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【结 构 式】 
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【分子编号】20620 【品名】4-methoxy-3-(tetrahydro-3-furanyloxy)benzaldehyde 【CA登记号】 |
【 分 子 式 】C12H14O4 【 分 子 量 】222.24076 【元素组成】C 64.85% H 6.35% O 28.8% |
与该中间体有关的原料药合成路线共 1 条
合成路线1
该中间体在本合成路线中的序号：(III)Coupling of isovanillin (I) with 3-hydroxytetrahyrofuran (II) in the presence of triphenyl phosphine and diisopropyl azodicarboxylate yielded the tetrahydrofuryl ether (III). Subsequent oxidation of the aldehyde using sodium chlorite and sulfamic acid gave carboxylic acid (IV), which was further converted to acid chloride (V) upon treatment with SOCl2 in toluene. Finally, condensation of (V) with 4-amino-3,5-dimethylisoxazole (VI) provided the title compound.
| 【1】 Tober, C.; Rundfeldt, C.; Rostock, A.; Bartsch, R.; Nickel, B.; Szeleny, I.; Herbst, M.; Dieter, R.; Olbrich, A.; Kutscher, B.; Sauer, W.; Jainta, H.; Jahn, W.; Engel, J.; D-23129. Drugs Fut 1995, 20, 11, 1112. |
| 【2】 Fenton, G.; Palfreyman, M.N.; Thurairatnam, S. (Aventis Pharma SA); Substd. aromatic cpds. as cAMP phosphodiesterase- and TNF-inhibitors. EP 0741707; JP 1997509654; WO 9520578 . |
| 【3】 Dieter, H.-R.; Engel, J.; Kutscher, B.; Polymeropoulos, E.; Szelenyi, S.; Nickel, B. (Asta Medica AG); Novel 1,2,4-Triaminobenzene derivs. and process for their preparation. DE 4200259; EP 0554543; JP 1993345752; US 5384330 . |
| 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) | 18455 | 3-hydroxy-4-methoxybenzaldehyde; Isovanillin | 621-59-0 | C8H8O3 | 详情 | 详情 |
| (II) | 20619 | tetrahydro-3-furanol | 453-20-3 | C4H8O2 | 详情 | 详情 |
| (III) | 20620 | 4-methoxy-3-(tetrahydro-3-furanyloxy)benzaldehyde | C12H14O4 | 详情 | 详情 | |
| (IV) | 20621 | 4-methoxy-3-(tetrahydro-3-furanyloxy)benzoic acid | C12H14O5 | 详情 | 详情 | |
| (V) | 20622 | 4-methoxy-3-(tetrahydro-3-furanyloxy)benzoyl chloride | C12H13ClO4 | 详情 | 详情 | |
| (VI) | 20623 | 3,5-dimethyl-4-isoxazolamine; 3,5-dimethyl-4-isoxazolylamine | C5H8N2O | 详情 | 详情 |
Extended Information