（E）-4-[2-(3,4-二氢-4,4-二甲基-2H-1-苯并吡喃-6-基)-1-丙烯基]苯甲酸乙酯潜在代谢产物的合成
Synthesis of potential metabolites of ethyl (E)-4-[2-(3,4-dihydro-4,4-dimethyl-2H-1-benzopyran-6-yl)-1-propenyl] benzoate.
作者信息
Sunthankar P S, Berlin K D, Nelson E C, Thorne R L, Geno P W, Archer J C, Rolf L L, Bartels K E
机构信息
Department of Chemistry, Oklahoma State University, Stillwater 74078.
出版信息
J Pharm Sci. 1993 May;82(5):543-5. doi: 10.1002/jps.2600820522.
Potential metabolites of ethyl (E)-4-[2-(3,4-dihydro-4,4-dimethyl-2H-1-benzopyran-6-yl)-1-propenyl] benzoate were synthesized. The new compounds include ethyl 3-[3,4-dihydro-4,4-dimethyl-2H-1-benzopyran-6-yl]crotonate, 3-[3,4-dihydro-4,4-dimethyl-1H-1-benzopyran-6-yl]crotonic acid, 3,4-dihydro-4,4-dimethyl-2H-1-benzopyran-6-carboxylic acid, 4-[3,4-dihydro-4,4-dimethyl-2H-1-benzopyran-6-yl]delta 2-butenolide, ethyl (E)-4-[3,4-dihydro-4,4-dimethyl-2H-1-benzopyran-6-yl)-3-hydroxy-1- propenyl]benzoate, ethyl (E)-4-[2-(3,4-dihydro-4,4-dimethyl-2H-1-benzopyran-6-yl)-2-propenal] benzoate, and ethyl (E)-4-[2-(3,4-dihydro-4,4-dimethyl-2H-1-benzopyran-6-yl)-2-propenoic+ ++ acid]benzoate. Stereospecific oxidizing reagents and/or conditions were developed for these sensitive systems and include the use of SeO2, Clorox bleach, activated MnO2, and NaClO2 in the presence of resorcinol as a chlorine scavenger.
合成了（E）-4-[2-(3,4-二氢-4,4-二甲基-2H-1-苯并吡喃-6-基)-1-丙烯基]苯甲酸乙酯的潜在代谢产物。新化合物包括3-[3,4-二氢-4,4-二甲基-2H-1-苯并吡喃-6-基]巴豆酸乙酯、3-[3,4-二氢-4,4-二甲基-1H-1-苯并吡喃-6-基]巴豆酸、3,4-二氢-4,4-二甲基-2H-1-苯并吡喃-6-羧酸、4-[3,4-二氢-4,4-二甲基-2H-1-苯并吡喃-6-基]δ2-丁烯内酯、（E）-4-[3,4-二氢-4,4-二甲基-2H-1-苯并吡喃-6-基)-3-羟基-1-丙烯基]苯甲酸乙酯、（E）-4-[2-(3,4-二氢-4,4-二甲基-2H-1-苯并吡喃-6-基)-2-丙烯醛]苯甲酸乙酯和（E）-4-[2-(3,4-二氢-4,4-二甲基-2H-1-苯并吡喃-6-基)-2-丙烯酸]苯甲酸乙酯。针对这些敏感体系开发了立体选择性氧化试剂和/或条件，包括在间苯二酚作为氯清除剂存在的情况下使用二氧化硒、高乐氏漂白剂、活性二氧化锰和亚氯酸钠。
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