摘要 ：β-羰基硫醚是有机合成中的一种重要骨架，是重要的有机合成中间体，而且它很容易转变为α，β-不饱和酮。有些β-羰基硫醚可以做香料，在天然产物及药物的合成、饮料、食品和化妆品领域都有广泛的应用。这次试验的目标就是找到一种操作简单又经济的合成路线。而合成的反应中涉及到了串联的Meyer-Schuster重排反应，分子中的巯基发生改变。实验过程中，首先自己合成了一种实验所需的反应物苄硫醇。是通过买来的苄醇→苄氯→苄硫醇。再经过条件筛选找到最终反应的条件，得出在Bi(OTf)3当催化剂的情况下选用二噁烷当溶剂，催化剂当量15(mol%)，苄硫醇当量1。2的情况下反应得到的产率最高。之后就进行了三组实验，每组实验重复多次，准备合成三种β-羰基硫醚类化合物，然而实际只有两组成功的合成了理想产物，另外一组并没有发生反应。而成功的反应的产率很高，本β-羰基硫醚的制备方法最高产率可达99%。本具有操作简单和100%原子经济等优点，为β-羰基硫醚类化合物的构建提供了一种全新的合成方法。80553

毕业论文关键词 ： 串联的Meyer-Schuster重排反应；β-羰基硫醚 ；苄硫醇

Study on Meyer - Schuster Reaction / Intermolecular Hydrogenation in Series

Abstract: β-carbonyl sulfide is an important skeleton in organic synthesis, is an important organic synthesis intermediates, and it is easy to change to α, β-unsaturated ketone。 Some beta-carbonyl sulfides can be used spices, in the natural products and pharmaceutical synthesis, beverage, food and cosmetics have a wide range of applications。 The goal of this experiment is to find a simple and economical synthetic route。 The synthesis of the reaction involves a series of Meyer-Schuster rearrangement reaction, the molecular thiol group changes。 In the course of the experiment, we first synthesized a kind of reactant benzyl mercaptan for the experiment。 Is by buying benzyl alcohol → benzyl chloride → benzyl mercaptan。 And then the conditions of the final reaction were found by the conditional screening。 The yield of dioxane was determined when Bi (OTf) 3 was used as the catalyst, the catalyst equivalent was 15 mol% and the benzyl mercaptan equivalent 1。2 The highest rate。 After three experiments were carried out, each experiment was repeated several times to prepare the synthesis of three β-carbonyl sulfide compounds, but only two groups of successful synthesis of the ideal product, the other group did not react。 And the yield of the successful reaction is very high。 The highest yield of the β-carbonyl sulfide is 99%。 This has the advantages of simple operation and 100% atomic economy, and provides a new synthesis method for the construction of β-carbonyl sulfide compounds。

Key words :Meyer-Schuster rearrangement reaction,In tandem ;  beta-carbonyl sulfide ; Benzyl mercaptan

目录

第一章 绪论

1。1 引言

1。2  Meyer-Schuster重排反应

1。2。1  Meyer-Schuster重排反应的概述

1。3 串联反应

1。3。1 Robinson增环反应

1。3。1。1 Michael加成反应

1。3。1。2 反应原理

第二章 原料的制备

2。1苄硫醇

2。1。1介绍

2。1。2苄硫醇的制备

2。1。3条件筛选

第三章β-羰基硫醚的合成

3。1。 β-羰基硫醚

3。1。1 介绍

3。1。2 两种主要合成方法

3。1。3 β-羰基硫醚的制备方法

3。1。4 实验步骤

3。1。5 三组β-羰基硫醚的合成实验