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二十四种作为麝香酮及类似大环酮重要中间体的长链二酮的仿生合成
引用本文:郭媛,a,b 陈康裕a 李剑利a 史真a.二十四种作为麝香酮及类似大环酮重要中间体的长链二酮的仿生合成[J].中国化学,2008,26(12):2249-2255.
作者姓名:郭媛  a  b 陈康裕a 李剑利a 史真a
作者单位:(1.西北大学化学系,西安 710069) ;(2.第四军医大学基础部生物化学与分子生物学教研室,西安 710032) ;
摘    要:烷基取代的大环酮(例如,名贵香料麝香酮)是珍贵的香料,天然来源稀少,它的人工合成一直是有机合成中的一个研究热点和难点。在本文中,受四氢叶酸辅酶的一碳单元转移反应的启发,作者以双苯并咪唑盐作为四氢叶酸辅酶模型,利用格利雅试剂与双苯并咪唑盐的加成-水解反应,成功合成了二十四种作为麝香酮及类似大环酮重要前体的长链二酮,同时,提供了一种麝香酮及类似大环酮的仿生合成新方法。

关 键 词:麝香酮  烷基取代的大环酮、双苯并咪唑盐  长链二酮  仿生合成
收稿时间:2008-4-28
修稿时间:2008-7-6

Biomimetic Synthesis of Twenty‐four Long‐chained Diketones as Precursors for Muscone and Further Macrocyclic Ketones
Yuan GUO,Kang‐Yu CHEN,Jian‐Li LI,Zhen SHI.Biomimetic Synthesis of Twenty‐four Long‐chained Diketones as Precursors for Muscone and Further Macrocyclic Ketones[J].Chinese Journal of Chemistry,2008,26(12):2249-2255.
Authors:Yuan GUO  Kang‐Yu CHEN  Jian‐Li LI  Zhen SHI
Institution:1. Key Laboratory of Synthetic and Natural Functional Molecule Chemistry (Ministry of Education), Department of Chemistry, Northwest University, Xi'an, Shaanxi 710069, China;2. State Key Laboratory of Cancer Biology, Institute of Molecular Biology, Fourth Military Medical University, Xi'an, Shaanxi 710032, China;3. Tel.: 0086‐029‐81739198;4. Fax: 0086‐029‐88303606
Abstract:The one‐carbon unit transfer reaction of tetrahydrofolate coenzyme was initiated. Bisbenzimidazolium salts were used as a tetrahydrofolate coenzyme model, and thus the biomimetic synthesis of twenty‐four acyclic diketones as precursors for macrocyclic ketones was successfully accomplished by using the addition‐hydrolysis reaction of the bisbenzimidazolium salts with alkyl magnesium halide, wherein six diketones have not been reported in literature. Accordingly, a short route to muscone analogues was provided.
Keywords:muscone  alkyl‐substituted macrocyclic ketone  bisbenzimidazolium salt  acyclic diketone  biomimetic synthesis
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