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【结 构 式】

【分子编号】13138

【品名】1-[4-(3-Bromopropoxy)-2-hydroxy-3-propylphenyl]-1-ethanone

【CA登记号】

【 分 子 式 】C14H19BrO3

【 分 子 量 】315.20706

【元素组成】C 53.35% H 6.08% Br 25.35% O 15.23%

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)

The reaction of 2,4-dihydroxy-3-n-propylacetophenone (I) with excess 1,3-dibromopropane in the presence of potassium carbonate in dimethylformamide gives 3-(2-n-propyl-3-hydroxy-4-acetylphenoxy)-1-bromopropane (II). Subsequent reaction of (II) with 2-carbomethoxy-7-hydroxy-8-n-propylchromone in dimethylformamide containing anhydrous potassium carbonate furnished 2-carbomethoxy-7-[5-(2-n-propyl-3-hydroxy-4-acetylphenoxy)propoxy]-8-n-propylchromone (III), m.p. 113-115 C. Hydrogenation of (III) in acetic acid with 5% palladium on carbon catalyst generated 2-carbomethoxy-7-[5-(2-n-propyl-3-hydroxy-4-acetylphenoxy)propoxy]-8-n-propylchroman (IV), m.p. 70-72 C. Subsequent alkylation of (IV) with excess methyl iodide in refluxing acetone containing anhydrous potassium carbonate produced O-methyl ester (V). Final hydrolysis of O-methyl ester (V) was carried out with lithium hydroxide in aqueous methanol to provide SC-41930.

1 Djuric, S.W.; Collins, P.W.; Jones, P.H.; et al.; 7-[3-(4-Acetyl-3-methoxy-2-propylphenoxy)propoxy]-3,4-dihydro-8-propyl- 2H-1-benzopyran-2-carboxylic acid: An orally active selective leukotriene B4 receptor antagonist. J Med Chem 1989, 32, 6, 1145-7.
2 Shone, R.L.; Djuric, S.W.; Tsai, B.S.; Fretland, D.J.; Gaginella, T.S.; Cook, C.S.; SC-41930. Drugs Fut 1990, 15, 7, 695.
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
63538 methyl 7-hydroxy-4-oxo-8-propyl-2-chromanecarboxylate C14H16O5 详情 详情
(I) 13137 2',4'-Dihydroxy-3'-propylacetophenone; 1-(2,4-Dihydroxy-3-propylphenyl)-1-ethanone 40786-69-4 C11H14O3 详情 详情
(II) 13138 1-[4-(3-Bromopropoxy)-2-hydroxy-3-propylphenyl]-1-ethanone C14H19BrO3 详情 详情
(III) 13139 methyl 7-[3-(4-acetyl-3-hydroxy-2-propylphenoxy)propoxy]-4-oxo-8-propyl-2-chromanecarboxylate C28H34O8 详情 详情
(IV) 13140 methyl 7-[3-(4-acetyl-3-hydroxy-2-propylphenoxy)propoxy]-8-propyl-2-chromanecarboxylate C28H36O7 详情 详情
(V) 13141 methyl 7-[3-(4-acetyl-3-methoxy-2-propylphenoxy)propoxy]-8-propyl-2-chromanecarboxylate C29H38O7 详情 详情
Extended Information