一种呋喃类倍半木脂素的合成研究

发布时间：2018-11-26 07:33

【摘要】：木脂素类化合物种类繁多,在自然界中分布广泛,具有多种生物活性,是许多中药的有效成分,但在植物中含量较低,提取困难,这些因素严重限制木脂素研究的进展,故木脂素类化合物的合成研究受到了越来越多的关注,有关木脂素合成的报道也越来越多。本文主要对木脂素的定义,分类,分离纯化,理化性质,合成研究现状等方面进行综述,同时,对两种呋喃类木脂素化合物的全合成路线和最佳反应条件进行实验研究,主要内容如下:第一部分,从木脂素的定义,命名,分离纯化,分类,生物活性,理化性质,合成研究等方面对木脂素进行系统的介绍,通过分析已报道的木脂素的合成路线和方法,提出了两种呋喃类木脂素化合物的全合成路线和方法。第二部分,介绍了两种呋喃类木脂素化合物的最佳合成路线,对2-甲基-(2E)-丁烯酸-(2S,3R,4R)-2-(3,4-二甲氧苯基)-4-(3,4-二甲氧苄基)-3-四氢呋喃甲酯进行合成时,是以廉价的藜芦醛为原料,经过Stobbe缩合反应,酯化反应,Aldol反应等构建木脂素骨架,再经过两步还原反应,酯化反应,最终得到目标产物。对木脂素3-(4-羟基-3-甲氧基苯基)-(2E)-丙烯酸-(2S,3R,4R)-2-(4-羟基-3,5-二甲氧苯基)-4-[(4-羟基-3,5-二甲氧苯基)甲基]-3-四氢呋喃甲酯进行合成时,是以廉价的丁香醛为原料,依次经过苄基保护反应,Stobbe缩合反应,酯化反应,羟醛缩合反应构建木脂素基本骨架,再经过还原反应,脱水反应,酯化反应,脱保护反应等最终得到目标化合物。第三部分,对实验中的各步反应进行讨论,通过筛选反应中的催化剂,溶剂,反应时间,反应温度,投料比等因素来确定最佳反应条件,从而确定整个实验的最佳反应路线。
[Abstract]:Lignans are widely distributed in nature and have a variety of biological activities. They are active components of many traditional Chinese medicines, but they are difficult to be extracted because of their low content in plants. These factors seriously limit the progress of lignin research. Therefore, more and more attention has been paid to the synthesis of lignans, and there are more and more reports on the synthesis of lignans. In this paper, the definition, classification, separation and purification, physicochemical properties and synthesis status of lignans were reviewed. At the same time, the synthesis routes and optimum reaction conditions of two kinds of furan lignans were studied experimentally. The main contents are as follows: in the first part, the definition, naming, separation and purification, classification, biological activity, physicochemical properties and synthesis of lignin are introduced systematically. Based on the analysis of the reported synthesis routes and methods of lignans, two total synthesis routes and methods of furan lignans were proposed. In the second part, the optimum synthetic routes of two furan lignans were introduced, and 2-methyl- (2e) -butenoic acid- (2Sf3R), 4R) -2- (3o 4- dimethoxyphenyl) -4- (3- 4- dimethoxybenzyl) -3- tetrahydrofuran methyl ester was synthesized from cheap resveratrol by Stobbe condensation and esterification. The lignin skeleton was constructed by Aldol reaction, then the target product was obtained by two step reduction reaction and esterification reaction. P-lignan 3- (4-hydroxy-3-methoxy phenyl)-(2e) -acrylic acid-(2Sn3R), p lignan 3- (4-hydroxy-3-methoxy phenyl)-(2e) -acrylic acid 4R) -2- (4- (4-hydroxy-3- (5-dimethoxyphenyl) -4- [(4-hydroxy-3-dimethoxyphenyl) methyl] -3-tetrahydrofuran methyl ester was synthesized from cheap eugenaldehyde, Through benzyl protection reaction, Stobbe condensation reaction, esterification reaction, hydroxaldehyde condensation reaction to form the basic skeleton of lignin, then through reduction reaction, dehydration reaction, esterification reaction, deprotection reaction and so on, the target compound was finally obtained. In the third part, the optimum reaction conditions are determined by screening the catalyst, solvent, reaction time, reaction temperature, feed ratio and so on, so as to determine the optimal reaction route of the whole experiment.
【学位授予单位】：青岛科技大学
【学位级别】：硕士
【学位授予年份】：2017
【分类号】：O636

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