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【结 构 式】 
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【分子编号】23999 【品名】3-fluoro-8-isopropyldibenzo[b,f]thiepin-10(11H)-one 【CA登记号】 |
【 分 子 式 】C17H15FOS 【 分 子 量 】286.3699032 【元素组成】C 71.3% H 5.28% F 6.63% O 5.59% S 11.2% |
合成路线1
该中间体在本合成路线中的序号：(IV)The reaction of 2-bromo-4-fluorophenylacetic acid (I) with 4-isopropytthiophenol (II) by means of Cu and K2CO3 in DMF at 100 C gives 4-fluoro-2-(4-isopropylphenylthio)phenylacetic acid (III), which is cyclized by treatment with polyphosphoric acid at 1 500 yielding 3-fluoro-8-isopropyldibenzo[b,f]-thiepin-10(11H) one (IV). The reduction of (IV) with NaBH4 in ethanol affords 3-fluoro-10-hydroxy-8-isopropyl-10,11-dihydrodibenzo[b,f]thiepin (V), which is treated with SOCl2 refluxing benzene to give 10-chloro-3-fluoro-8-isopropyl-10,11-dihydro-dibenzo[b,f]thiepin (VI). Finally, this compound is condensed with 1-(2-hydroxyethyl)piperazine (VII) in refluxing CHCl3.
| 【1】 Protiva, M.; et al.; Fluorinated tricyclic neuroleptics with prolonged action: 7-Fluoro-11-[4-(2-hydroxyethyl)piperazino]-2-isopropyl-10,11-dihydrodibenzo[b,f]thiepin. M Coll Czech Chem Commun 1986, 51, Suppl. 2, 698. |
| 【2】 Jilek, J.; et al.; M Coll Czech Chem Commun 1984, 49, 2, 638. |
| 【3】 Dlabac, A.; Miksik, F.; Pomykacek, J.; Jilek, J.; Sindelar, K.; Rajsner, M.; Langsadl, L.; Metysova, J.; Bartl, V.; Protiva, M. (SPOFA - United Pharmaceutical Works); 3-Fluoro-10-piperazino-8-substituted 10,11-dihydrodibenzo(bf) thiepins and method for the preparation thereof. BE 0872496; DE 2855703; FR 2412312; GB 2010843; JP 7992979; US 4243805 . |
| 【4】 Castaner, J.; Prous, J.; Isofloxythepin. Drugs Fut 1986, 11, 7, 567. |
| 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) | 23996 | 2-(2-bromo-4-fluorophenyl)acetic acid | C8H6BrFO2 | 详情 | 详情 | |
| (II) | 23997 | 4-isopropylbenzenethiol | 4946-14-9 | C9H12S | 详情 | 详情 |
| (III) | 23998 | 2-[4-fluoro-2-[(4-isopropylphenyl)sulfanyl]phenyl]acetic acid | C17H17FO2S | 详情 | 详情 | |
| (IV) | 23999 | 3-fluoro-8-isopropyldibenzo[b,f]thiepin-10(11H)-one | C17H15FOS | 详情 | 详情 | |
| (V) | 24000 | 3-fluoro-8-isopropyl-10,11-dihydrodibenzo[b,f]thiepin-10-ol | C17H17FOS | 详情 | 详情 | |
| (VI) | 24001 | 11-chloro-7-fluoro-2-isopropyl-10,11-dihydrodibenzo[b,f]thiepine | C17H16ClFS | 详情 | 详情 | |
| (VII) | 24014 | Phenyllithium | 591-51-5 | C6H5Li | 详情 | 详情 |