论文总字数：32948字

摘 要

在有机联烯类化学领域中，目前最新进展是在生物学和药物方向进行新化合物的开发。而在这些领域中，联烯化合物的应用已经变得越来越重要，并且各类联烯化合物已经被发现和合成，例如联烯卤素化合物、联烯醇、联烯胺、联烯醛、联烯酸、联烯酯、联烯酮、联烯酰胺、联烯砜、联烯亚砜和联烯腈等等。由于联烯是由两个碳碳双键连接而成，两个π键轨道相互垂直。并且，其中任意一个都分别可以与直接相连的π键体系共轭，因此具有一些独特的性质，使其在合成化学的应用越来越广泛。目前相关的研究主要集中在两方面。其一是利用联烯通过环化反应合成各类五元环、六元环以及杂环化合物。其二是通过亲核试剂对联烯的亲核加成制备各种烯烃衍生物和大环化合物。而目前对合成联烯化合物的研究也取得了一定的进展。本次课题研究的是利用醇类化合物通过与溴乙酸脱水酯化合成相应的溴代酯类化合物，并利用witting反应制备获得各类磷叶立德试剂，最后通过和乙酰氯在碱性条件下反应并以中等偏上的产率获得不同结构的联烯酸酯化合物。起初我们通过上述方法进行文献重复，制备联烯酸酯化合物；此后按照这种合成方法进行烷基醇的拓展，进一步制备这类化合物。但是拓展烷基醇制备联烯酸酯化合物的反应效果并没有文献重复中的好，有待进一步研究。此外，本研究也对合成的联烯酸酯类化合物进行表征，并记录实验数据。同时对实验结果进行讨论和分析，其中值得一提的是，该合成策略对具有天然化合物结构的醇类化合物也有很好的兼容性，使其在相关领域的应用会更加广泛。

关键词：联烯化学、环化反应、选择性加成、联烯合成、联烯酸酯

Synthesis and Application of the Diene

Abstract

The latest development in the field of organic alkene chemistry is devoted to the development of new compounds in the field of biology and medicine. In the chemistry of organic dienes, the application of dienes is becoming more and more important. And various types of allene compounds have been discovered and synthesized, for example, biene halogen compounds, bienolol, bienylamine, bienal, bienic acid, bienyl ester, bienone, bienamide, bienolsulfone, diene sulfoxide and bienile, etc. Since the structure of allene contain two carbon-carbon double bonds, and the two π system are perpendicular to each other. Any one of them will also be conjugate to the directly connected π system, which makes it have some unique properties and has found wide applications in the synthesis. At present, relevant research mainly focuses on cyclization reaction and selective addition reaction, which could participate in these reactions smoothly and delivering a series of cyclic compounds and olefin derivatives. On the other hand, research on the synthesis of allene compounds has also made great progress. In this study, the corresponding bromoester compounds were synthesized by esterification of bromoacetic acid and alcohol compounds. Then the corresponding bromoester compounds were used to prepare various kinds of phosphorus ylide reagents. And different structural allenoate compounds were finally obtained the by using phosphorus ylide reagents reacted with acetyl chloride under basic conditions. At first, we repeated the literature to prepare bienyl ester compounds by the above methods, and then extended alkyl alcohols according to this method to further prepare these compounds. However, the reaction effect of expanding alkyl alcohol to bienate ester compounds is not as good as that of literature repetition, which needs to be further studied. In addition, the allenoate synthesized in this study were characterized and the experimental data were also recorded. According to the results, we found that this strategy is also compatible with natural alcohol, which will make it find more applications in related fields.

Key words: Alkene chemistry, Cyclization, Selective addition, Synthesis of allene, Allenoate

目 录

摘要 Ⅰ

ABSTRACT i

第一章 文献综述 1

1.1引言 1

1.2联烯类化合物的应用 1

1.3联烯类化合物的合成 10

第二章 实验 12

2.1前言 12

2.2 实验部分 12

2.3香芹醇与邻乙烯苯甲醇的制备 15

2.4实验结果与讨论 16

2.5本章涉及的部分化合物表征 18

第三章 结论与展望 22

3.1 结论 22

3.2 展望 22

附录 23

参考文献 30

致谢 34

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