【作者】 马玉慧；

【导师】 王芒；

【作者基本信息】 东北师范大学 ， 有机化学， 2009， 硕士

【摘要】 官能化二硫缩烯酮是一类重要的有机合成中间体。自从1910年由Kelber首次合成出α-苯甲酰基二甲硫缩烯酮以来,经过近百年的发展已经成为有机合成化学的研究热点之一。官能团的多样性这一结构特点和烷硫基的空间电子效应赋予了该类化合物化学反应的多样性。利用该中间体可以合成许多具有特殊结构的化合物,广泛地应用于有机合成和天然产物的合成中。碳碳键形成和官能团的转化反应是构建有机分子骨架最重要、最基本的反应。多组分化学反应具有操作简便、资源利用率高以及高原子经济性等特点,是一类重要的有机化学反应,在新药设计与合成、组合化学和天然产物合成中具有广泛的应用。结合碳碳键形成反应和多组分反应研究的重要性,本论文拟以α-烯酰基基二硫缩烯酮为研究对象,着重研究了这类化合物和各种醛及活泼亚甲基类化合物的三组分反应.我的研究工作主要有以下几方面:1.研究α-烯酰基二硫缩烯酮、甲醛和活泼亚甲基化合物一锅煮反应形成多取代环己酮类化合物的可行性。2.依次变换各种α-烯酰基基二硫缩烯酮、醛类化合物及各种活泼亚甲基化合物。3.多取代环己酮合成不对称芳基化合物的应用研究。4.摸索最佳反应条件。5.研究反应机理。本文合成了36个未见文献报道的新化合物,并对其进行了IR、¹H-NMR、¹³C-NMR等数据表征。更多还原

【Abstract】 Functionalized ketenedithioacetals are a kind of versatile intermediates in organic synthesis. Since Kelber first synthesized in 1910,α-oxo ketene-（S,S）-acetals chemistry has become a hot spot in organic chemistry research through the development of about one hundred years. It can be used in many reactions for their functional group multiplicity and special stereoelectronic effect from the alkylthio functionalities. It can construct many compounds with special structures and can be applied in organic synthesis and the composition of natural products.The carbon-carbon bond formation and the functional group transformations are most fundamental reactions for the construction of a molecular framework and hence represent a forefront of research in organic chemistry. Multicomponent reactions （MCRs） have been refined in recent years into powerful and useful tool in synthetic chemistry and attract increasing attention due to the fact that complex molecules and drugs can be prepared from cheap and easily available starting materials. This reaction covers simple operation, high resource utilization and high atom economy, etc. And it can be applied in the design, synthesis of new drugs, and compounds with special structures.In connection with the importance of carbon-carbon bond formation and multicomponent reactions, we will investigate the three components reaction ofα-alkenoyl ketene S,S-acetals, different aldehydes and active methylene compounds.My research includes the following five aspects:1、Explore the possibility of the three component reaction of readily availableα-alkenoyl ketene S,S-acetals with aldehydes and active methylene compounds to give various polyfunctionalized cyclohexanones.2、Variation of theα-Alkenoyl Ketene S,S-acetals, aldehydes and active methylene compounds in sequence.3、Application of polyfunctionalized cyclohexanones in the synthesis of unsymmetrical biaryls.4、Explore the optimization of the reaction conditions.5、Study the possible mechanism.Thirty-six new compounds were synthesized and characterized by IR, Mass and NMR (¹H, ¹³C) spectrum in this thesis.更多还原