α-烯酰基环丁烯酮的合成及其应用研究

发布时间：2018-04-07 16:36

本文选题：α-烯酰基环丁烯酮　切入点：3-氨基环丁烯酮　出处：《东北师范大学》2017年硕士论文

【摘要】：环丁烯酮这类重要的小环化合物存在于药物活性分子或多种天然产物的结构中。因其高选择性开环反应的特点,该类化合物可作为一类重要的有机合成切块,广泛应用于生物活性大分子和天然产物的合成中。因此,环丁烯酮衍生物因其生物活性及很高的反应活性引起人们的高度关注。在该研究领域中,各种官能化的环丁烯酮的合成及其应用研究已经广泛报道,但是,到目前为止,人们对α-烯酰基环丁烯酮的合成研究却很少。本论文在前期获得多种环丁烯酮类化合物的基础上,对α-烯酰基环丁烯酮类化合物的合成及其开环反应在合成中的应用进行了深入研究,研究成果如下:以简单易得的3-氨基-2-丙酰基环丁烯酮化合物为底物,在LDA的作用下,利用其亚甲基与醛进行连续的亲核加成以及缩合反应,成功的合成了一系列α-烯酰基环丁烯酮类化合物。在此基础上,利用Cu(OTf)2为催化剂,通过连续的开环反应,获得了一系列多取代内酯类化合物。以3-氨基环丁烯酮化合物为起始原料,在醋酸铜的催化作用下,利用其与丁炔二酸二甲酯进行连续的开环以及关环的多米诺成环反应,高效的制备了一系列的全取代吲哚类化合物。该反应不仅具有起始原料简单易得、操作简单、产率高等优点,而且创建了一种由简单起始原料一步构建全取代吲哚类化合物的新途径。
[Abstract]:Important small ring compounds such as cyclobutenone are found in the structures of drug-active molecules or natural products.Because of its highly selective ring-opening reaction, this kind of compounds can be widely used in the synthesis of bioactive macromolecules and natural products as a kind of important organic synthetic block.Therefore, cyclobutenone derivatives have attracted much attention because of their biological activity and high reaction activity.In this field, the synthesis and application of various functionalized cyclobutene ketones have been widely reported. However, so far, few studies have been done on the synthesis of 伪 -enyl cyclobutenylenones.In this paper, on the basis of obtaining many kinds of cyclobutenone compounds, the synthesis of 伪 -enyl cyclobutenone compounds and the application of ring-opening reaction in the synthesis of 伪 -alkenyl cyclobutene ketones have been studied.The results are as follows: the simple and easily obtained 3-amino-2-propionyl cyclobutenone compound was used as the substrate for the continuous nucleophilic addition and condensation of methylene with aldehydes under the action of LDA.A series of 伪-allyl cyclobutenone compounds were successfully synthesized.On this basis, a series of polysubstituted lactones were obtained by continuous ring-opening reaction using Cu(OTf)2 as catalyst.Using 3-aminocyclobutenone compound as the starting material and under the catalysis of copper acetate, the 3-aminocyclobutene ketone reacted with dimethyl butyronate to open the ring and close the ring to form dominoes.A series of completely substituted indole compounds were prepared efficiently.This reaction not only has the advantages of simple raw material, simple operation and high yield, but also creates a new way to construct completely substituted indole compounds from simple starting material.
【学位授予单位】：东北师范大学
【学位级别】：硕士
【学位授予年份】：2017
【分类号】：O624.42

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