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有机化学 ›› 2007, Vol. 27 ›› Issue (12): 1605-1608. 上一篇    下一篇

研究简报

辅酶Q10的合成

金文虎，金晶，冀亚飞*   

  1. (华东理工大学药学院 上海 200237)
  • 收稿日期:2007-03-26 修回日期:2007-05-29 发布日期:2007-12-04
  • 通讯作者: 冀亚飞

Synthesis of Coenzyme Q10

JIN Wen-Hu, JIN Jing, JI Ya-Fei*   

  1. (School of Pharmacy, East China University of Science and Technology, Shanghai 200237)
  • Received:2007-03-26 Revised:2007-05-29 Published:2007-12-04
  • Contact: JI Ya-Fei

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以2,3,4,5-四甲氧基甲苯为原料, 经溴化、生成格氏试剂后在碘化亚铜存在下与(E)-4-氯-2-甲基-1-苯磺酰基-2-丁烯缩合得到合成辅酶Q10的关键中间体6-(E-3'-甲基-4'-苯磺酰基-2'-丁烯基)-2,3,4,5-四甲氧基甲苯. 此中间体与茄尼基溴缩合、脱砜基化反应和氧化三步反应, 最终制得标题化合物辅酶Q10, 以2,3,4,5-四甲氧基甲苯计总收率达31.3%.

关键词: 2,3,4,5-四甲氧基甲苯, 茄尼醇, 硝酸铈铵, 辅酶Q10

2,3,4,5-Tetramethoxytoluene was brominated to prepare 6-bromo-2,3,4,5-tetramethoxytoluene whose Grignard reagent was condensed with (E)-4-cholro-2-methyl-1-phenylsulfonyl-2-butene in the presence of cuprous iodide to obtain the intermediate 6-(E-3'-methyl-4'-phenylsulfonyl-2'-butenyl)-2,3,4,5- tetramethoxytoluene, from which coenzyme Q10 was finally achieved via condensation with solanesyl bromide, desulfonylation and oxidation with an overall yield of 31.3% based on 2,3,4,5-tetramethoxytoluene.

Key words: solanesol, ammonium cerium(IV) nitrate, coenzyme Q10, 2,3,4,5-tetramethoxytoluene