【结 构 式】 |
【分子编号】64424 【品名】4-[4-(2-bromoethoxy)phenyl]-1-butanol 【CA登记号】 |
【 分 子 式 】C12H17BrO2 【 分 子 量 】273.16978 【元素组成】C 52.76% H 6.27% Br 29.25% O 11.71% |
合成路线1
该中间体在本合成路线中的序号:(VI)4-Iodophenol (I) is alkylated with 1,2-dibromoethane (II) to afford 1-(2-bromoethoxy)-4-iodobenzene (III). Subsequent palladium-catalyzed coupling of aryl iodide (III) with 3-butyn-1-ol (IV) furnishes the phenylbutynol adduct (V), which is further hydrogenated in the presence of Pd/C to the saturated alcohol (VI). Condensation of the alkyl bromide (VI) with (R)-p-chlorobenzhydrylpiperazine (VII) produces the dialkylated piperazine (VIII). Then, Mitsunobu coupling of arylbutanol (VIII) with phenoxycarbonylaminophenoxyformate (IX) leads to the protected hydroxamic acid (X). This is finally treated with methanolic ammonia to provide the title N-hydroxyurea derivative.
【1】 Chatelain, P.; Differding, E.; Cai, X.; Hussoin, S.; Grewal, G.; Young, M.; Lewis, T.; Toy-Palmer, A.; Scannel, R.; Ellis, J.; Lassoie, M.-A. (UCB SA); Cpds. and methods for treatment of asthma, allergy and inflammatory disorders. JP 2002540198; US 6451801; WO 0058295 . |
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) | 22242 | 4-iodophenol | 540-38-5 | C6H5IO | 详情 | 详情 |
(II) | 10252 | 1,2-Dibromoethane; Ethylene dibromide | 106-93-4 | C2H4Br2 | 详情 | 详情 |
(III) | 64422 | 1-(2-bromoethoxy)-4-iodobenzene; 2-bromoethyl 4-iodophenyl ether | C8H8BrIO | 详情 | 详情 | |
(IV) | 32507 | 3-butyn-1-ol | 927-74-2 | C4H6O | 详情 | 详情 |
(V) | 64423 | 4-[4-(2-bromoethoxy)phenyl]-3-butyn-1-ol | C12H13BrO2 | 详情 | 详情 | |
(VI) | 64424 | 4-[4-(2-bromoethoxy)phenyl]-1-butanol | C12H17BrO2 | 详情 | 详情 | |
(VII) | 30404 | 1-[(R)-(4-chlorophenyl)(phenyl)methyl]piperazine | C17H19ClN2 | 详情 | 详情 | |
(VIII) | 64425 | 4-[4-(2-{4-[(R)-(4-chlorophenyl)(phenyl)methyl]-1-piperazinyl}ethoxy)phenyl]-1-butanol | C29H35ClN2O2 | 详情 | 详情 | |
(IX) | 19646 | 1-[([[(phenoxycarbonyl)oxy]amino]carbonyl)oxy]benzene | C14H11NO5 | 详情 | 详情 | |
(X) | 64426 | 1-[(R)-(4-chlorophenyl)(phenyl)methyl]-4-{2-[4-(4-{(phenoxycarbonyl)[(phenoxycarbonyl)oxy]amino}butyl)phenoxy]ethyl}piperazine | C43H44ClN3O6 | 详情 | 详情 |