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【结 构 式】 
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【分子编号】58875 【品名】4-formylbenzenesulfonamide 【CA登记号】 |
【 分 子 式 】C7H7NO3S 【 分 子 量 】185.20352 【元素组成】C 45.4% H 3.81% N 7.56% O 25.92% S 17.31% |
合成路线1
该中间体在本合成路线中的序号：(III)Diazotization of sulfanilamide (I), followed by treatment of the resultant diazonium salt with potassium cyanide/copper sulfate under Sandmeyer conditions, leads to nitrile (II). Stephen reduction of (II) with Raney nickel alloy in 75% aqueous formic acid gives the benzaldehyde (III), which is further reduced to the benzyl alcohol (IV) using NaBH4 in ethanol. Treatment of alcohol (IV) with PBr3 provides the benzyl bromide (V). This is then subjected to Arbuzov reaction with triethyl phosphite to produce phosphonate (VI). Finally, Wittig-Horner condensation of (VI) with 4-fluorobenzaldehyde (VII) furnishes the target stilbene derivative.
| 【1】 Lin, S.-J.; Hsu, F.-L.; Yang, T.-H.; Yang, L.-M.; Antitumor agents. Part 3: Synthesis and cytotoxicity of new trans-stilbene benzenesulfonomide derivatives. Bioorg Med Chem Lett 2002, 12, 7, 1013. |
| 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) | 54719 | 4-Aminobenzenesulfonamide; p-Aminobenzene sulfonyl amide; p-Aminobenzenesulfonamide; p-Anilinesulfonamide; Sulfanilamide | 63-74-1 | C6H8N2O2S | 详情 | 详情 |
| (II) | 58874 | 4-Cyanobenzenesulphonamide | C7H6N2O2S | 详情 | 详情 | |
| (III) | 58875 | 4-formylbenzenesulfonamide | C7H7NO3S | 详情 | 详情 | |
| (IV) | 58876 | 4-(hydroxymethyl)benzenesulfonamide | C7H9NO3S | 详情 | 详情 | |
| (V) | 58877 | 4-(bromomethyl)benzenesulfonamide | C7H8BrNO2S | 详情 | 详情 | |
| (VI) | 58878 | diethyl 4-(aminosulfonyl)benzylphosphonate | C11H18NO5PS | 详情 | 详情 | |
| (VII) | 12337 | 4-fluorobenzaldehyde | 459-57-4 | C7H5FO | 详情 | 详情 |