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【结 构 式】 
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【分子编号】17789 【品名】2-Fluoro-4-hydroxybenzonitrile 【CA登记号】82380-18-5 |
【 分 子 式 】C7H4FNO 【 分 子 量 】137.1133032 【元素组成】C 61.32% H 2.94% F 13.86% N 10.22% O 11.67% |
合成路线1
该中间体在本合成路线中的序号：(IV)Treatment of 4-hydroxy-3-methoxybenzoic acid (I) with thionyl chloride and then with diisopropyl amine provided amide (II). Alkylation of (II) with 1,4-dibromobutane and potassium carbonate in acetonitrile, followed by treatment with sodium iodide afforded iodobutylether (III). Then, alkylation of 2-fluoro-4-hydroxybenzonitrile (IV) with iodide (III) in the presence of sodium hydride in DMF gave (V), which was condensed with acetone oxime (VI) and potassium tert-butoxide to provide (VII). Finally, cyclization of (VII) in a refluxing hydroalcoholic solution of HCl generated the target benzisoxazole.
| 【1】 Suh, H.; et al.; 3-Amino-1,2-benzisoxazoles: A new family of potent inhibitors of LTB4 binding to the human neutrophils. Bioorg Med Chem Lett 1997, 7, 4, 389. |
| 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) | 17786 | 4-hydroxy-3-methoxybenzoic acid; Vanillic acid | 121-34-6 | C8H8O4 | 详情 | 详情 |
| (II) | 17787 | 4-hydroxy-N,N-diisopropyl-3-methoxybenzamide | C14H21NO3 | 详情 | 详情 | |
| (III) | 17788 | 4-(4-iodobutoxy)-N,N-diisopropyl-3-methoxybenzamide | C18H28INO3 | 详情 | 详情 | |
| (IV) | 17789 | 2-Fluoro-4-hydroxybenzonitrile | 82380-18-5 | C7H4FNO | 详情 | 详情 |
| (V) | 17790 | 4-[4-(4-cyano-3-fluorophenoxy)butoxy]-N,N-diisopropyl-3-methoxybenzamide | C25H31FN2O4 | 详情 | 详情 | |
| (VI) | 17791 | acetone oxime; Acetoxime | 127-06-0 | C3H7NO | 详情 | 详情 |
| (VII) | 17792 | 4-[4-(4-cyano-3-[[(1-methylethylidene)amino]oxy]phenoxy)butoxy]-N,N-diisopropyl-3-methoxybenzamide | C28H37N3O5 | 详情 | 详情 |