1,2,3,6-Tetrahydro-6-(3,4-dimethoxyphenyl)-phthalic Acidおよび関連化合物のFriedel-Crafts反応について

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概要

• 論文の詳細を見る

• The previously assigned strocture, which has a indanone moiety, for the Friedel-Crafts cyclization product of 3-(3,4-dimethoxyphenyl)-1,2,3,6-tetrahydrophthalic acid (1) and its anhydride (14) should be revised to the tetralone (12) based on its spectral data and its chemical reactions. The methylenedioxy analogs (7 and 8) also gave the tetralone (10) by the same reaction. Oxidative decarboxylation of the dihydroderivative (13) of 12 with lead tetraacetate in benzene gave the acetate (17) and the phenyl derivative (16). The former was hydrolyzed to the alcohol (18) which was converted to the tosylate (19). Lithium aluminium hydride reduction of the tosylate gave the dimethoxyphenyl-cyclohexene (20) as a fragmentation product. When the oxidative decarboxylation was carried out in the presence of lithium chloride, a mixture of two stereoisomeric chlorides (22a, b) was obtained. Raney nickel reduction of the mixture gave the tetralone (23), whose infrared spectrum exhibited a carbonyl band at 1663 cm^<-1>. Furthermore, the synthetic sample of 6,7-dimethoxy-1,2,3,4,4a.9a-hexahydrofluoren-9-one (15), derived from 3,4-dimethoxybenzoyl chloride and cyclohexane, was not identical with the reduction product of the chlorides (22a. b), confirming the structures of the Friedel-Crafts cyclization products of the tetrahydrophthalic acid (1) and its analogs (2,7,8,and 14).

• 公益社団法人日本薬学会の論文
• 1975-08-25

著者

• 入江 寛

  Faculty Of Pharmaceutical Sciences Kyoto University

• 上尾 庄次郎

  京都大学薬学部

• 杉田 稔

  京都大学薬学部

• 入江 寛

  京都大学薬学部

• 西谷 康宏

  京都大学薬学部

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