A Facile Synthesis of 1,4-Benzoquinones Having a Hydroxyalkyl Side Chain

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概要

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• 6-(ω-Hydroxyalkyl)-2,3-dimethoxy-5-methyl-1,4-benzoquinones (3) and 6-(ω-acetoxyalkyl)-2,3-dimethoxy-5-methyl-1,4-benzoquinones (26) having various carbon numbers (n) of the side chain were synthesized by the Friedel-Crafts coupling of 3,4,5-trimethoxytoluene (4) and ω-acetoxyalkanoyl chlorides (5) as a key step. The Fremy's salt oxidation or the salcomine-catalyzed oxidation of 6-(ω-hydroxyalkyl)-2,3-dimethoxy-5-methylphenols (25) and their acetates (24), the key intermediates of the process, gave rise to 3 and 26,respectively, in good yields. The described method provides a good yield of the 1,4-benzoquinones and is suitable for the synthesis of other quinonyl analogs. The effect on lipid peroxidation in canine brain homogenate of the 1,4-benzoquinones (3) having various carbon numbers (n) of the side chain was studied. Among the compounds tested, 3 having a carbon number in the range of n=9-13 showed rather strong antioxidant activity.

• 公益社団法人日本薬学会の論文
• 1985-10-25

著者

• 後藤 義一

  Central Research Division, Takeda Chemical Industries, Ltd.

• 奥谷 哲也

  Central Research Division, Takeda Chemical Ind., Ltd.,

• 今田 伊助

  Central Research Division, Takeda Chemical Industries, Ltd.

• 後藤 義一

  Pharmaceutical Research Laboratories I Pharmaceutical Research Division Takeda Chemical Industries L

• 岡本 加世子

  Central Research Division, Takeda Chemical Industries, Ltd.

• 奥谷 哲也

  Central Research Division Takeda Chemical Industries Ltd.

• 今田 伊助

  Central Reseach Division Takeda Chemical Industries Ltd.

• 岡本 加世子

  Central Reseach Division Takeda Chemical Industries Ltd.

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