论文总字数：22088字

摘 要

官能化酚类衍生物在合成化学，催化，生物化学和材料科学中具有非常重要的作用。传统的合成方法存在反应条件苛刻、产物去金属化较难，不符合绿色化学理念等缺点。为了实现绿色合成，将官能团选择性引入化合物骨架，我们选择对苯醌单缩酮类化合物（QMAs）作为反应底物。对苯醌单缩酮类化合物是一类同时存在α，β-不饱和羰基和烯丙基缩醛官能团的醌类化合物。由于其独特的结构，这类化合物展现出丰富的化学反应性，可以实现区域选择性合成反应，且其可以从廉价、易得的苯酚类化合物制备而来，因此在有机合成中具有广泛的应用。

本文介绍了对苯醌单缩酮类化合物丰富的化学性质以及多组分反应，总结了对苯醌单缩酮类化合物与不同亲核试剂发生1,2-加成、1,4-加成、烯丙基取代和缩醛取代反应构筑碳-碳键、碳-杂键的研究进展。在课题组前期研究的基础上，本文开展了对苯醌单缩酮类化合物、1-萘酚和脯氨酸的三组分反应制备官能化苯酚类衍生物的研究。通过对反应物比例、反应溶剂等条件的筛选和优化，发展了一种高效高选择性的新型绿色合成方法。与传统方法相比，该方法无需催化剂、反应条件温和、原子利用率高，符合绿色化学的理念，具有重要的应用前景。

关键词：多组分反应 C-N/C-C键构筑 区域选择性 对苯醌单缩酮

ABSTRACT

Functionalized phenol derivatives play an important role in synthesis chemistry, catalysis, biochemistry and materials science. The traditional synthesis method has some shortcomings, such as harsh reaction conditions, difficult product demetallization, not in line with the concept of green chemistry. In order to realize green synthesis, we selected p-quinone monoacetals (QMAS) as the reaction substrate. P-benzoquinone monoketals are one kind of quinones which with the functions of α, β - unsaturated carbonyl and allylic acetal. Because of their unique structures, rich chemical reactivity is showed in these compounds, and regioselective synthesis reaction is able to achieve. Moreover, they can be prepared from cheap and easily available phenol compounds, so p-quinone monoacetals have a wide range of applications in organic synthesis.

In this paper, the rich chemical properties and multicomponent reactions of p-benzoquinone monoketals are introduced. The research progress of 1,2-addition, 1,4-addition of p-benzoquinone monoketals with different nucleophiles, allylic substitution and acetal substitution to form carbon-carbon bond and carbon-hetero bond are summarized. On the basis of the previous research of our group, the preparation of functionalized phenol derivatives by the three-component reaction of p-benzoquinone, 1-naphthol and proline was studied. A new green synthesis method which is high efficiency and regioselectivity has been developed by our group, by selecting and optimizing the reactant proportion, reaction solvent and other conditions. Compared with traditional methods, this method has many advanced, such as: no-catalyst, mild reaction conditions, and high atom utilization rate. All these points conforms to the concept of green chemistry and has an important application prospect.

KEYWORDS：multicomponent reaction C-N / C-C bond construction regioselective p-benzoquinone monoketal

目 录

摘 要 I

ABSTRACT II

第一章 文献综述 1

1.1 研究背景 1

1.2 对苯醌单缩酮类化合物（QMAs）的介绍 1

1.3 QMAs参与的官能化酚类衍生物的合成 2

1.4 多组分反应 7

1.5 研究目的 8

第二章 实验部分 10

2.1 实验仪器与实验试剂 10

2.2 实验装置与步骤 12

2.3 实验原料与产物的合成 13

2.3.1 对苯醌单缩酮的合成方法 13

2.3.2 产物的合成方法 13

2.4 化合物的表征方法 14

第三章 结果与讨论 15

3.1 实验条件优化与选择 15

3.2 反应适用范围研究 17

3.4 化合物的光谱数据 18

第四章 结论与展望 21

参考文献 22

附录 代表性化合物核磁共振图谱 25

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