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【结 构 式】 
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【分子编号】34619 【品名】1-(3-thienyl)-1-ethanone 【CA登记号】1468-83-3 |
【 分 子 式 】C6H6OS 【 分 子 量 】126.17904 【元素组成】C 57.11% H 4.79% O 12.68% S 25.41% |
合成路线1
该中间体在本合成路线中的序号：(I)Oxidation of 3-acetylthiophene (I) with selenium dioxide in refluxing dioxan provided 3-thienylglyoxaldehyde hydrate (II). This was then condensed with 4,5-dimethoxy-1,2-phenylenediamine (III) in boiling EtOH to produce the target quinoxaline, which was finally isolated as the hydrochloride salt.
| 【1】 Myers, M.R.; Maguirre, M.P.; Spada, A.P.; Persons, P.E. (Aventis Pharmaceuticals, Inc.); Bis mono- and bicyclic aryl and heteroaryl cpds. which inhibit EGF and/or PDGF receptor tyrosine kinase. US 5480883 . |
合成路线2
该中间体在本合成路线中的序号：(II)Mannich reaction of N-(2-methoxyphenyl)piperazine (I) with 3-acetylthiophene (II) in the presence of paraformaldehyde and HCl in refluxing EtOH leads to the piperazinyl propanone (III). Subsequent keto group reduction with NaBH4 gives alcohol (IV). This is then condensed with 1-fluoronaphthalene (V) in the presence of NaH to produce the title naphthyl ether.
| 【1】 Oficialdegui, A.-M.; Martínez-Esparza, J.; Pérez-Sailanes, S.; et al.; New 1-aryl-3-(4-arylpiperazin-1-yl)propane derivatives, with dual action at 5-HT1A serotonin receptors and serotonin transporter, as a new class of antidepressants. J Med Chem 2001, 44, 3, 418. |
| 【2】 Bosch Rovira, A.; Roca Acin, J.; Monge Vega, A.; Del Rio Zambrana, J.; Palop Cubillo, J.A.; Lasheras Aldaz, B.; Del Castillo Nieto, J.C. (Laboratorios Vita, SA); Cpds. derived from thiophene and benzothiophene, and related utilisation and compsn.. EP 1008594; ES 2128266; JP 2002511883; US 6262056; WO 9902516 . |
| 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) | 11882 | 1-(2-Methoxyphenyl)piperazine; Methyl 2-piperazinophenyl ether; 1-(2-Methoxyphenyl)-piperazine | 35386-24-4 | C11H16N2O | 详情 | 详情 |
| (II) | 34619 | 1-(3-thienyl)-1-ethanone | 1468-83-3 | C6H6OS | 详情 | 详情 |
| (III) | 57497 | 3-[4-(2-methoxyphenyl)-1-piperazinyl]-1-(3-thienyl)-1-propanone | C18H22N2O2S | 详情 | 详情 | |
| (IV) | 57498 | 3-[4-(2-methoxyphenyl)-1-piperazinyl]-1-(3-thienyl)-1-propanol | C18H24N2O2S | 详情 | 详情 | |
| (V) | 40503 | 1-fluoronaphthalene | 321-38-0 | C10H7F | 详情 | 详情 |