摘  要：4-氟环己酮是一种比较重要的含氟化合物，广泛用于医药中间体的合成。目前合成4-氟环己酮的方法报道很少，文献中报道的合成路线原料价格高，收益率低，无法满足工业生产，不具开发价值。我们从设计角度独创了一条合成路线，主要包括以下内容：通过有机碱的加入，使得氟化剂与1,4-环己二酮单乙二醇缩酮反应生成8-氟-1,4-二氧杂螺[4.5]癸-7-烯，在钯碳催化剂作用下通过氢气还原为8-氟-1,4-二氧杂螺[4.5]癸烷，并加酸脱保护得到4-氟环己酮。本论文通过研究不同反应条件对产率的影响，得出最佳工艺条件。该合成方法使用的原料来源广泛、价格低廉 ，每一步反应都能最大化得到纯度较高的中间体，最终产物的纯度更是高达94%，经济效益明显，对环境污染较小，特别适合工业化大规模应用和推广。

关键词：4-氟环己酮；氟化剂；工艺研究；制备

Study on Preparation of 4-Fluorocyclohexanone

Abstract：4-Fluorocyclohexanone is an important fluorine-containing compound and is widely used in the synthesis of pharmaceutical intermediates. At present, there are few reports on the synthesis of 4-fluorocyclohexanone. The synthetic routes reported in the literature have high raw material prices and low yields, and they cannot meet industrial production and have no development value.We have created a synthetic route from the perspective of design, mainly including the following: through the addition of organic bases, the fluorinating agent reacts with 1,4-cyclohexanedione monoethylene ketal to form 8-fluoro-1,4-mercapto. Dioxaspiro[4.5]dec-7-ene is reduced to 8-fluoro-1,4-dioxaspiro[4.5]decane by hydrogen gas under the action of a palladium carbon catalyst and deprotected by acid to give 4-fluoro Cyclohexanone.In this dissertation, the influence of different reaction conditions on the yield was studied and the best process conditions were obtained. The synthesis method uses a wide range of sources of raw materials, low cost, can maximize the purity of the intermediates for each step of the reaction, the purity of the final product is as high as 94%, significant economic benefits, less environmental pollution, especially suitable for industrialization Large-scale application and promotion.

Key words: 4-fluorocyclohexanone; fluorinating agent; process research; preparation

目录

第一章  前言 1

1.1 研究背景 1

1.2 有机氟化学的发展 1

1.3 有机氟化学的应用 2

1.3.1 在医药方面的应用 2

1.3.2 在农药方面的应用 2

1.3.3在染料方面的应用 2

1.3.4 在有机氟中间体方面的应用 2

1.4 DAST机理与应用 2

1.4.1 DAST的机理 2

1.4.2 DAST的应用 3

1.5 4-氟环己酮制备及发展 4

1.6 研究内容 6

1.7研究意义 6

第二章  实验部分 7

2.1以有机碱种类合成4-氟环己酮的研究 7

2.1.1主要研究内容 7

2.1.2  试剂与仪器 7

2.1.3  实验内容 8

2.1.4结果与讨论