【结 构 式】 |
【分子编号】13141 【品名】methyl 7-[3-(4-acetyl-3-methoxy-2-propylphenoxy)propoxy]-8-propyl-2-chromanecarboxylate 【CA登记号】 |
【 分 子 式 】C29H38O7 【 分 子 量 】498.61652 【元素组成】C 69.86% H 7.68% O 22.46% |
合成路线1
该中间体在本合成路线中的序号:(V)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 |