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【结 构 式】

【分子编号】29147

【品名】8-acetyl-7-hydroxy-4,6-dimethyl-2H-chromen-2-one

【CA登记号】

【 分 子 式 】C13H12O4

【 分 子 量 】232.23588

【元素组成】C 67.23% H 5.21% O 27.56%

与该中间体有关的原料药合成路线共 1 条

合成路线1

该中间体在本合成路线中的序号:(II)

4,6-Dimethyl-7-acetylumbelliforone (4,6-dimethyl-7-acetoxycoumarin) (I) is submitted to the Fries' rearrangement, obtaining the 4,6-dimethyl-8-acetylumbelliferone (II); the latter (II) is condensed with ethylbromoacetate (A) and the resulting ethyl [(4,6-dimethyl-8-acetyl-7-coumarinyl)oxy]acetate (III) is hydrolyzed by refluxing with 5% KOH aqueous methanolic solution; from this solution, acidified with HCl, the [(4,6-dimethyl-8-acetyl-7-coumarinyl)oxy]acetic acid (IV) is extracted with EtOAc and purified by crystallization (EtOAc / n-hexane). Cyclization of (IV), carried out by refluxing in Ac2O in the presence of anhydrous natrium acetate, is accompanied by an almost complete decarboxylation of (V), yielding 4,6,4'-trimethylangelicin (TMA).

1 Guiotto, A.; et al.; 6-Methylangelicins: A new series of potential photochemotherapheutic agents for the treatment of psoriasis. J Med Chem 1984, 27, 8, 959.
2 Bordin, F.; Dall'Acqua, F.; Cristofolini, M.; Guiotto, A.; 4,6,4'-Trimethylangelicin. Drugs Fut 1985, 10, 4, 307.
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(A) 16640 Ethyl 2-bromoacetate; Ethyl bromoacetate 105-36-2 C4H7BrO2 详情 详情
(I) 29146 4,6-dimethyl-2-oxo-2H-chromen-7-yl acetate C13H12O4 详情 详情
(II) 29147 8-acetyl-7-hydroxy-4,6-dimethyl-2H-chromen-2-one C13H12O4 详情 详情
(III) 29148 ethyl 2-[(8-acetyl-4,6-dimethyl-2-oxo-2H-chromen-7-yl)oxy]acetate C17H18O6 详情 详情
(IV) 29149 2-[(8-acetyl-4,6-dimethyl-2-oxo-2H-chromen-7-yl)oxy]acetic acid C15H14O6 详情 详情
(V) 29150 4,6,9-trimethyl-2-oxo-2H-furo[2,3-h]chromene-8-carboxylic acid C15H12O5 详情 详情
Extended Information