ε-胡萝卜素的全合成研究

发布时间：2018-10-14 13:59

【摘要】：ε-胡萝卜素是天然类胡萝卜素家族中的一员,是一种抗氧化剂,可以中和体内的过氧化自由基,起到了延缓衰老的作用,还能维持和促进免疫功能。因其独特的抗氧化保健作用,是目前类胡萝卜素类物质研究中的热点之一。本论文设计并成功开发了一条ε-胡萝卜素的合成新路线:(1)以α-环柠檬醛与C4膦酸酯经Wittig-Horner缩合反应得到化合物C14烯醇醚,产品纯度97.6%,收率达68.3%;再水解得到中间体C14醛,产品纯度98.1%,收率为71.7%。其中C14烯醇醚为新化合物,该合成方法已经申请中国发明专利(CN104418713A)。(2)C14醛再与偕二膦酸酯经Wittig-Horner缩合反应得到关键中间体C15膦酸酯产品含量为94.3%,收率达90.1%,其中C15膦酸酯为新化合物,该合成方法已经申请中国发明专利(CN104418885A)(3)最后,C15膦酸酯与C10双醛经Wittig-Horner反应合成得到ε-胡萝卜素,产品纯度96.8%,收率74.5%。该合成方法已经申请中国发明专利(CN104418885A),发表论文一篇(Practical Synthesis ofε-Carotene.synthesis-stuttgart,2015,47,481 484)。通过1H-NMR,13C-NMR,DEPT135和GC-MS等对涉及的中间体和产物进行了结构鉴定,该工艺路线主要采用Wittig-Horner缩合技术,仅需4步反应步骤短,操作简单,原料易得,条件温和,副反应少,对ε-胡萝卜素及相关中间体的合成具有重要的意义。
[Abstract]:蔚 -carotene is a member of the natural carotenoid family, it is an antioxidant, can neutralize the peroxidation free radicals in the body, play the role of anti-aging, but also maintain and promote the immune function. Because of its unique antioxidant health care, it is one of the hot spots in the research of carotenoids. In this paper, a new route for the synthesis of 蔚 -carotene was designed and successfully developed: (1) C14 enol ether was synthesized by Wittig-Horner condensation of 伪 -cyclocitral and C4 phosphonate, the purity of the product was 97.66.The yield was 68.3%, and the intermediate C14 aldehyde was obtained by hydrolysis. The purity of the product was 98.1 and the yield was 71.7%. The synthesis method has been applied for Chinese invention patent (CN104418713A). (_ 2) C _ 14 aldehydes and then condensed with amidodiphosphonate through Wittig-Horner condensation to obtain the key intermediate C _ 15 phosphonate in 94.3% yield of 90.1%, in which C _ 15 phosphonic acid ester is a new compound. The synthetic method has been applied for Chinese invention patent (CN104418885A) (3). Finally, the synthesis of 蔚 -carotene by Wittig-Horner reaction of C15 phosphonate and C10 dialdehyde was carried out. The purity of the product was 96.8. the yield was 74.5. The synthetic method has been patented in China (CN104418885A) and published a (Practical Synthesis of 蔚-Carotene.synthesis-stuttgart,2015,47481 484). The structures of the intermediates and products were identified by 1H-NMR-13C-NMR-DEPT135 and GC-MS. The Wittig-Horner condensation technology was mainly used in this process. The reaction steps were only four steps short, the operation was simple, the raw materials were easily obtained, the conditions were mild, and the side reactions were few. It is of great significance for the synthesis of 蔚-carotene and related intermediates.
【学位授予单位】：绍兴文理学院
【学位级别】：硕士
【学位授予年份】：2017
【分类号】：O629.4

【参考文献】