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【结 构 式】

【分子编号】37507

【品名】(1R,2S)-4-oxo-2-(3-phenylpropyl)cyclopentanecarboxylic acid

【CA登记号】

【 分 子 式 】C15H18O3

【 分 子 量 】246.30612

【元素组成】C 73.15% H 7.37% O 19.49%

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:(XV)

The decarboxylative hydrolysis of 2,4-dimethoxycarbonyl-3-(3-phenylpropyl)cyclopentanone (XIV) with HCl in acetic acid gives 4-carboxy-3-(3-phenylpropyl)cyclopentanone (XV), which by reaction with oxalyl chloride (B) is converted into the corresponding acyl chloride (XVI). The Arndt-Eistert carbon homologation in (XVI) with diazomethane and silver benzoate (C) in methanol affords 4-(methoxycarbonylmethyl)-4-(3-phenylpropyl)cyclopentanone (XVIIa), which is dehydrogenated by the sequence of reactions: N-bromosuccinimide and sodium selenofenolate (D) [to obtain intermediates (XVIIb) and (XVIIc), respectively], followed by reaction with hydrogen peroxide to give 4-(methoxycarbonylmethyl)-3-(3-phenylallyl)cyclopentanone (XVIIIa). Oxidation of (XVIIIa) first with osmium tetroxide and then with Jones reagent (CrO3) [to obtain intermediates (XVIIIb) and (XVIIIc), respectively], followed by methylation of (XVIIIc) with CH2N2 affords 3,4-di(methoxycarbonylmethyl)cyclopentanone (XIX), which is ketalized in the usual way to the ketal (XX). Finally, this compound is submitted to a Dieckmann condensation with sodium methoxide in DMS to yield the protected ketoester (IVa), the methyl ester analogue of the compound (IV) obtained in scheme 09083302a. This compound can then be used instead of (IV) in scheme 09083302a.

1 Sakai, K.; Kojima, K.; Synthetic studies of prostanoids. XVII. Total synthesis of 9(O)-methanoprostacyclin and its isomers. Tetrahedron Lett 1978, 39, 3743-46.
2 Castaner, J.; Hillier, K.; Carbacyclin. Drugs Fut 1981, 6, 12, 753.
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) 11295 Polyethylene glycol;1,2-Ethanediol;Monoethylene glycol; Ethylene glycol 107-21-1 C2H6O2 详情 详情
(IVa) 11312 (3'aS,4'R,6'aS)-5'-Oxoperhydrospiro[1,3-dioxolane-2,2'-pentalen]-4'-ylcarboxylic acid methyl ester C12H16O5 详情 详情
(XVIIa) 24518 methyl 2-[(1S,2S)-4-oxo-2-(3-phenylpropyl)cyclopentyl]acetate C17H22O3 详情 详情
(XVIIIa) 24519 methyl 2-[(1S,2S)-4-oxo-2-[(E)-3-phenyl-2-propenyl]cyclopentyl]acetate C17H20O3 详情 详情
(B) 29841 Oxalyl chloride; 2-Chloro-2-oxoacetyl chloride 79-37-8 C2Cl2O2 详情 详情
(XVIIb) 37510 methyl 2-[(1S,2S)-2-(3-bromo-3-phenylpropyl)-4-oxocyclopentyl]acetate C17H21BrO3 详情 详情
(D) 37511 sodium benzeneselenolate C6H5NaSe 详情 详情
(XVIIc) 37512 methyl 2-[(1S,2S)-4-oxo-2-[3-phenyl-3-(phenylselanyl)propyl]cyclopentyl]acetate C23H26O3Se 详情 详情
(XVIIIb) 37513 methyl 2-[(1S,2S)-4-oxo-2-(2-oxoethyl)cyclopentyl]acetate C10H14O4 详情 详情
(XVIIIc) 37514 2-[(1R,2S)-2-(2-methoxy-2-oxoethyl)-4-oxocyclopentyl]acetic acid C10H14O5 详情 详情
(XIV) 37506 dimethyl (1R,2R,3S)-4-oxo-2-(3-phenylpropyl)-1,3-cyclopentanedicarboxylate C18H22O5 详情 详情
(XV) 37507 (1R,2S)-4-oxo-2-(3-phenylpropyl)cyclopentanecarboxylic acid C15H18O3 详情 详情
(XVI) 37508 (1R,2S)-4-oxo-2-(3-phenylpropyl)cyclopentanecarbonyl chloride C15H17ClO2 详情 详情
(XIX) 24520 methyl 2-[(1R,2S)-2-(2-methoxy-2-oxoethyl)-4-oxocyclopentyl]acetate C11H16O5 详情 详情
(XX) 24521 methyl 2-[(7R,8S)-8-(2-methoxy-2-oxoethyl)-1,4-dioxaspiro[4.4]non-7-yl]acetate C13H20O6 详情 详情
(C) 37509 silver(1+) benzoate 532-31-0 C7H5AgO2 详情 详情
Extended Information