本文選題：α-烯�；h(huán)丁烯酮　切入點：3-氨基環(huán)丁烯酮　出處：《東北師范大學》2017年碩士論文

【摘要】：環(huán)丁烯酮這類重要的小環(huán)化合物存在于藥物活性分子或多種天然產(chǎn)物的結構中。因其高選擇性開環(huán)反應的特點,該類化合物可作為一類重要的有機合成切塊,廣泛應用于生物活性大分子和天然產(chǎn)物的合成中。因此,環(huán)丁烯酮衍生物因其生物活性及很高的反應活性引起人們的高度關注。在該研究領域中,各種官能化的環(huán)丁烯酮的合成及其應用研究已經(jīng)廣泛報道,但是,到目前為止,人們對α-烯�；h(huán)丁烯酮的合成研究卻很少。本論文在前期獲得多種環(huán)丁烯酮類化合物的基礎上,對α-烯�；h(huán)丁烯酮類化合物的合成及其開環(huán)反應在合成中的應用進行了深入研究,研究成果如下:以簡單易得的3-氨基-2-丙�；h(huán)丁烯酮化合物為底物,在LDA的作用下,利用其亞甲基與醛進行連續(xù)的親核加成以及縮合反應,成功的合成了一系列α-烯�；h(huán)丁烯酮類化合物。在此基礎上,利用Cu(OTf)2為催化劑,通過連續(xù)的開環(huán)反應,獲得了一系列多取代內酯類化合物。以3-氨基環(huán)丁烯酮化合物為起始原料,在醋酸銅的催化作用下,利用其與丁炔二酸二甲酯進行連續(xù)的開環(huán)以及關環(huán)的多米諾成環(huán)反應,高效的制備了一系列的全取代吲哚類化合物。該反應不僅具有起始原料簡單易得、操作簡單、產(chǎn)率高等優(yōu)點,而且創(chuàng)建了一種由簡單起始原料一步構建全取代吲哚類化合物的新途徑。
[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 偽 -enyl cyclobutenylenones.In this paper, on the basis of obtaining many kinds of cyclobutenone compounds, the synthesis of 偽 -enyl cyclobutenone compounds and the application of ring-opening reaction in the synthesis of 偽 -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 偽-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.
【學位授予單位】：東北師范大學
【學位級別】：碩士
【學位授予年份】：2017
【分類號】：O624.42

【參考文獻】

相關博士學位論文 前1條

1 韓曉丹;環(huán)丁烯酮的開環(huán)反應在有機合成中的應用研究[D];東北師范大學;2013年

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本文編號：1719980