(+/-)-Methyl and (+/-)-ethyl 4-(2,3-difluorophenyl)-2,6,6-trimethyl-5-oxo-1,4,5,6,7,8-hexahydroquinoline-3-carboxylate.
The title compounds, C20H21F2NO3 and C21H23F2NO3, respectively, belong to a class of 1,4-dihydropyridines whose members sometimes display calcium modulatory properties. The 1,4-dihydropyridine rings have the usual shallow boat conformation. In each structure, the 2,3-difluorophenyl ring is oriented such that the fluoro substituents are in a synperiplanar orientation with respect to the 1,4-dihydropyridine ring plane and the oxocyclohexene ring has a slightly distorted envelope conformation. Both structures exhibit the same intermolecular N-H...O hydrogen-bonding motif, in which the molecules are linked into chains by interactions involving the carbonyl O atom of the oxocyclohexene ring.
Linden
Anthony
A
Institute of Organic Chemistry, University of Zürich, Winterthurerstrasse 190, CH-8057 Zürich, Switzerland. alinden@oci.unizh.ch
Simşek
Rahime
R
Gündüz
Miyase
M
Safak
Cihat
C
D002121:Calcium Channel Blockers / Q000737:chemistry; D018360:Crystallography, X-Ray; D004095:Dihydropyridines / Q000737:chemistry*; D006860:Hydrogen Bonding; D008958:Models, Molecular; D008968:Molecular Conformation; D013237:Stereoisomerism
D002121:Calcium Channel Blockers; D004095:Dihydropyridines