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【结 构 式】 
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【分子编号】30575 【品名】methyl 2,5-dioxopentanoate 【CA登记号】 |
【 分 子 式 】C6H8O4 【 分 子 量 】144.12712 【元素组成】C 50% H 5.59% O 44.4% |
合成路线1
该中间体在本合成路线中的序号：(V)The reaction of methyl-2-oxoglutarate (I) with triethyl orthoformate (A) by means of H2SO4 in refluxing methanol gives methyl 2,2-diethoxyglutarate (II), which is hydrolyzed partially with NaOH in water yielding methyl 2,2-diethoxy-4-carboxybutanoate (III). The reduction of (III) with NaBH4 and BF3 ethearate affords methyl 5-hydroxy-2-oxopentanoate (IV). The controlled oxidation of (IV) with pyridinium chlorochromate and sodium acetate in methylene chloride gives methyl 2,5-dioxopentanoate (V), which is condensed with N-ethyltryptamine (VI) by means of acetic acid in refluxing benzene yielding the tricyclic ketoester (VII). Finally, this compound cyclizes again spontaneously.
| 【1】 Hannart, J.A.A.J. (OmniChem); Indole derivatives and therapeutically acting drugs. BE 0870887; DE 2842418; FR 2404639; GB 2005267; JP 7988300; JP 8331352; US 4200638 . |
| 【2】 Castaner, J.; Serradell, M.N.; Vinconate. Drugs Fut 1984, 9, 4, 283. |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (A) | 21304 | Triethyl orthoformate; 1-(Diethoxymethoxy)ethane; Diethoxymethyl ethyl ether | 122-51-0 | C7H16O3 | 详情 | 详情 |
| (I) | 30571 | dimethyl 2-oxopentanedioate | 13192-04-6 | C7H10O5 | 详情 | 详情 |
| (II) | 30572 | dimethyl 2,2-diethoxypentanedioate | C11H20O6 | 详情 | 详情 | |
| (III) | 30573 | 4,4-diethoxy-5-methoxy-5-oxopentanoic acid | C10H18O6 | 详情 | 详情 | |
| (IV) | 30574 | 5-methoxy-4,5-dioxopentanoic acid | C6H8O5 | 详情 | 详情 | |
| (V) | 30575 | methyl 2,5-dioxopentanoate | C6H8O4 | 详情 | 详情 | |
| (VI) | 30576 | N-ethyl-2-(1H-indol-3-yl)-1-ethanamine; N-ethyl-N-[2-(1H-indol-3-yl)ethyl]amine | C12H16N2 | 详情 | 详情 | |
| (VII) | 30577 | methyl 4-(2-ethyl-2,3,4,9-tetrahydro-1H-beta-carbolin-1-yl)-2-oxobutanoate | C18H22N2O3 | 详情 | 详情 |