Key indicators: single-crystal X-ray study; T = 296 K; mean (C-C) = 0.003 Å; disorder in main residue; R factor = 0.053; wR factor = 0.141; data-to-parameter ratio = 17.7.The title compound, C 20 H 26 O 6 , is chiral and crystallizes as a racemate: the relative configuration of the stereogenic centres is 1R*,2R*,3S*,4R*. The cyclohexane ring has a chair conformation. The ethyl fragment of the ethoxycarbonyl group in the 3-position is disordered over two sets of sites in a 0.650 (6):0.350 (6) ratio. The hydroxy group acts as a bifurcated hydrogen-bond donor, forming both intra-and intermolecular hydrogen bonds with ester carbonyl O atoms. The intermolecular hydrogen bonds form inversion dimers in the crystal.
Related literatureFor applications of related compounds as synthetic intermediates, see: Gein et al. (2003Gein et al. ( , 2004 Sorokin et al. (2000).
ExperimentalCrystal data
The title compound, C18H22N2O3, represents a (4S,5R,6S)-stereoisomer, crystallizing as a racemate in a centrosymmetric space group. The six-membered aliphatic ring adopts a half-chair conformation, with the hydroxy- and acetyl-substituted C atoms deviating by 0.458 (2) and −0.366 (2) Å, respectively, from the plane defined by other four ring atoms. The pyrazole ring is essentially planar [r.m.s deviation = 0.004 (2) Å]. In the crystal, the molecules are linked into chains along the b axis by N—H⋯N hydrogen bonds. The chains are linked by O—H⋯N hydrogen bonds into layers parallel to the bc plane.
Three-component condensation reaction of malonodinitrile, 4-chloro-benzaldehyde and ethyl 4chloro-3-oxobutanoate has been analyzed to establish that in the presence of NaOH base, the reaction proceeds by Knoevenagel-Michael-Perkin cascade carbocyclization to form ethyl-1acetyl-3-(4-chlorophenyl)-2,2-dicyanocyclopropane carboxylate. The structure of the reaction product examined through with X-ray analysis
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