Piancatelli重排反应在药物中间体合成中的应用
毕业论文关键字： 重排反应、手性分子、4-羟基环戊烯酮
The application of Piancatelli rearrangement in the Synthesis of medicine intermediate
Abstract：Chiral cyclopentenone is the key intermediate for a lot of active natural products and a variety of drug synthesis. For many years, chemists have used different methods to synthesize this molecule. One of the most prominent molecule is 4-hydroxycyclopentenone. This molecule has a wide range of uses. It can be used as antimicrobial active substance; pharmaceutical intermediates of prostaglandin and so on. At the same time, this molecule is easy to be racemized. And it is unstable. Under some acid-base conditions, it is easy to produce reverse aldol reaction. In this experiment, we use furfural as raw material, and through additive reaction to get the raw material of rearrangement reaction. In this experiment, we use five different reagents to make this reaction, and we pat emphasis on the choice of reaction temperature, and the productivity is about 80-90%. And the through Piancatelli rearrangement reaction, we can get different chiral cyclopentenone molecules. This is the most important step in all the experiments. And because of the complicated mechanism, the productivity of the reaction is not very high, only about 30-50%. And then through enzymatic kinetic resolution; Michael addition reaction and elimination reaction, we can get another pharmaceutical intermediates with higher medicinal value. Based on this foundation, we make a comprehensive analysis about product purity; product quantity; operating conditions; cost; reaction time and green chemistry. We will try our best to optimized the reaction routes.
Key Words：rearrangement reaction； chiral molecule；4-hydroxycyclopentenone
目录
1 绪论 1
1.1 课题背景与意义 1
1.2 Piancatelli重排反应的简介 1
1.2.1 Piancatelli重排反应产物的相关化学信息 2
1.2.2 Piancatelli重排反应的应用价值 2
1.2.3 Piancatelli重排反应方法 2
1.3 本课题主要研究内容 3
1.3.1 Piancatelli重排反应路线的研究现状 3
1.3.2 Piancatelli重排反应路线优化 4
1.4 合成路线拟定 4
2 实验部分 7
2.1 实验试剂和仪器 7
2.1.1 实验试剂 7
2.1.2 实验仪器 7
2.1.3 试剂的物理常数 8
2.2 Piancatelli重排反应机理 8
2.3 4-羟基环戊烯酮的制备 10
2.3.1 以甲基氯化镁为原料制备4-羟基环戊烯酮分子 10