28835-98-5Relevant academic research and scientific papers
ENANTIOSELECTIVE DEHYDROHALOGENATION VIA ASYMMETRIC DEPROTONATION BY CHIRAL LITHIUM AMIDES: DERACEMIZATION OF A COMPOUND BEARING A CHIRAL AXIS
Duhamel, Lucette,Ravard, Alain,Plaquevent, Jean-Christophe,Davoust, Daniel
, p. 5517 - 5520 (1987)
Chiral lithium amides exert asymmetric induction in dehydrohalogenation reactions leading to axially dissymmetric compounds.Thus the deracemization of 4-tert-butyl-cyclohexylidene acetic acid 1 via the prochiral hydrochlorinated intermediate 2 is reported
A New, General Cyclopentenone Synthesis
Ceccherelli, Paolo,Curini, Massimo,Marcotullio, Maria Carla,Rosati, Ornelio,Wenkert, Ernest
, p. 311 - 315 (2007/10/02)
A new synthesis of cyclopentenones, involving an Rh(II)-catalyzed, intramolecular carbon-hydrogen insertion of diazomethyl ketones derived from α,β-unsaturated acids, is described.
Deracemization by enantioselective dehydrohalogenation. Synthesis of optically active compounds bearing a chiral axis.
Duhamel, L.,Ravard, A.,Plaquevent, J. C.,Ple, G.,Davoust, D.
, p. 787 - 797 (2007/10/02)
This work describes the deracemization of 4-tert-butyl and 4-methylcyclohexylidene acetic acids bearing a chiral axis.Enantioselective dehydrohalogenation of prochiral species by chiral lithium amides allowed us to obtain e.e. as high as 82percent.A mecha
SYNTHESIS OF CYCLOHEXYLALIPHATIC ACIDS AND THEIR PHARMACOLOGICAL PROPERTIES
Kuchar, Miroslav,Brunova, Bohumila,Grimova, Jaroslava,Vanecek, Stanislav,Holubek, Jiri
, p. 2896 - 2908 (2007/10/02)
A series of substituted cyclohexylacetic acids I has been obtained by hydrogenation of the unsaturated analogues II and III.Esters of these analogues were prepared by the Horner-Wittig reaction of the corresponding cyclohexanones IV and/or 2-cyclohexenones V with triethyl phosphonoacetate.These esters were obtained in two isomeric forms (Z and E), differing in the double bond in the exo-position.The derivatives with a substituent in the 2-position exhibited a partial shift of the double bond to the cyclohexane ring; this shift was especially marked in the 2-phenyl derivative.With the acids I-III, activation of fibrinolysis was assessed by the hanging clot method; the anti-inflammatory effect was assessed by inhibition of two experimental model inflammations.The regression equation relating fibrinolytic capacity to lipophilicity was a quadratic one, the logarithm of optimum lipophilicity being log Popt = 5.55.A qualitative assessment of the anti-inflammatory effect in relation to lipophilicity suggests that log Popt is probably higher than with arylaliphatic acids.These acids seem to have an active site different from that of the acids I-III.
