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【结 构 式】 
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【分子编号】48864 【品名】(E)-4-(4-bromophenoxy)-2-buten-1-ol 【CA登记号】 |
【 分 子 式 】C10H11BrO2 【 分 子 量 】243.10014 【元素组成】C 49.41% H 4.56% Br 32.87% O 13.16% |
合成路线1
该中间体在本合成路线中的序号：(XV)Alternatively, intermediate (VI) can be obtained as follows: 1,4-Dichloro-2-butene (I) is condensed with p-bromophenol (XII) by means of Cs2CO3 in acetonitrile to give compound (XIII), which is then converted into acetate (XIV) after treatment with ammonium tetrabutyl acetate in refluxing acetone. Saponification of (XIV) with NaOH in MeOH affords alcohol (XV), which is then subjected to Claisen rearrangement by refluxing in ethyl orthoacetate in propionic acid to provide ester (XVI). Reduction of (XVI) with LiAlH4 Et2O gives alcohol (XVII), which is finally condensed with 4-bromophenyltributyl tin (XVIII) by means of Pd(PPh3)4 and LiCl in toluene.
| 【1】 Guilbaud, N.; Atassi, G.; Le Diguarher, T.; Bonnet, J.; Sabatini, M.; Casara, P.; Chollet, A.-M.; Pierre, A.; Tucker, G. (ADIR et Cie.); Carboxylic and hydroxamic acid cpds. inhibiting metalloproteases, method for preparing same and pharmaceutical compsns. containing them. EP 1091937; FR 2780402; WO 0000473 . |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (I) | 32186 | (E)-1,4-dichloro-2-butene | 110-57-6 | C4H6Cl2 | 详情 | 详情 |
| (VI) | 48857 | ethyl 3-[[(4'-bromo[1,1'-biphenyl]-4-yl)oxy]methyl]-4-pentenoate | C20H21BrO3 | 详情 | 详情 | |
| (XII) | 25313 | 4-bromophenol | 106-41-2 | C6H5BrO | 详情 | 详情 |
| (XIII) | 48862 | 1-bromo-4-[[(E)-4-chloro-2-butenyl]oxy]benzene; 4-bromophenyl (E)-4-chloro-2-butenyl ether | C10H10BrClO | 详情 | 详情 | |
| (XIV) | 48863 | (E)-4-(4-bromophenoxy)-2-butenyl acetate | C12H13BrO3 | 详情 | 详情 | |
| (XV) | 48864 | (E)-4-(4-bromophenoxy)-2-buten-1-ol | C10H11BrO2 | 详情 | 详情 | |
| (XVI) | 48865 | ethyl 3-[(4-bromophenoxy)methyl]-4-pentenoate | C14H17BrO3 | 详情 | 详情 | |
| (XVII) | 48866 | 3-[(4-bromophenoxy)methyl]-4-penten-1-ol | C12H15BrO2 | 详情 | 详情 | |
| (XVIII) | 48867 | (4-bromophenyl)(tributyl)stannane | C18H31BrSn | 详情 | 详情 |