Chemistry of 2-Methoxy-2,5-cyclohexadienone. V. Photochemical Rearrangement and Oxidation of 2-Methoxy-4-methyl-4-phenyl-2-cyclohexenone and 2-Methoxy-4-methyl-4-phenyl-2,5-eyclohexadienone(Organic,Chemical)

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概要

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• A methanolic solution of 2-methoxy-4-methyl-4-phenyl-2-cyclohexenone (I) was irradiated with a IOOW mercury lamp to give 4-methyJ-4-phenyl-2-cyclohexenone (III) and l-methoxy-5-methyl-6-phenylbicyclo[3.1.0]hexan-2-one (IV). When a benzene solution of I was irradiated, only IV was obtained. On the other hand, 2-methoxy-4-methyl-4-phenyl-2,5-cyclohexadienone (II) gave 2,2-dimethoxy-6-methyl-6-phenylbicyclo[3.1.0]hexan-3-one (V) and 6,6-dimethoxy-5-methyl-5- phenyl-3-cyclohexenone (VI) on photoirradiation in methanol. In benzene, 6-methoxy-6-methyl-5- phenyl-2,4-cyclohexadienone (XI) was obtained. Compound II was treated with m-chloroperbenzoic acid in a bilayer system of methylene chloride-aqueous disodium orthophosphate at room temperature to give 5,6-epoxy-6-methoxy-4-methyl-4-phenyl-2-cyclohexenone (XVI) and its stereoisomer (XVI'). 5,6-Epoxy-2-methoxy-4-methyl-4-phenyl-2-cyclohexenone (XVIII) was obtained by treatment of II with hydrogen peroxide in a basic medium. 2,3:5,6-Diepoxy-6-methoxy-4-methyl-4-phenyl-6-hexanolide (XVII) rather than the expected diepoxide (XII) was obtained by the alternative oxidation of XVI or XVIII.

• 社団法人日本薬学会の論文
• 1987-07-25

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

• 野田 浩子

  Faculty of Pharmaceutical Sciences, Toyama Medical & Pharmaceutical University

• 的場 勝英

  Faculty Of Pharmaceutical Sciences Toyama Medical & Pharmaceutical University

• 的場 勝英

  Faculty Of Pharmaceutical Sciences Osaka University

• 野田 浩子

  Faculty Of Pharmaceutical Sciences Toyama Medical & Pharmaceutical University

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