高等学校化学学报 ›› 2003, Vol. 24 ›› Issue (2): 265.

• 论文 • 上一篇    下一篇

烯基取代的甲酸态四氢叶酸辅酶模型的合成及其碳单元转移反应

王兰英, 胡志彪, 史真   

  1. 西北大学化学系, 西安 710069
  • 收稿日期:2001-12-27 出版日期:2003-02-24 发布日期:2003-02-24
  • 通讯作者: 王兰英(1962年出生),女,副教授,博士研究生,从事有机合成研究.E-mail:wanglany@yahoo.com.cn E-mail:wanglany@yahoo.com.cn
  • 基金资助:

    陕西省教委科研专项基金(批准号:98JK120,02JK060)资助

Synthesis and Carbon Unit Transfer Reactions of Ethenyl Substituted N5, N10-C+R-tetrahydrofolate Coenzymes

WANG Lan-Ying, HU Zhi-Biao, SHI Zhen   

  1. Department of Chemistry, Northwest University, Xi′an 710069, China
  • Received:2001-12-27 Online:2003-02-24 Published:2003-02-24

摘要: 以邻苯二胺和乙酸为原料,经3步反应合成了8种烃基乙烯基取代的苯并咪唑盐,其结构用元素分析,1HNMR,IR,MS和UV-Vis进行了表征,并以其作为取代的甲酸态四氢叶酸辅酶模型,同亲核试剂(格氏试剂)反应得到烃基乙烯基取代的一碳单元完全转移的产物α,β-不饱和酮,为α,β-不饱和酮的合成提供了一种简便的仿生合成新方法.

关键词: 四氢叶酸, 辅酶模型, 苯并咪唑盐, &alpha, &beta, -不饱和酮

Abstract: Eight 1,3-dimethyl-2-alkyl ethenyl substituted benzimidazolium salts which were used as the models of N5, N10-C+R-tetrahydrofolate(THF) coenzymes at formic acid oxidation level were synthesized by the reaction of o-phenylenediamine with acetic acid giving 2-methyl benzimidazole, and the consecutive reaction with methyl iodide and aldehydes. Their molecular structures were characterized by elemental analysis, 1HNMR, IR, MS and UV-Vis spectra. These model compounds can react with nucleophilic reagents(Grignard reagents) to give alkyl ethenyl substituted one carbon unit transfer products α,β-unsaturated ketones. A convenient biomimetic method for synthesis of α,β-unsaturated ketones was provided.

Key words: Tetrahydrofolate, Coenzyme model, Benzimidazolium salt, α,β-Unsaturated ketones

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