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【结 构 式】 
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【分子编号】40471 【品名】ethyl 7-hydroxy-9-oxo-9H-xanthene-2-carboxylate 【CA登记号】 |
【 分 子 式 】C16H12O5 【 分 子 量 】284.26828 【元素组成】C 67.6% H 4.25% O 28.14% |
合成路线1
该中间体在本合成路线中的序号：(III)By cleavage of the 7-methoxy-9-oxoxanthene-2-carboxylic acid (I) with AlCl3 in xylene to give 7-hydroxy-9-oxoxanthene-2-carboxylic acid (II), which is then esterified with ethanol and anhydrous HCl to the corresponding ethyl ester (III). This product is treated first with ethylene oxide (A) in DMF, and finally hydrolyzed with NaOH in ethanol-water. The condensation of 2-chloro-5-nitrobenzoic acid (IV) with 4-methoxyphenol (V) by means of K2CO3, Cu and Cu2I2 in n-pentanol gives 2-(4-methoxyphenoxy)-5-nitrobenzoic acid (VI), which is cyclized with concentrated H2SO4 to 7-methoxy-2-nitroxanthone (VII). The reduction of the nitro group of (VII) with SnCl2 in concentrated HCl yields 7-methoxy-2-aminoxanthone (VIII). Finally, this product is treated first with NaNO2 - HCl, then with NaCN and finally hydrolyzed with H2SO4 to afford 7-methoxy-9-oxoxanthene-2-carboxylic acid.
| 【1】 Castaner, J.; Blancafort, P.; AH 7725. Drugs Fut 1976, 1, 7, 313. |
| 【2】 Bays, D.E.; Xanthone derivatives.. DE 2058295; FR 2073425; GB 1312620; US 3706768 . |
| 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) | 10393 | Oxirane; Ethylene oxide | 75-21-8 | C2H4O | 详情 | 详情 |
| (I) | 40469 | 7-methoxy-9-oxo-9H-xanthene-2-carboxylic acid | C15H10O5 | 详情 | 详情 | |
| (II) | 40470 | 7-hydroxy-9-oxo-9H-xanthene-2-carboxylic acid | C14H8O5 | 详情 | 详情 | |
| (III) | 40471 | ethyl 7-hydroxy-9-oxo-9H-xanthene-2-carboxylate | C16H12O5 | 详情 | 详情 | |
| (IV) | 10198 | 4-Chlorophenyl thiocyanate | 3226-37-7 | C7H4ClNS | 详情 | 详情 |
| (V) | 32744 | 4-methoxyphenol | 150-76-5 | C7H8O2 | 详情 | 详情 |
| (VI) | 40466 | 2-(4-methoxyphenoxy)-5-nitrobenzoic acid | C14H11NO6 | 详情 | 详情 | |
| (VII) | 40467 | 2-methoxy-7-nitro-9H-xanthen-9-one | C14H9NO5 | 详情 | 详情 | |
| (VIII) | 40468 | 2-amino-7-methoxy-9H-xanthen-9-one | C14H11NO3 | 详情 | 详情 |