利用两相Friedel-Crafts反应合成质体醌Plastoquinone-9
Synthesis of plastoquinone-9 by two-phase Friedel-Crafts reaction
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摘要: 以2,3-二甲基苯胺经硅胶受载氧化剂Na2CrO7-H2SO4氧化、NaBH4还原生成的2,3-二甲基-1,4苯二酚作为质体醌的合成母体,在CH3NO2-正己烷两相反应体系中,43~45℃及BF3·Et2O催化下与从烟浸膏精制的高纯茄尼醇发生Friedel-Crafts反应合成质体醌Plastoquinone-9的氢醌,再经催化量的FeCl3·6H2O存在下的空气氧化,以满意的收率及选择性合成了Plastoquinone-9.Abstract: With two-phase reactive system of CH3NO2/n-hexane,the hydroquinone of plastoquinone-9 was prepared at 43—45℃ by BF3·Et2O catalyzed Friedel-Crafts alkylation reaction of 2,3-dimethyl-1,4-hydroquinone,which was synthesized from 2,3-dimethylaniline via oxidation,reduction,and pure solanesol isolated from extractum tobacco.Then through a green oxidation of hydroquinone with air and a catalytic amount of FeCl3·6H2O,plastoquinone-9 was synthesized in good yield and high selectivity.