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

Synthesis and Carbon Unit Transfer Reactions of Ethenyl Substituted N^5, N^(10)-C^+R-tetrahydrofolate Coenzymes

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 ,1 H NMR,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 .

Eight 1,3-dimethyl-2-alkyl ethenyl substituted benzimidazolium salts which were used as the models of N 5, N 10-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, 1H NMR, 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.