Novel Method for Biomimetic Synthesis of Cyclohexyl Ketone Compounds

Chem. J. Chinese Universities

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Novel Method for Biomimetic Synthesis of Cyclohexyl Ketone Compounds

LI Jian-Li, YIN Wen-Ting, ZHANG Jin, GUO Yuan, WU Xiang-Long, BAI Yin-Juan, SHI Zhen*

Department of Chemistry, Northwest University, Xi′ an 710069, China

Received:2007-03-06 Revised:1900-01-01 Online:2008-01-10 Published:2008-01-10
Contact: SHI Zhen

Abstract

Abstract: The tetrahydrofolate coenzyme is the methyl source of the methylation for many materials (including the DNA and RNA) in the living body to transfer one carbon unit for the biosynthesis and metabolism. On the basis of the one-carbon unit transfer reaction of tetrahydrofolate coenzymes, six cyclohexyl ketone compounds were synthesized successfully with benzimidazolium salt as the tetrahydrofolate coenzyme model at formic acid oxidation level and Grignard reagent as a nucleophile to which one carbon unit was transferred via addition-hydrolysis reaction. Their structures were characterized by elemental analysis, ¹H NMR, IR and MS spectra. A novel method for the convenient biomimetic synthesis of cyclohexyl ketone compounds was provi-ded. The reaction mechanism and the effects of reaction conditions on the yield were investigated.

Key words: Cyclohexyl ketone compound, Tertrahydrofolate coenzyme model, Benzimidazolium salt, Grignard reagent, Biomimetic synthesis

CLC Number:

O625.42

TrendMD:

LI Jian-Li, YIN Wen-Ting, ZHANG Jin, GUO Yuan, WU Xiang-Long, BAI Yin-Juan, SHI Zhen*. Novel Method for Biomimetic Synthesis of Cyclohexyl Ketone Compounds[J]. Chem. J. Chinese Universities, doi: .

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Novel Method for Biomimetic Synthesis of Cyclohexyl Ketone Compounds

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