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【结 构 式】

【分子编号】12991

【品名】1-[(3-Methyl-2-butenyl)sulfanyl]benzene; 3-Methyl-2-butenyl phenyl sulfide

【CA登记号】

【 分 子 式 】C11H14S

【 分 子 量 】178.29816

【元素组成】C 74.1% H 7.91% S 17.98%

与该中间体有关的原料药合成路线共 1 条

合成路线1

该中间体在本合成路线中的序号:(III)

The condensation of thiophenol (II) with 3-methyl-2-butenyl bromide (I) by means of NaOH in refluxing acetone gives 3-methyl-2-butenyl(phenyl)sulfide (III), which is cyclized by means of P2O5 and H3PO4 in refluxing benzene to yield 4,4-dimethyl-3,4-dihydro-1H-1-benzothiopyran (IV). The acylation of (IV) with acetyl chloride catalyzed by SnCl4 in benzene affords the corresponding 6-acetyl derivative (V), which by dehydration with lithium diisopropylamide and diethyl chlorophosphate in THF is converted into 6-ethynyl-4,4-dimethyl-3,4-dihydro-2H-1-benzothiopyran (VI). Finally, this compound is condensed with ethyl 6-chloropyridine-3-carboxylate (VII) by means of butyllithium in THF. The ester (VII) is obtained by esterification of the corresponding acid (VIII) with ethanol by means of dicyclohexylcarbodiimide (DCC) and dimethylaminopyridine (DMAP).

1 Ngo, J.; Leeson, P.A.; Castaner, J.; Tazarotene. Drugs Fut 1997, 22, 3, 249.
2 Chandraratna, R.A.S. (Allergan, Inc.); Disubstd. acetylenes bearing heteroaromatic and heterobicyclic groups having retinoid like activity. EP 0284288; JP 88255277; JP 95324085 .
3 Chandraratna, R.A.S. (Allergan, Inc.); Disubstd. acetylenes bearing heteroaromatic and heterobicyclic groups having retinoid like activity. US 5089509 .
4 Chandraratna, R.A. (Allergan, Inc.); Disubstd. acetylenes bearing heteroaromatic and heterobicyclic groups having retinoid like activity. WO 9611686 .
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) 12989 4-Bromo-2-methyl-2-butene; 1-Bromo-3-methyl-2-butene 870-63-3 C5H9Br 详情 详情
(II) 12951 Benzenethiol; Phenylmercaptan; Phenylhydrosulfide 108-98-5 C6H6S 详情 详情
(III) 12991 1-[(3-Methyl-2-butenyl)sulfanyl]benzene; 3-Methyl-2-butenyl phenyl sulfide C11H14S 详情 详情
(IV) 12992 4,4-Dimethylthiochromane C11H14S 详情 详情
(V) 12993 1-(4,4-Dimethyl-3,4-dihydro-2H-thiochromen-6-yl)-1-ethanone C13H16OS 详情 详情
(VI) 12994 6-Ethynyl-4,4-dimethylthiochromane C13H14S 详情 详情
(VII) 12995 ethyl 6-chloronicotinate 49608-01-7 C8H8ClNO2 详情 详情
(VIII) 12996 6-Chloronicotinic acid 5326-23-8 C6H4ClNO2 详情 详情
Extended Information