科研融合型”高阶实验课程培育项目

Transition-Metal-Catalyzed Synthesis of 6-Phenyl-5, 6-dihydro-2H-pyran-2-one: A Comprehensive Organic Experiment for Undergraduate Students

Zhitong Liu, Ziyi Zhao, Bo Peng, Yueming Qu, Songlin Tian, Shouyun Yu()   

  • Received:2021-05-02 Accepted:2021-06-17 Published:2021-07-01
  • Contact: Shouyun Yu E-mail:yushouyun@nju.edu.cn

摘要:

有机合成中,碳-碳键的形成和断裂是一个永恒的热门话题,科学家为此发展了很多形成碳-碳键的方法。在这一领域,诞生了不少诺贝尔化学奖的成果,格氏反应和烯烃复分解反应就是其中的经典案例。烯烃复分解反应提供了一种连接sp2-碳和sp2-碳的全新思路,发展出了一些活性分子全合成的高效路径。因而,2005年的诺贝尔化学奖授予了对烯烃复分解反应有杰出贡献的三位科学家。本有机化学综合实验由三个反应构成,包括改进的格氏反应、DMAP催化的酯化反应和关环烯烃复分解反应。每一个反应都可独立成为一个基础有机化学实验,三步的连续反应可以作为一个综合多步合成实验。本实验有助于理解有机合成的过程和机理,体验有机合成的魅力。

关键词: 烯烃复分解反应, 格氏反应, 酯化反应, 碳-碳键形成

Abstract:

The connection and fragmentation of carbon-carbon bond is always a hot topic in organic synthesis, and scientists have been finding different ways to achieve this goal. Many achievements have been made in this field. Grignard reaction and olefin metathesis reaction are the famous and typical ones. In particular, olefin metathesis provides a new way to connect sp2 carbon and sp2 carbon, which suits some active molecules. Therefore, the 2005 Nobel Prize in Chemistry was awarded to three scientists who made outstanding contributions to olefin metathesis. This experiment is consisted of three reactions, including the improved Grignard reaction, DMAP-catalyzed esterification, and ring closing olefin metathesis cyclization. It is helpful to understand the process and mechanism of organic reactions and enjoy the charm of organic synthesis.

Key words: Olefin metathesis, Grignard reaction, Esterification, Carbon-carbon bond formation

MSC2000: 

  • G64