• English
  • 简体中文
Login Register
Current Location: Home > Feedback Help Print

【结 构 式】

【分子编号】54406

【品名】2-Methylcyclohexanone; Tetrahydro-o-cresol; o-Methylcyclohexanone

【CA登记号】583-60-8

【 分 子 式 】C7H12O

【 分 子 量 】112.17168

【元素组成】C 74.95% H 10.78% O 14.26%

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:(I)

The condensation of 2-methylcyclohexanone (I) with 2-thienyl lithium (II) or 2-thienylmagnesium bromide (III) gives cyclohexanol (IV) as a diastereomeric mixture, which was treated with Na-N3 in trichloroacetic acid to yield the azide (V). The reduction of (V) with LiAlH4 or RaNi/iPr-OH affords the corresponding amine (VI), preferentially with the cis-configuration. Finally, this compound is condensed with 1,5-dibromopentane (VII) by means of K2CO3 in acetonitrile to provide the target compound as a diastereomeric mixture. The separation of the cis- and trans- racemates has been performed by HPLC. The optical resolution was performed by a cumbersome crystallization process using CSA and di-p-toluoyltartaric acid.

1 Michaud, M.; et al.; Homochiral structures derived from 1-[1-(2-thienyl)cyclohexyl]piperidine (TCP) are potent non-competitive antagonists of glutamate at NMDA receptor sites. Eur J Med Chem 1994, 29, 11, 869.
2 Kamenka, J.-M.; Privat, A.; Chicheportiche, R.; Rondouin, G. (CNRS (Centre National de la Recherche Scientifique)); Pharmaceutical compsns. for neuroprotection containing arylcyclohexylamines. US 5179109; WO 9005524 .
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) 54406 2-Methylcyclohexanone; Tetrahydro-o-cresol; o-Methylcyclohexanone 583-60-8 C7H12O 详情 详情
(II) 21682 2-thienyllithium 2786-07-4 C4H3LiS 详情 详情
(III) 32082 bromo(2-thienyl)magnesium 5713-61-1 C4H3BrMgS 详情 详情
(IV) 54407 (1R,2S)-2-methyl-1-(2-thienyl)cyclohexanol C11H16OS 详情 详情
(V) 54408 (1R,2S)-2-methyl-1-(2-thienyl)cyclohexyl azide; 2-[(1R,2S)-1-azido-2-methylcyclohexyl]thiophene C11H15N3S 详情 详情
(VI) 54409 (1R,2S)-2-methyl-1-(2-thienyl)cyclohexanamine; (1R,2S)-2-methyl-1-(2-thienyl)cyclohexylamine C11H17NS 详情 详情
(VII) 30560 1,5-dibromopentane 111-24-0 C5H10Br2 详情 详情
Extended Information