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    • 4. 发明申请
    • Method of Preparing 2,6,10-Trimethyl-1,1-Dialkoxy-3,5,9-Undecatriene Used as an Intermediate of Lycopene
    • 制备用作番茄红素中间体的2,6,10-三甲基-1,1-二烷氧基-3,5,9-十一碳三烯的方法
    • US20120316366A1
    • 2012-12-13
    • US13493971
    • 2012-06-11
    • PENGFEI ZHANGCHAO SHENRUNPU SHENWEI LIUCHUNLEI WU
    • PENGFEI ZHANGCHAO SHENRUNPU SHENWEI LIUCHUNLEI WU
    • C07C41/01
    • C07C41/48C07C43/303
    • The present invention describes a novel synthetic method for preparing the key intermediate 2,6,10-trimethyl-1,1-dialkoxy-3,5,9-undecatriene of lycopene. An existing synthetic method have some disadvantages that it is very difficult to gain the raw material dialkyl 4-methyl-5,5-diakoxy-1-pentene-1-phosphonate (10) because no effective synthetic method can be adopted, and furthermore the obtained target compound is composed of several cis/trans isomers. This invention relates to a process comprising a condensation step wherein a starting C10-phosphonate is changed to its carbanion completely at a temperature of −40˜30 under an atmosphere of a non-reactive gas in an organic solvent catalyzed by base, and then C4-dialkyl is added to undergo Wittig-Horner condensation. This invention affords all trans C14-acetal and this method is characterized with the advantages of simple procedure, easy access to raw material and low cost, which makes it has the value of industrial application.
    • 本发明描述了一种制备番茄红素关键中间体2,6,10-三甲基-1,1-二烷氧基-3,5,9-十一碳三烯的新型合成方法。 现有的合成方法有一些缺点,因为没有有效的合成方法,难以获得原料的4-甲基-5,5-二烷氧基-1-戊烯-1-膦酸二烷基酯(10),此外, 得到的目标化合物由几种顺式/反式异构体组成。 本发明涉及一种包括缩合步骤的方法,其中起始C10-膦酸酯在-40〜30℃的温度下在非反应性气体的气氛中在由碱催化的有机溶剂中完全变成其碳负离子,然后将C4 加入二烷基以进行Wittig-Horner冷凝。 本发明提供全反式C14-缩醛,该方法的特点是操作简单,易于获得原料,成本低廉,具有工业应用价值。