基于自由基过程的三氟甲基化反应探索

摘要近年来，在医药化学、农业药剂以及各种功能材料等领域含有三氟甲基基团的有机化合物变得越来越重要。三氟甲基作为一个重要的含氟基团，具有强吸电子诱导效应、强亲脂性，将基团引入有机分子中将显著改善分子的酸性，亲脂性及代谢稳定性,分子在物理、化学和生物活性上表现出显著变化。本论文探索了自由基过程下的三氟甲基有机化合物的新型合成方法。48043

本文首先采用三氟甲基亚磺酸钠等三氟甲基化试剂在一定催化条件下引发三氟甲基自由基，并与苯甲醛及其衍生物反应，虽然实验没有得到目标产物，但是也积累了宝贵的经验。通过对该反应机理的思考，进一步尝试了肉桂酸与一系列三氟甲基试剂的自由基三氟甲基化方法，并成功合成了高选择性的三氟甲基取代的目标产物。

毕业论文关键词三氟甲基自由基苯甲醛三氟甲基试剂

毕业设计说明书外文摘要

Title Trifluoromethyl-based radical reaction process of exploration

Abstract

In recent years, The trifluoromethylation of organic compounds are increasingly important structural motifs,s uch as the medicical chemistry、agricultural agents and other functional materials. The CF3 group is an important fluoric molecule, possessing strong electronegativity and strong lipophilicity. Among them, compounds containing the CF3 moiety have shown its acidity, lipophilicity and metabolic stability significantly, and there will be great change in its physical, chemical properties and biological activity t in the presence of it. This paper explored a new synthetic method for trifluoromethylated compound through free radical reactions.

A method for CF3SO2Na-based trifluoromethylation via radical conditions under specific conditions with benzaldehyde and its derivatives was first explored in the paper. Although no desired products were obesrved, we had gather valuable experience. Based on the thought of machoism, a trifluoromethylation method using trifluoromethylating reagent with cinnamic acid was developed. Trifluoromethylated products with high selectivity were synthesized.

Keywords CF3 Radical Benzaldehyde Trifluoromethyl reagent

1 引言 1

1.1 含氟有机化合物概述 1

1.1.1 含氟有机化合物简史 1

1.1.2 含氟化合物的特殊性质 1

1.1.3 三氟甲基基团性质研究 2

1.1.4 三氟甲基引入方法 2

1.2 三氟甲基自由基参与的C-C键形成反应 5

1.2.1 三氟甲基化试剂均裂产生三氟甲基自由基 5

1.2.2 三氟甲基试剂在还原剂作用下产生自由基 6

1.2.3 氧化三氟甲基试剂产生三氟甲基自由基 7

1.3 课题研究内容 8

1.3.1 探索用自由基的实验机理活化苯甲醛的C-H键连接三氟甲基自由基反应 8

1.3.2 进一步拓展用自由基机理来使4-甲基肉桂酸脱羧产生自由基的三氟甲基自由基反应 8

2 实验部分 8 基于自由基过程的三氟甲基化反应探索:http://www.751com.cn/huaxue/lunwen_50383.html