4-Ethoxycarbonyl-3-hydroxy-3-phenylcyclohexanone

Abstract

The title compound, ethyl 2-hydroxy-4-oxo-2-phenylcyclohexanecarboxylate, C(15)H(18)O(4), was obtained by a Michael-Aldol condensation and has the cyclohexanone in a chair conformation. The attached hydroxy, ethoxycarbonyl and phenyl groups are disposed in beta-axial, beta-equatorial and alpha-equatorial configurations, respectively. An intermolecular hydrogen bond, with an O.O distance of 2.874 (2) A, links the OH group and the ring carbonyl. Weak intermolecular C-H.O=C (ester and ketone), O-H.O=C (ketone) and C-H.OH hydrogen bonds exist.

2-[3-Furyl(hydroxy)methyl]-2,3-dimethylcyclohexanone

“…The C1( O1)ÐC2ÐC6 fragment of the cyclohexanone ring is practically planar, within experimental error [the maximum deviation from the plane is À0.020 (3) A Ê for atom C1], and the C1 O1 bond distance [1.227 (3) A Ê ] is within the normal range. Similar results were found in previously reported cyclohexanones (Barluenga et al, 1993;Brunner & Maas, 1995;Herna  ndez-Ortega et al, 2001;Rowland et al, 1998).…”

Synthesis of New Chiral 6-Carbonyl 2,3,8,8a-Tetrahydro-7H-oxazolo[3,2-a]pyridines

“…As reported in Table , the expected piperidines 2 were obtained in all cases in good to excellent yields, except when reacting tricarbonyl substrates 3h and 3j . In the case of the diketone 3h (Table , entries 15 and 16), the only product isolated after silica gel chromatography was racemic cyclohexanone 6 (Scheme ). Comparison of the physical and spectroscopic data for this compound with those reported in the literature 17 allowed to attribute a cis relative stereochemistry.…”