大学化学 >> 2023, Vol. 38 >> Issue (2): 214-220.doi: 10.3866/PKU.DXHX202205061

化学实验 上一篇    下一篇

香豆素-3-羧酸制备实验的改进与拓展设计

黄言吉1, 刘斌阳1, 余敏1, 林敏2, 周金梅2,*(), 林丽榕1,*()   

  1. 1 厦门大学化学化工学院, 福建 厦门 361005
    2 厦门大学化学国家级实验教学示范中心, 福建 厦门 361005
  • 收稿日期:2022-05-18 录用日期:2022-07-21 发布日期:2022-08-02
  • 通讯作者: 周金梅,林丽榕 E-mail:jmzhou@xmu.edu.cn;linlr@xmu.edu.cn

Improvement and Extensive Design of the Synthesis of Coumarin-3-carboxylic Acid

Yanji Huang1, Binyang Liu1, Min Yu1, Min Lin2, Jinmei Zhou2,*(), Lirong Lin1,*()   

  1. 1 College of Chemistry and Chemical Engineering, Xiamen University, Xiamen 361005, Fujian Province, China
    2 National Demonstration Center for Experimental Chemistry Education, Xiamen University, Xiamen 361005, Fujian Province, China
  • Received:2022-05-18 Accepted:2022-07-21 Published:2022-08-02
  • Contact: Jinmei Zhou, Lirong Lin E-mail:jmzhou@xmu.edu.cn;linlr@xmu.edu.cn

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摘要：

香豆素-3-羧酸的制备是一个经典实验，一般是以水杨醛和丙二酸二乙酯为原料，在哌啶催化下加热回流2 h，经过两步完成。我们对该实验进行了以下改进与拓展：1) 以水杨醛和米氏酸为原料，水为溶剂，在90 ℃下加热搅拌30 min，即可得到香豆素-3-羧酸；同时改变底物实现7-(二乙氨基)香豆素-3-羧酸的制备；2) 通过观察香豆素-3-羧酸和7-(二乙氨基)香豆素-3-羧酸与稀土离子Eu3+混合溶液的荧光，引入计算化学验证香豆素-3-羧酸和7-(二乙氨基)香豆素-3-羧酸对Eu3+的能量转移性质。本实验涉及多个学科的重要知识点，具有较强的模块性、综合性、趣味性、教学可行性，有利于培养学生的创新能力与综合应用能力。

关键词: 香豆素-3-羧酸, Knoevenagel缩合反应, 荧光, 能量转移

Abstract:

The preparation of coumarin-3-carboxylic acid is a classical chemistry experiment. In this experiment, the reactants, salicylaldehyde and diethyl malonate, as well as the piperidine catalyst are mixed under reflux for 2 h to obtain coumarin-3-carboxylic acid after base hydrolysis and acidification. We have made the following improvements and extensive designs to the experiment: 1) By substituting diethyl malonate with Meldrum's acid, coumarin-3-carboxylic acid can be obtained by heating at 90 ℃ for 30 min in water, and 7-(diethylamino)coumarin-3-carboxylic acid can be synthesized by changing the substrate; 2) Observing the fluorescence of the solution with Eu3+, coumarin-3-carboxylic acid, and 7-(diethylamino)coumarin-3-carboxylic acid and using computational chemistry can help verify the energy transfer property. The modified experiment, which involves a number of important multidisciplinary knowledge points, has strong modularity, comprehensiveness, interest, and teaching feasibility. Moreover, it is conducive to cultivating students' innovative and comprehensive application abilities.

Key words: Coumarin-3-carboxylic acid, Knoevenagel condensation reaction, Fluorescence, Energy transfer