大学化学 >> 2023, Vol. 38 >> Issue (1): 220-226.doi: 10.3866/PKU.DXHX202203020

化学实验 上一篇    下一篇

基于氢键诱导理论的有机化学探索实验：(+/−)-2-亚甲基香茅醛的合成与快速鉴定

金剑1, 杨雪苹1, 程景1, 任鹏2,*()   

  1. 1 哈尔滨工业大学(深圳)实验与创新实践教育中心, 广东 深圳 518055
    2 哈尔滨工业大学(深圳)理学院, 广东 深圳 518055
  • 收稿日期:2022-03-10 录用日期:2022-05-06 发布日期:2022-05-12
  • 通讯作者: 任鹏 E-mail:renpeng@hit.edu.cn
  • 基金资助:
    哈尔滨工业大学(深圳)2018年创新实验课立项

Exploratory Organic Chemistry Experiment Based on Hydrogen Bond Induction Theory: Synthesis and Rapid Identification of (+/−)-2-Methylenecitronellal

Jian Jin1, Xueping Yang1, Jing Cheng1, Peng Ren2,*()   

  1. 1 Education Center of Experiments and Innovations, Harbin Institute of Technology (Shenzhen), Shenzhen 518055, Guangdong Province, China
    2 School of Science, Harbin Institute of Technology (Shenzhen), Shenzhen 518055, Guangdong Province, China
  • Received:2022-03-10 Accepted:2022-05-06 Published:2022-05-12
  • Contact: Peng Ren E-mail:renpeng@hit.edu.cn

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摘要：

本实验用吡咯烷和4-二甲基氨基苯甲酸作为有机小分子催化剂，催化天然香料(+/−)-香茅醛与甲醛的Aldol缩合反应并脱水合成(+/−)-2-亚甲基香茅醛。基于小分子催化的氢键诱导效应，我们选用二氯甲烷、四氢呋喃、无水乙醇三种溶剂进行平行反应，用薄层色谱法监控平行反应的转化速度，筛选相对最佳反应溶剂。同时，我们用共振离域理论解释原料和产物在核磁共振化学位移、薄层色谱比移值、液相色谱保留时间的差异。本实验弥补了有机化学实验在反应条件优化方面的空白。

关键词: 小分子催化剂, Aldol反应, 氢键诱导效应, 最佳反应溶剂

Abstract:

In this experiment, pyrrolidine and 4-dimethylaminobenzoic acid were used as organic small molecule catalysts to catalyze the Aldol condensation and dehydration of natural fragrance (+/−)-citronellal with formaldehyde to synthesize (+/−)-2-methylene citronellal. Based on the hydrogen bond induction effect, the solvents dichloromethane, tetrahydrofuran, and anhydrous ethanol were selected for use in parallel reactions. All the reactions were monitored by thin-layer chromatography, and the relatively optimal reaction solvent was determined. Simultaneously, we used the resonance delocalization theory to explain the difference in the NMR chemical shifts, thin layer chromatography ratio shifts, and liquid chromatography retention times of raw materials and products. This experiment fills the gap in the optimization of reaction conditions in organic chemistry experiments.

Key words: Organic small molecule catalysts, Aldol condensation, Hydrogen bond induction effect, Optimal reaction solvent