【摘要】：ε-胡蘿卜素是天然類胡蘿卜素家族中的一員,是一種抗氧化劑,可以中和體內(nèi)的過氧化自由基,起到了延緩衰老的作用,還能維持和促進免疫功能。因其獨特的抗氧化保健作用,是目前類胡蘿卜素類物質(zhì)研究中的熱點之一。本論文設(shè)計并成功開發(fā)了一條ε-胡蘿卜素的合成新路線:(1)以α-環(huán)檸檬醛與C4膦酸酯經(jīng)Wittig-Horner縮合反應(yīng)得到化合物C14烯醇醚,產(chǎn)品純度97.6%,收率達68.3%;再水解得到中間體C14醛,產(chǎn)品純度98.1%,收率為71.7%。其中C14烯醇醚為新化合物,該合成方法已經(jīng)申請中國發(fā)明專利(CN104418713A)。(2)C14醛再與偕二膦酸酯經(jīng)Wittig-Horner縮合反應(yīng)得到關(guān)鍵中間體C15膦酸酯產(chǎn)品含量為94.3%,收率達90.1%,其中C15膦酸酯為新化合物,該合成方法已經(jīng)申請中國發(fā)明專利(CN104418885A)(3)最后,C15膦酸酯與C10雙醛經(jīng)Wittig-Horner反應(yīng)合成得到ε-胡蘿卜素,產(chǎn)品純度96.8%,收率74.5%。該合成方法已經(jīng)申請中國發(fā)明專利(CN104418885A),發(fā)表論文一篇(Practical Synthesis ofε-Carotene.synthesis-stuttgart,2015,47,481 484)。通過1H-NMR,13C-NMR,DEPT135和GC-MS等對涉及的中間體和產(chǎn)物進行了結(jié)構(gòu)鑒定,該工藝路線主要采用Wittig-Horner縮合技術(shù),僅需4步反應(yīng)步驟短,操作簡單,原料易得,條件溫和,副反應(yīng)少,對ε-胡蘿卜素及相關(guān)中間體的合成具有重要的意義。
[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 偽 -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.
【學(xué)位授予單位】：紹興文理學(xué)院
【學(xué)位級別】：碩士
【學(xué)位授予年份】：2017
【分類號】：O629.4

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