大学化学 >> 2023, Vol. 38 >> Issue (12): 205-211.doi: 10.3866/PKU.DXHX202304067

化学实验 上一篇    下一篇

甘氨酸催化下串联合成香豆素-3-羧酸

董军(), 陈友威, 常伟, 桑泽矾, 曾子航, 徐国栋()   

  • 收稿日期:2023-04-18 录用日期:2023-06-21 发布日期:2023-06-28
  • 通讯作者: 董军,徐国栋 E-mail:dongj01@yctu.edu.cn;xugd@yctu.edu.cn
  • 基金资助:
    国家自然科学基金(51907173);江苏省高等学校基础科学(自然科学)研究面上项目(22KJB150046)

Tandem Synthesis of Coumarin-3-Carboxylic Acid Catalyzed by Glycine

Jun Dong(), Youwei Chen, Wei Chang, Zefan Sang, Zihang Zeng, Guodong Xu()   

  • Received:2023-04-18 Accepted:2023-06-21 Published:2023-06-28
  • Contact: Jun Dong, Guodong Xu E-mail:dongj01@yctu.edu.cn;xugd@yctu.edu.cn

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摘要：

“香豆素-3-羧酸的制备”是基础有机化学实验中一个经典的任务型教学实验。在实验过程中，我们发现香豆素-3-羧酸的合成步骤繁琐，时间较长，试剂环保性不足。为了提升该实验的有效时长，加强实验过程的绿色环保性，提升实验的拓展性与探究性，我们对该制备反应进行了改进。改进后的实验用水作为溶剂，在回流条件下，以甘氨酸作为催化剂，从丙二酸环(亚)异丙酯与水杨醛出发，实现香豆素-3-羧酸的串联合成。此外，在化合物制备基础上，引入熔点测定、红外以及核磁表征环节，整个实验时长约为4小时，适合有机化学实验本科教学。本次改进实验，以绿色合成为基础，辅以表征环节，有效增加了拓展性。并在此过程中探索线上线下混合式教学模式，增加探究性，进而有效提升学生的科学素养。

关键词: 香豆素-3-羧酸, 甘氨酸, 水杨醛, 丙二酸环(亚)异丙酯, 绿色合成

Abstract:

"Coumarin-3-carboxylic acid preparation" is a classic task-based teaching method used in basic organic chemistry experiments. During the experiment, we found that the synthesis of coumarin-3-carboxylic acid was complicated, time-consuming, consisted of several steps, and the reagents involved were not environmentally friendly. A modification was proposed to increase the effective use of teaching time, realize the greenness of the experimental process, and enhance the extensibility and exploration of the experiment. In an improved experiment, the tandem synthesis of coumarin-3-carboxylic acid was accomplished using Meldrum's acid and salicylaldehyde under reflux conditions in water as the solvent and glycine as the catalyst. Once the compound was prepared, its structure was characterized by melting point analysis, infrared spectroscopy, and nuclear magnetic resonance. The entire experiment lasted for approximately 4 h, which is suitable for teaching undergraduates. This improved experiment was based on green synthesis supplemented by physical characterization, which effectively increased the extensibility. We also explored online and offline mixed teaching models to effectively cultivate students' scientific exploration abilities.

Key words: Coumarin-3-carboxylic acid, Glycine, Salicylaldehyde, 2, 2-Dimethyl-1, 3-dioxane-4, 6-dione, Green synthesis