Chemistry of 2-Methoxy-2,5-cyclohexadienones. II. Oxidation of 2-Methoxy-4,4-dimethyl-2,5-cyclohexadienone

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概要

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• 2-Methoxy-4,4-dimethyl-2-cyclohexenone (II) afforded 5,6-epoxy-6-methoxy-4,4-dimethyl-6-hexanolide (III) upon reaction with m-chloroperbenzoic acid in 1,1,1-trichloroethane. On the other hand, the treatment of II with the same reagent in an aqueous disodium orthophosphate-methylene chloride system at 4℃ gave 2,3-epoxy-2-methoxy-4,4-dimethylcyclohexanone (V), which could be converted to methyl 2-hydroxy-1-methoxy-3,3-dimethylcyclopentanecarboxylate (VI). 2-Methoxy-4,4-dimethyl-2,5-cyclohexadienone (I) afforded 5,6-epoxy-2-methoxy-4,4-dimethyl-2-cyclohexenone (VIII) upon reaction with hydrogen peroxide in a basic medium. The reaction of I with m-chloroperbenzoic acid at room temperature gave 5,6-epoxy-6-methoxy-4,4-dimethyl-2-cyclohexenone (X). Neither VIII nor X gave the expected 2,3,5,6-diepoxy-2-methoxy-4,4-dimethylcyclohexanone (VII), but afforded 2,3,5,6-diepoxy-6-methoxy-4,4-dimethyl-6-hexanolide (IX).

• 社団法人日本薬学会の論文
• 1984-07-25

著者

• 山崎 高應

  Faculty of Pharmaceutical Sciences, University of Toyama

• 的場 勝英

  Faculty of Pharmaceutical Sciences, University of Toyama

• 山崎 高広

  富山医科薬科大学

• 山崎 高應

  Faculty Of Pharmaceutical Sciences Toyama Medical And Pharmaceutical University

• 苅部 則夫

  Faculty of Pharmaceutical Sciences, Toyama Medical and Pharmaceutical University

• 的場 勝英

  Faculty Of Pharmaceutical Sciences Toyama Medical & Pharmaceutical University

• 的場 勝英

  Faculty Of Pharmaceutical Sciences Osaka University

• 苅部 則夫

  Faculty Of Pharmaceutical Sciences Toyama Medical And Pharmaceutical University

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