论文总字数：23695字

摘 要

二氧化碳的排放问题已经演化为全球范围内的生态、经济、政治问题，因此，采取有效措施来遏制大气中二氧化碳浓度的持续增长已经迫在眉睫。其中，固定二氧化碳并以之为原料合成各类精细化学品是一种理想的解决方案，而利用二氧化碳与端炔的羧基化反应制备炔酸是目前的研究热点之一。然而，羟基的存在会干扰二氧化碳与末端炔烃的羧基化反应，因此目前尚不能通过炔丙醇与二氧化碳的羧基化反应制备相应的炔酸。在本文中，我们设计了一条“官能团保护-羧基化反应-官能团去保护”的合成路线，首先通过酯基化官能团保护的方法保护羟基，再利用银盐催化炔丙醇酯的羧基化反应，最后脱除保护基，最终成功地制备出一系列同时包含羟基、羧基、不饱和键等丰富官能团的目标炔酸类化合物。

关键词：末端炔烃；炔酸；羧基化；羟基；官能团保护

Abstract

The problem of carbon dioxide emissions has evolved into a global ecological, economic, and political issue. Therefore, it is urgent to take effective measures to curb the continuous increase in the concentration of carbon dioxide in the atmosphere. Among them, fixing carbon dioxide and using it as a raw material to synthesize various fine chemicals is an ideal solution, and the use of carbon dioxide for the carboxylation of terminal alkynes to prepare acetylenic acids is one of the current research hotspots.However, the presence of hydroxyl groups can interfere with the carboxylation reaction of carbon dioxide and terminal alkynes, so it is currently not possible to produce the corresponding acetylenic acids by the carboxylation reaction of propargyl alcohols with carbon dioxide. In this article, we designed a "functional group protection-carboxylation reaction-functional group deprotection" synthetic route, first protected the hydroxyl groups by the method of esterification of functional group protection, and then used the silver salts to catalyze the carboxylation of propargyl alcohol esters, finally, the protecting group was removed, and a series of target alkanoic acid compounds containing rich functional groups such as hydroxyl, carboxyl, and unsaturated bonds were successfully prepared.

Key Words: Terminal alkyne; acetylenic acid; carboxylation; hydroxyl group; functional group protection

目 录

摘要...............................................................................................................................................Ⅰ

ABSTRACT...................................................................................................................................Ⅱ

第1章绪论......................................................................................................................................1

1.1二氧化碳的排放现状分析....................................................................................................1

1.2二氧化碳浓度剧增的影响....................................................................................................2

1.3二氧化碳的利用现状分析....................................................................................................3

1.4选题思路与主要研究内容....................................................................................................4

1.4.1二氧化碳的性质.............................................................................................................4

1.4.2主要研究内容.................................................................................................................5

第2章 二氧化碳与炔醇合成羟基炔酸........................................................................................7

2.1前言........................................................................................................................................7

2.2.1炔烃的羧基化反应.........................................................................................................7

2.1.2炔醇与二氧化碳的成环反应.........................................................................................7

2.1.3羟基基团在有机合成中的性质.....................................................................................8

2.2立题思路................................................................................................................................9

第3章 实验部分..........................................................................................................................11

3.1实验仪器与试剂..................................................................................................................11

3.2 实验的操作方法.................................................................................................................11

3.2.1炔醇的酯化反应...........................................................................................................11

3.2.2末端炔烃的羧化反应...................................................................................................12

3.2.3炔酸酯的水解反应.......................................................................................................13

第4章 结果与讨论......................................................................................................................14

4.1酯化反应..............................................................................................................................14

4.2羧基化反应..........................................................................................................................15

4.3水解反应..............................................................................................................................17

第5章 总结与展望......................................................................................................................19

参考文献.......................................................................................................................................20

致谢...............................................................................................................................................22

第1章 绪论

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