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【结 构 式】 
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【分子编号】43808 【品名】2-bromo-1-(4-octylphenyl)-1-ethanone 【CA登记号】 |
【 分 子 式 】C16H23BrO 【 分 子 量 】311.26202 【元素组成】C 61.74% H 7.45% Br 25.67% O 5.14% |
合成路线1
该中间体在本合成路线中的序号：(III)A new synthesis of FTY-720 has been described: The Friedel Crafts condensation of octylbenzene (I) with bromoacetyl chloride (II) by means of AlCl3 in dichloromethane gives the phenacyl bromide (III), which is condensed with 2-acetamidomalonic acid diethyl ester (IV) by means of EtONa in ethanol/THF to yielding the ketone-malonic ester adduct (V). Reduction of (V) with Et3SiH by means of TiCl4 in dichloromethane affords compound (VI), which is then reduced with LiAlH4 in THF followed by acetylation with acetic anhydride and pyridine to provide the acetate (VII). Finally, compound (VII) is hydrolyzed with LiOH in refluxing methanol/water and treated with HCl in ethyl ether.
| 【1】 Renault, P.; Durand, P.; Peralba, P.; Sierra, F.; A new efficient synthesis of the immunosuppressive agent FTY-720. Synthesis 2000, 4, 505. |
| 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) | 43807 | 1-octylbenzene | 2189-60-8 | C14H22 | 详情 | 详情 |
| (II) | 27903 | 2-Bromoacetyl chloride | 22118-09-8 | C2H2BrClO | 详情 | 详情 |
| (III) | 43808 | 2-bromo-1-(4-octylphenyl)-1-ethanone | C16H23BrO | 详情 | 详情 | |
| (IV) | 16710 | Diethyl 2-(acetamido)malonate; Diethyl acetamidomalonate | 1068-90-2 | C9H15NO5 | 详情 | 详情 |
| (V) | 43809 | diethyl 2-(acetamido)-2-[2-(4-octylphenyl)-2-oxoethyl]malonate | C25H37NO6 | 详情 | 详情 | |
| (VI) | 16711 | diethyl 2-(acetamido)-2-(4-octylphenethyl)malonate | C25H39NO5 | 详情 | 详情 | |
| (VII) | 16712 | 2-(acetamido)-2-[(acetoxy)methyl]-4-(4-octylphenyl)butyl acetate | C25H39NO5 | 详情 | 详情 |