科研成果转化为有机化学教学实验之探索

发布时间：2018-05-08 01:26

本文选题：有机化学 + 科研成果　；参考：《实验室研究与探索》2017年11期

【摘要】：探索了从较为成熟的药物合成科研实验"潜手性化合物的去对称化反应"设计转化成有机化学综合教学实验。采用金鸡纳生物碱奎宁(QN)作为有机小分子催化剂,对(+)-生物素合成中间体内消旋环酸酐(CAN)的不对称甲醇解反应进行了探索与优化,并通过红外光谱、核磁共振和比旋光度等手段进行产物结构的表征。最后,采用非对映体结晶拆分的方法对催化剂奎宁进行回收再利用。该实验可以帮助学生巩固不对称催化合成和化学拆分法的基本原理,掌握旋转蒸发仪、薄板层析、红外光谱仪、核磁共振仪等仪器的工作原理及操作技能,培养学生相关的基础有机化学知识、合成实验操作、谱图解析等方面的综合研究能力,有利于给学生树立绿色化学的教学理念。
[Abstract]:This paper explores the transformation from a mature drug synthesis experiment, "Desymmetry reaction of latent chiral compounds", to a comprehensive teaching experiment of organic chemistry. The asymmetric methanol hydrolysis reaction of racemic cyclic anhydride (CAN) was investigated and optimized by using quinine (quinine) as a small organic catalyst in the synthesis of alkaloids. The structure of the product was characterized by NMR and specific optical rotation. Finally, the catalyst quinine was recovered and reused by the method of enantiomeric crystallization resolution. This experiment can help students to consolidate the basic principles of asymmetric catalytic synthesis and chemical resolution, and master the working principle and operation skills of rotating evaporator, thin plate chromatography, infrared spectrometer, nuclear magnetic resonance instrument, etc. Cultivating the students' comprehensive research ability of basic organic chemistry knowledge, synthetic experiment operation, spectrum analysis and so on is helpful to set up the teaching idea of green chemistry for the students.
【作者单位】：上海理工大学化学系;
【基金】：国家自然科学基金(81172918) 上海理工大学2016年度教师教学发展研究项目(CFTD16051Y) 上海市级和上海理工大学校级大学生创新创业训练计划项目(SH2016163、XJ2016226)
【分类号】：G642;O62-4

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