4272-03-1

Upstream product

• 40541-50-2 α-cyclohexyl-γ-butyrolactone 
• 40745-21-9 dimethyl 2-cyclohexylidenesuccinate 
• 1122-60-7 1-nitrocyclohexane 
• 75354-08-4 2-Cyclohexylbutandisaeure-diethylester 
• 5452-75-5 ethyl 2-cyclohexylacetate 

Relevant academic research and scientific papers

Synthesis and stereochemical assignment of geraniol- and nerol-derived Cygerol enantiomers

The enantiomers (up to 99% ee) of both geraniol- and nerol-derived 2-cyclohexyl-5,9-dimethyldeca-4,8-dienoic acid, the active ingredient of the wound healing medication Cygerol, were prepared via a low-temperature alkylation, basic hydrolysis, derivatization with (S)-4-benzyloxazolidin-2-one and chromatographic separation steps. The absolute configuration of stereocenters in the antipodes having an (E)- or (Z)-geometry of the internal double bond was determined based on characteristic 1H NMR signals of the corresponding (S)-4-benzyloxazolidin-2-one-derived imides and on conversion to the known diethyl (S)-2-cyclohexylsuccinate and (S)-2-cyclohexylbutane-1,4-diol with reported specific rotations.

Nitroalkanes as a new source of 2-alkylidene-1,4-diols, in two steps

A variety of 2-alkylidene-1,4-diols have been conveniently prepared, in two steps, by conjugate addition of a nitroalkane to the appropriate enedione derivatives under basic conditions (DBU), followed by chemoselective reduction (LiAlH4/Et2O) of the carbonyl functionalities of the Michael adduct, obtained after elimination of nitrous acid.