テルペン類の極性非プロトン溶媒を用いる酸化反応 (第6報) : 数種のセスキテルペン炭化水素の自動酸化生成物について

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Oxygen was blown into a mixture of β-elemene (1) and γ-elemene (2), α-selinene (3) and β-selinene (4) or α-humulene (5) in a polar aprotic solvent (DMAc or DMSO) for 516 h at 100120°C. Oxidation of (1) and (2) took place to give 3-isopropenyl-4-methyl-4-vinyl-1-cyclohexanone (6) and 1-acetyl-3-isopropenyl-4-methyl-4-vinylcyclohexane (7), while (3) and (4) yielded mainly 11-eudesmen-3-one (8), 2-acetyl-4a, 8-dimethyl-1, 2, 3, 4, 4a, 5, 6, 8a-octahydronaphthalene (9) and 2-acetyl-4a-methyl-8-methylenedecahydronaphthalene (10). A similar oxidation of (5) was found to afford two products; humulene epoxide-II (11) and humulenol-II (12). <BR>The compounds (9) and (10) are new sesquiterpenoids.
社団法人日本油化学会の論文