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【结 构 式】

【分子编号】53409

【品名】2-chloro-2-cyclohexen-1-one

【CA登记号】n/a

【 分 子 式 】C6H7ClO

【 分 子 量 】130.57368

【元素组成】C 55.19% H 5.4% Cl 27.15% O 12.25%

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:(XXII)

Treatment of 2-cyclohexenone (XXI) with SO2Cl2 and 2,6-lutidine in dichloromethane provides 2-chloro-2-cyclohexenone (XXII), which is reduced with (S)-tetrahydro-1-methyl-3,3-diphenyl-1H,3H-pyrrolo[1,2-c][1,3,2]-oxazaborole and borane dimethyl sulfide complex in THF/MeOH giving (R)-2-chloro-2-cyclohexen-1-ol (XXIII). Reaction of (XXIII) with trichloroacetonitrile by means of NaH in diethyl ether gives the cyclohexenol derivative (XXIV), which is converted into acetamide (XXV) by heating at 140 C in chlorobenzene. Hydrolysis of (XXV) with K2CO3 in water/methanol affords (S)-2-chloro-2-cyclohexen-1-amine (XXVI), which is then condensed with N-phthaloyl-L-phenylalanine acid chloride (VI) in ethyl acetate to yield amide (XXVII). Finally, ozonolysis of amide (XXVII) in CH2Cl2/MeOH, followed by reduction with tributylphosphine and treatment with TFA in refluxing CH2Cl2 provides the previously described intermediate (XII).

1 del Fresno, M.; Bayes, M.; Castaner, R.M.; Sorbera, L.A.; MDL-100240. Drugs Fut 2002, 27, 5, 458.
2 Flynn, G.A. (Merrell Pharmaceuticals, Inc.); Novel process for preparing (S)-1-[2(S)-(1,3-dihydro-1,3-dioxo-isoindo-2-yl)-1-oxo-3-phenylpropyl]-1,2,3,4-tetrahydro-2-pyridine-carboxylic acid methyl ester and intermediates thereof. WO 9514663 .
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
28292 (S)-Methyl oxazaborolidine; (3aS)-1-methyl-3,3-diphenyltetrahydro-3H-pyrrolo[1,2-c][1,3,2]oxazaborole 112022-81-8 C18H20BNO 详情 详情
(VI) 52756 (2S)-2-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)-3-phenylpropanoyl chloride C17H12ClNO3 详情 详情
(XII) 37296 methyl (2S)-1-[(2S)-2-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)-3-phenylpropanoyl]-1,2,3,4-tetrahydro-2-pyridinecarboxylate C24H22N2O5 详情 详情
(XXI) 26253 2-cyclohexen-1-one;Cyclohex-2-enone;2-cyclohexenone 930-68-7 C6H8O 详情 详情
(XXII) 53409 2-chloro-2-cyclohexen-1-one n/a C6H7ClO 详情 详情
(XXIII) 53410 (1R)-2-chloro-2-cyclohexen-1-ol n/a C6H9ClO 详情 详情
(XXIV) 53411 (1R)-2-chloro-2-cyclohexen-1-yl 2,2,2-trichloroethanimidoate n/a C8H9Cl4NO 详情 详情
(XXV) 53412 2,2,2-trichloro-N-[(1S)-2-chloro-2-cyclohexen-1-yl]acetamide n/a C8H9Cl4NO 详情 详情
(XXVI) 53413 (1S)-2-chloro-3-cyclohexen-1-amine; (1S)-2-chloro-3-cyclohexen-1-ylamine n/a C6H10ClN 详情 详情
(XXVII) 53414 (2S)-N-[(1S)-2-chloro-3-cyclohexen-1-yl]-2-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)-3-phenylpropanamide n/a C23H21ClN2O3 详情 详情
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