文章摘要
基于α-叔碳-β,γ-不饱和醛的制备全合成番茄红素
Synthesis of Lycopene Based on Preparation of β,γ-Unsaturated Aldehyde with α-Tertiary Center
投稿时间:2019-07-19  修订日期:2019-09-11
DOI:
中文关键词: 番茄红素  α-叔碳-β,γ-不饱和醛  Wittig-Horner反应  食品化学品
英文关键词: lycopene  β,γ-unsaturated aldehyde with α-tertiary center  Wittig-Horner reaction  food chemicals
基金项目:广州市科技计划项目(201903010070)
作者单位E-mail
谭奇坤 暨南大学 281442519@qq.com 
陈果 暨南大学  
彭青霞 暨南大学  
张伟坚 广州市增城区疾病预防控制中心  
晏日安 暨南大学 yanrian813@163.com 
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中文摘要:
      将一种α-取代-α,β-不饱和醛的制备方法应用于番茄红素(Ⅵ)的全合成中,通过该方法以廉价的原料假性紫罗兰酮(Ⅰ)制备了2, 6, 10-三甲基-3, 5, 9-十一烷三烯-1-醛(Ⅱ),然后与四乙基亚甲基二磷酸酯(Ⅲ)经过Wittig-Horner反应得到关键中间体3, 7, 11-三甲基-1, 4, 6, 10-四烯十二烷基膦酸二乙酯(Ⅳ),最终和2, 7-二甲基-2, 4, 6-辛三烯-1, 8-二醛(Ⅴ)进行Wittig-Horner反应、转位异构合成全反式番茄红素。反应共经历3步线性反应,总产率为37.0%。最终产物的结构采用IR、HRMS和NMR进行确证。
英文摘要:
      Lycopene(Ⅵ) was synthesized via α,β-unsaturated aldehyde with α-tertiary center strategy. Firstly, Pseudoionone(Ⅰ), an inexpensive raw material, was adopted to synthesize 2, 6, 10-trimethylundeca-3, 5, 9-trienal (Ⅱ). Then the key intermediate, diethyl (3, 7, 11-trimethyldodeca-1, 4, 6, 10-tetraenyl) phosphonate(Ⅳ), was formed by Wittig-Horne reaction of the aldehyde II and tetraethyl methylenebis-phosphonate(Ⅲ). The final product, all-E lycopene, can be collected after Wittig-Horner reaction and isomers rearrangement of compound Ⅳ and 2, 7-dimethylocta-2, 4, 6-triene-1, 8-dial(Ⅴ). The synthesis of lycopene needed only 3 steps, with the yield of 37.0%. The structure of all-E lycopene was characterized by IR, HRMS and NMR techniques.
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