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【结 构 式】 
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【分子编号】17793 【品名】m-cresol; m-Methylphenol 【CA登记号】108-39-4 |
【 分 子 式 】C7H8O 【 分 子 量 】108.13992 【元素组成】C 77.75% H 7.46% O 14.8% |
合成路线1
该中间体在本合成路线中的序号：(I)The condensation of 3-methylphenol (I) and epichlorohydrin (II) by means of NaOH gives 1,2-epoxy-3-(3-methylphenoxy)propane (III), which is then condensed with 3,4-dimethoxyphenylethylamine (V) by heating their mixture at 95-100 C.
| 【1】 Holmes, A.; Meyer, R.F.; New aminoalkanol compounds and methods for their production. FR 2163486; GB 1344976; JP 48067232 . |
| 【2】 Milton, L.H.; et al.; Cardioselective beta-adrenergic blocking agents. 1. 1-[3,4-(dimethoxyphenethyl)amino]-3-aryloxy-2-propanols. J Med Chem 1975, 18, 2, 148-152. |
| 【3】 Castaner, J.; Weetman, D.F.; Bevantol. Drugs Fut 1977, 2, 8, 500. |
| 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) | 17793 | m-cresol; m-Methylphenol | 108-39-4 | C7H8O | 详情 | 详情 |
| (II) | 10146 | Epichlorohydrin; 2-(Chloromethyl)oxirane | 106-89-8 | C3H5ClO | 详情 | 详情 |
| (III) | 33968 | 2-[(3-methylphenoxy)methyl]oxirane; 3-methylphenyl 2-oxiranylmethyl ether | C10H12O2 | 详情 | 详情 | |
| (V) | 10098 | 2-(3,4-Dimethoxyphenyl)-1-ethanamine; 3,4-Dimethoxyphenethylamine; 2-(3,4-Dimethoxyphenyl)ethylamine | 120-20-7 | C10H15NO2 | 详情 | 详情 |
合成路线2
该中间体在本合成路线中的序号：(I)The condensation of 3-methylphenol (I) with epichlorohydrin (II) by means of a catalytic amount of piperidine gives 1-(3-methylphenoxy)-3-chloro-2-propanol (IV), which is then condensed with 3,4-dimethoxyphenylethylamine (V) by heating their mixture at 95-100 C.
| 【1】 Holmes, A.; Meyer, R.F.; New aminoalkanol compounds and methods for their production. FR 2163486; GB 1344976; JP 48067232 . |
| 【2】 Milton, L.H.; et al.; Cardioselective beta-adrenergic blocking agents. 1. 1-[3,4-(dimethoxyphenethyl)amino]-3-aryloxy-2-propanols. J Med Chem 1975, 18, 2, 148-152. |
| 【3】 Castaner, J.; Weetman, D.F.; Bevantol. Drugs Fut 1977, 2, 8, 500. |
| 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) | 17793 | m-cresol; m-Methylphenol | 108-39-4 | C7H8O | 详情 | 详情 |
| (II) | 10146 | Epichlorohydrin; 2-(Chloromethyl)oxirane | 106-89-8 | C3H5ClO | 详情 | 详情 |
| (IV) | 33967 | 1-chloro-3-(3-methylphenoxy)-2-propanol | C10H13ClO2 | 详情 | 详情 | |
| (V) | 10098 | 2-(3,4-Dimethoxyphenyl)-1-ethanamine; 3,4-Dimethoxyphenethylamine; 2-(3,4-Dimethoxyphenyl)ethylamine | 120-20-7 | C10H15NO2 | 详情 | 详情 |
合成路线3
该中间体在本合成路线中的序号：(I)The compound is prepared by condensation of 3-methylphenol (I) with ethyl 1-benzyl-4-oxo-3-piperidine carboxylate hydrochloride (II) in aqueous sulfuric acid at room temperature.
| 【1】 Unangst, P.C.; et al.; Chromeno[3,4-c]pyridin-5-ones: Selective human dopamine D4 receptor antagonists as potential antipsychotic agents. J Med Chem 1997, 40, 17, 2688. |
合成路线4
该中间体在本合成路线中的序号：(I)Cyclization of m-cresol (I) with ethyl 2-oxocyclohexanecarboxylate (II) in H2SO4 afforded tricyclic benzopyranone (III). This was treated with MeMgBr in boiling anisole to provide the tricyclic dimethylbenzopyran (IV). Dehydrogenation of (IV) using 2,3-dichloro-5,6-dicyano-1,4-benzoquinone gave dibenzopyran (V), which by further bromination with N-bromosuccinimide and 2,2'-azobis(4-methoxy-2,4-dimethylvaleronitrile) produced bromide (VI). Finally, N-alkylation of 4-(3-indolyl)butyric acid (VII) with bromide (VI) in the presence of two equivalents of NaH yielded the title compound.
| 【1】 Sawada, K.; Hirai, H.; Golden, P.; Okada, S.; Sawada, Y.; Hashimoto, M.; Tanaka, H.; (1-Benzylindole-3-yl)-alkanoic acids; novel nonsteroidal inhibitors of steroid 5alpha-reductase (I). Chem Pharm Bull 1998, 46, 11, 1683. |
| 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) | 17793 | m-cresol; m-Methylphenol | 108-39-4 | C7H8O | 详情 | 详情 |
| (II) | 11889 | ethyl 2-oxocyclohexanecarboxylate; Ethyl 2-cyclohexanonecarboxylate | 1655-07-8 | C9H14O3 | 详情 | 详情 |
| (III) | 26528 | 3-methyl-7,8,9,10-tetrahydro-6H-benzo[c]chromen-6-one | C14H14O2 | 详情 | 详情 | |
| (IV) | 26529 | 3,6,6-trimethyl-7,8,9,10-tetrahydro-6H-benzo[c]chromene | C16H20O | 详情 | 详情 | |
| (V) | 26530 | 3,6,6-trimethyl-6H-benzo[c]chromene | C16H16O | 详情 | 详情 | |
| (VI) | 26531 | 3-(bromomethyl)-6,6-dimethyl-6H-benzo[c]chromene | C16H15BrO | 详情 | 详情 | |
| (VII) | 26532 | Indole-3-butyric acid; 4-(3-Indolyl)butyric acid; 4-(1H-Indol-3-yl)butyric acid | 133-32-4 | C12H13NO2 | 详情 | 详情 |