基于培养本科生创新应用能力的“黄酮类化合物的化学合成”综合化学实验的开发与实践

Development and Practice of Comprehensive Chemistry Experiment “Chemical Synthesis of Flavonoids” with the Aim of Cultivating Undergraduate Students’ Innovation and Application Capabilities

摘要: 黄酮类化合物是一类重要的天然有机化合物，有抗癌、抗氧化、抗炎、降低血管脆性等多种药理作用，长期以来备受人们的关注。本文设计以邻羟基苯乙酮与苯甲酰氯为原料的“黄酮化合物的化学合成”综合性实验，不仅让学生巩固抽滤、干燥、过滤及重结晶等基本实验操作，而且可以进一步加深理解有机化学中Baker-Venkataraman分子重排反应理论知识和酮式–烯醇互变的现象。学生可操作自动熔点分析仪、傅里叶变换原位红外光谱仪、核磁共振光谱仪、质谱仪等分析仪器，对中间体和产物的结构进行表征。从基础实验和结构谱分析入手，进行有机化合物合成一般过程的实践操作，巩固和拓展有机化学的理论知识，有助于培养学生的动手实践能力和创新应用能力。

Abstract: Flavonoids are an important class of natural organic compounds with various pharmacological effects such as anti-cancer, anti-oxidation, anti-inflammatory, and reducing vascular fragility, etc., which have attracted a great deal of attention for a long time. We designed a comprehensive experiment of “chemical synthesis of flavonoids” using o-hydroxyacetophenone and benzoyl chloride as raw materials, which not only allows students to consolidate basic experimental operations such as suction filtration, drying, filtration, and recrystallization, but also further deepen their understanding of the Baker-Venkataraman molecular rearrangement reaction and enol-keto tautomerization in organic chemistry. Students can operate automatic melting point analyzer, fourier transform in-situ infrared spectrometer, nuclear magnetic resonance spectrometer, mass spectrometer and other analytical instruments to characterize the structure of intermediates and products. Starting from basic experiments and structural spectrum analysis, practical operation from the general process of synthesis of organic compounds can consolidate and expand the theoretical knowledge of organic chemistry, which will help cultivate students’ hands-on practical ability and research and innovation ability.