Trans-2-Phenyl-1-cyclohexanol

chembox new
Name = (1"S",2"R")-2-phenylcyclohexanol
ImageFile=(1S,2R)-2-phenylcyclohexanol-2D-skeletal.pngImageSize=
IUPACName=(1S,2R)-2-phenyl-1-cyclohexanol
OtherNames=
Section1=Chembox Identifiers
CASNo=
PubChem=9898975
SMILES=C1CCC(C(C1)C2=CC=CC=C2)O
Section2=Chembox Properties
Formula=C₁₂H₁₆O
MolarMass=176.25484
Appearance=
Density=
MeltingPt=
BoilingPt=
Solubility=
Section3=Chembox Hazards
MainHazards=
FlashPt=
Autoignition=

"trans"-2-Phenyl-1-cyclohexanol is an organic compound. The two enantiomers of this compound are used in organic chemistry as chiral auxiliaries.

Preparation

The enantioselective synthesis was accomplished by J. K. Whitesell by adding Pseudomonas fluorescens lipase to racemic "trans"-2-phenylcyclohexyl chloroacetate. [cite journal | author = J. K. Whitesell, H. H. Chen and R. M. Lawrence | title = trans-2-Phenylcyclohexanol. A powerful and readily available chiral auxiliary | year = 1985 | journal = J. Org. Chem. | volume = 50 | issue = 23 | pages = 4663–4664 | doi = 10.1021/jo00223a055] [OrgSynth | collvol = 8 | collvolpages = 516 | year = 1993 | prep = cv8p0516 | title = Lipase-Catalyzed Kinetic Resolution of Alcohols via Chloroacetate Esters: (−)-(1R,2S)-Trans-2-Phenylcyclohexanol And (+)-(1S,2R)-Trans-2-Phenylcyclohexanol | author = A. Schwartz, P. Madan, J. K. Whitesell, and R. M. Lawrence] This enzyme is able to hydrolyze the ester bond of the (-) enantiomer but not the (+) enantiomer. The (-)-cyclohexanol and the (+)-ester are separated by fractional crystallization and the isolated (+)-ester hydrolyzed to the (-)-cyclohexanol in a separate step.

The enantiomers have also been prepared by the Sharpless asymmetric dihydroxylation of 1-phenylcyclohexene to the diol followed by the selective reduction of the 1-hydroxyl group by Raney nickel. [OrgSynth | title = Sharpless bishydroxylation procedure to "trans"-2-phenyl-1-cyclohexanol | collvol = 10 | collvolpages = 603 | year = 2004 | prep = V79P0093 | author = Javier Gonzalez, Christine Aurigemma, and Larry Truesdale]

chair conformations

References