摘要1,1-二芳基乙烷骨架存在于许多具有生物活性的分子中，该类化合物的合成受到了化学工作者的广泛关注。本文研究了在消旋磷酸催化下，结构普通的邻羟基苯乙烯与吲哚的反应，高效高产率地合成了一系列具有结构多样性的1,1-二芳基乙烷类化合物（产率高达99%）。该反应是基于邻羟基苯乙烯在消旋磷酸催化下异构化成邻亚甲基苯醌中间体，通过消旋磷酸对该中间体和吲哚的双氢键活化模式，实现该反应的高效性。该反应条件温和，底物适用性广，不仅为解决金属催化带来的金属残留、反应条件苛刻等问题提供了有效的策略，同时也拓展了利用有机小分子催化来合成1,1-二芳基乙烷类化合物的反应适用范围。50776

该论文有图6幅，表5个，参考文献24篇。

毕业论文关键词：布朗斯特酸催化;  有机小分子催化;  1,1-二芳基乙烷;  邻羟基苯乙烯; 吲哚;  邻亚甲基苯醌

Brønsted Acid Catalyzed Reaction of ortho-Hydroxylstyrenes with Indoles based on ortho-Quinone methide

Abstract

 The skeleton of 1,1-diarylethane exists in many biologically important molecules. So, the synthe-sis of 1,1-diarylethanes has absorbed great attention from the chemists. This work has established a reaction of ortho-hydroxylstyrenes with indoles in the presence of racemic phosphoric acid, leading to the efficient synthesis of a series of 1,1-diarylethanes with structural persity in high yields (up to 99%). This reaction is based on the fact that ortho-hydroxylstyrenes could transform into ortho-quinone methide under the catalysis of racemic phosphoric acid. The dual activation mode of racemic phosphoric acid to ortho-quinone methide and indole via forming two hydrogen bonds contributed greatly to the efficiency of the reaction. The mild reaction condition and wide substrate scope of the reaction will not only provide a useful strategy for solving the problems of residual metal and harsh reaction condition associated with metal catalysis, but also expand the applicability of organocatalytic reactions for the synthesis of 1,1-diarylethanes.

Key Words: Brønsted acid catalysis;  organocatalysis;  1,1-diarylethane; ortho-hydroxylstyrene;  indole;  or-tho-quinone methide

摘要Ⅰ

Abstract-Ⅱ

目录Ⅲ

图清单-Ⅳ

表清单-Ⅳ

1 绪论1

2结果与讨论3

2.1反应条件的筛选3

2.2反应的底物适用范围5

3 实验部分-6

3.1仪器与试剂6

3.2实验方法-6

3.3化合物的表征-7

4结论12

参考文献13

致谢16

 图清单

图序号 图名称 页码

图1 1,1-二芳基乙烷的衍生物 1

图2 1,1-二芳基乙烷类化合物 1

图3 含有吲哚母核的1,1-二芳基乙烷类化合物合成过程 2

图4手性的1,1,1-三芳基乙烷类化合物的合成 2

图5 各类布朗斯特酸 3

图6 1,1-二芳基乙烷类化合物的合成 5

表清单

表序号 表名称 页码

表1 催化剂种类对反应的影响 3

表2 不同溶剂对反应的影响