Trans-2-phenyl-1-cyclohexanol

(1S,2R)-2-phenylcyclohexanol

Names
IUPAC name (1S,2R)-2-phenyl-1-cyclohexanol
Identifiers
CAS Number	34281-92-0 N
3D model (JSmol)	Interactive image
ChemSpider	8074632 Y
PubChem CID	9898975
InChI InChI=1S/C12H16O/c13-12-9-5-4-8-11(12)10-6-2-1-3-7-10/h1-3,6-7,11-13H,4-5,8-9H2/t11-,12+/m1/s1 Y Key: AAIBYZBZXNWTPP-NEPJUHHUSA-N Y InChI=1/C12H16O/c13-12-9-5-4-8-11(12)10-6-2-1-3-7-10/h1-3,6-7,11-13H,4-5,8-9H2/t11-,12+/m1/s1 Key: AAIBYZBZXNWTPP-NEPJUHHUBI
SMILES O[C@@H]2[C@@H](c1ccccc1)CCCC2
Properties
Chemical formula	C12H16O
Molar mass	176.26 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N  (what is YN ?)
Infobox references

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

The enantioselective synthesis was accomplished by J. K. Whitesell by adding Pseudomonas fluorescens lipase to racemic trans-2-phenylcyclohexyl chloroacetate. 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.