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摘要： 内酯化合物是天然产物和具有生理活性的物质中常见的一个重要组成部分，所以，一直以来人们都非常关心内酯化合物的合成与研究，内酯化合物不仅仅是天然产物的重要合成砌块，另一方面，内酯化合物是一些精细化工产品和医药中间体的合成原料。功能化的内酯基团的引入对于改善药品的生物活性也具有着重要的作用，与此同时，将氟原子或含氟基团引入到内酯化合物中，能提升和改变化合物的生理活性。本文设计新的反应路线来合成碘代α-二氟苯乙酮类含氟砌块，将其与不同的烯酸反应，制备含羰基偕二氟内酯化合物。优化反应条件，筛选出最适合的引发剂为偶氮二异丁腈（AIBN），并确定其含量为30%反应效果最佳;其次，对溶剂进行的了筛选，最终确定乙腈为最适合溶剂；最后，经过试验确定反应的最佳温度为70℃。30552
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毕业论文关键词： 有机氟化学；二氟亚甲基；内酯；合成方法
The application of iodine alpha two fluorobenzene acetophenone fluorinated building block in the synthesis of carbonyl compounds with two fluorine lactone
Abstract: Lactone compounds are natural products and has a important part of physiologically active substances in common, so has been the people are very concerned about the synthesis and research of lactone compounds, lactone compounds is not only important synthetic block of natural products, on the other hand, it can used to synthesize fine chemical products and pharmaceutical intermediates. Function of the lactone group is introduced for drugs to improve biological activity also has a important role, at the same time, the fluorine or fluorinated groups were introduced to the lactone compounds, can improve and change the physiological activity of the compounds. In this paper, the design of new route to synthesis of iodo alpha difluorobenzene acetophenones fluorinated building block, the acid reaction with different, preparation containing carbonyl gem difluoro lactone compounds. Optimization of reaction conditions, selected the most suitable initiators for azobisisobutyronitrile (AIBN) and determine its content is 30% reaction has the best effect; secondly, the solvent is selected, and ultimately determine the acetonitrile as the most suitable solvent. Finally, through the test to determine the response of the optimal temperature of 70℃ .
Keywords: Organic fluorine chemistry; Difluoromethylene unit; Lactone; Synthesis method
目录
目录 iv
1 前言 1
1.1 含氟化合物 1
1.2 含二氟亚甲基化合物 4
1.3 引入二氟亚甲基的方法 5
1.3.1 直接氟化法 5
1.3.2 含氟砌块法 6
1.3.3 自由基氟代反应 8
2 文献综述 9
2.1 内酯 9
2.2 含氟内酯的修饰 9
2.3 本课题的目的与意义 12
2.4 本课题的内容 12
3 实验操作 14
3.1 主要试剂及仪器 14
3.1.1 主要试剂 14
3.1.2 主要仪器 16
3.2 试验操作 16
3.2.1 含三氟甲基的烯醇式化合物的合成 16
3.2.2 二氟取代的三氟甲基偕二醇砌块的制备 17
3.2.3 碘代的二氟砌块的合成 18
3.2.4 目标内酯化合物的合成 18
4 试验讨论 21
4.1 碘代的二氟砌块与烯酸的自由基反应所需要的引发剂及其用量的筛选 21
4.2 碘代的二氟砌块与烯酸的自由基反应溶剂的筛选 21