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【结 构 式】 
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【分子编号】60966 【品名】2-(2-isopropyl-2,3-dihydro-1H-inden-5-yl)-1-(4-morpholinyl)-1-ethanethione 【CA登记号】 |
【 分 子 式 】C18H25NOS 【 分 子 量 】303.46864 【元素组成】C 71.24% H 8.3% N 4.62% O 5.27% S 10.57% |
合成路线1
该中间体在本合成路线中的序号：(XI)The Friedel-Kraft's reaction of 2-isopropylindan (I) with acetic anhydride in methylene chloride gives 2-isopropyl-5-acetylindan (VII), which by with sulfur and morpholine (A) at 140 C gives 2-(2-isopropyl-5-indanyl)acetylmorpholinothioamide (XI), which is hydrolyzed to 2-(2-isopropyl-5-indanyl)acetic acid (XII). The esterification of (XII) with ethanol - H2SO4 yields the corresponding ethyl ester (XIII), which is condensed with diethyl carbonate (XIV) by means of sodium ethoxide in refluxing ethanol affording diethyl (2-isopropyl-5-indanyl)malonate (XV), which is methylated with methyl iodide and sodium ethoxide in refluxing ethanol to give diethyl methyl-(2-isopropyl-5-indanyl)malonate (XVI). Finally this compound is hydrolyzed and decarboxylated by treatment with NaOH in refluxing hydrazine hydrate Compound (XII) can also be obtained by a Wolf-Kistner reduction of ketoacid (IV) in refluxing hydrazine hydrate
| 【1】 Teulon, J,M,; et al. (Hexachimie SA); BE 824522; CA 1063618; CH 603533; CH 605567; DD 117209; DD 118271; DD 123319; DE 2504689; FR 2260334; GB 1492175; JP 76125367; JP 76125368; NL 7501518; NL 7501519; US 4069326; US 4088787; US 4182896; ZA 7500707 . |
| 【2】 Blancafort, P.; Serradell, M.N.; Castaner, J.; Arrigoni, Martelli, E.; Isoprofen. Drugs Fut 1981, 6, 8, 471. |
| 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) | 10388 | Morpholine | 110-91-8 | C4H9NO | 详情 | 详情 |
| (I) | 60960 | 2-isopropylindane | C12H16 | 详情 | 详情 | |
| (IV) | 60962 | 2-(2-isopropyl-2,3-dihydro-1H-inden-5-yl)-2-oxoacetic acid | C14H16O3 | 详情 | 详情 | |
| (VII) | 60965 | 1-(2-isopropyl-2,3-dihydro-1H-inden-5-yl)-1-ethanone | C14H18O | 详情 | 详情 | |
| (XI) | 60966 | 2-(2-isopropyl-2,3-dihydro-1H-inden-5-yl)-1-(4-morpholinyl)-1-ethanethione | C18H25NOS | 详情 | 详情 | |
| (XII) | 60967 | 2-(2-isopropyl-2,3-dihydro-1H-inden-5-yl)acetic acid | C14H18O2 | 详情 | 详情 | |
| (XIII) | 60968 | ethyl 2-(2-isopropyl-2,3-dihydro-1H-inden-5-yl)acetate | C16H22O2 | 详情 | 详情 | |
| (XIV) | 17470 | diethyl carbonate; diethylcarbonate | 105-58-8 | C5H10O3 | 详情 | 详情 |
| (XV) | 60969 | diethyl 2-(2-isopropyl-2,3-dihydro-1H-inden-5-yl)malonate | C19H26O4 | 详情 | 详情 | |
| (XVI) | 60970 | ethyl 2-(2-isopropyl-2,3-dihydro-1H-inden-5-yl)propanoate | C17H24O2 | 详情 | 详情 |