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【结 构 式】 
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【分子编号】64272 【品名】2-methoxy-5-nitrophenol 【CA登记号】 |
【 分 子 式 】C7H7NO4 【 分 子 量 】169.13692 【元素组成】C 49.71% H 4.17% N 8.28% O 37.84% |
合成路线1
该中间体在本合成路线中的序号：(I)Alkylation of 2-methoxy-5-nitrophenol (I) with cyclopentyl bromide (II) provides the cyclopentyl ether (III). Subsequent reduction of the nitro derivative (III) to aniline (IV) is effected by transfer hydrogenation in the presence of ammonium formate and Pd/C. Condensation of 3-(cyclopentyloxy)-4-methoxyaniline (IV) with 4-nitrophthalic anhydride (V) gives rise to phthalimide (VI). Reduction of imide (VI) by means of NaBH4 furnishes the amide alcohol (VII), which is further cyclized to isoindoline (VIII) under Mitsunobu conditions. Finally, transfer hydrogenation of nitro isoindoline (VIII) gives rise to the corresponding amine.
| 【1】 Park, J.S.; Moon, S.C.; Baik, K.U.; Cho, J.Y.; Yoo, E.S.; Byun, Y.S.; Park, M.H.; Synthesis and SAR studies for the inhibition of TNF-alpha production. Part 2. 2-[3-(Cyclopentyloxy)-4-methoxyphenyl]-substituted-1-isoindolinone derivatives. Arch Pharmacal Res 2002, 25, 2, 137. |
| 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) | 64272 | 2-methoxy-5-nitrophenol | C7H7NO4 | 详情 | 详情 | |
| (II) | 10972 | 1-Bromocyclopentane; Cyclopentyl bromide | 137-43-9 | C5H9Br | 详情 | 详情 |
| (III) | 64273 | cyclopentyl 2-methoxy-5-nitrophenyl ether; 2-(cyclopentyloxy)-1-methoxy-4-nitrobenzene | C12H15NO4 | 详情 | 详情 | |
| (IV) | 64274 | 3-(cyclopentyloxy)-4-methoxyphenylamine; 3-(cyclopentyloxy)-4-methoxyaniline | C12H17NO2 | 详情 | 详情 | |
| (V) | 31028 | 5-nitro-2-benzofuran-1,3-dione | 5466-84-2 | C8H3NO5 | 详情 | 详情 |
| (VI) | 64275 | 2-[3-(cyclopentyloxy)-4-methoxyphenyl]-5-nitro-1H-isoindole-1,3(2H)-dione | C20H18N2O6 | 详情 | 详情 | |
| (VII) | 64276 | N-[3-(cyclopentyloxy)-4-methoxyphenyl]-2-(hydroxymethyl)-5-nitrobenzamide | C20H22N2O6 | 详情 | 详情 | |
| (VIII) | 64277 | 2-[3-(cyclopentyloxy)-4-methoxyphenyl]-6-nitro-1-isoindolinone | C20H20N2O5 | 详情 | 详情 |