Trans-2-Phenyl-1-cyclohexanol

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

trans-2-Phenyl-1-cyclohexanol

(1S,2R)-2-Phenylcyclohexanol
Names
Other names trans-2-Phenylcyclohexanol
Identifiers
CAS Number	(±): 2362-61-0 Y (−)-(1R,2S): 98919-68-7 Y (+)-(1S,2R): 34281-92-0 Y
3D model (JSmol)	(+)-(1S,2R): Interactive image
ChemSpider	(+)-(1S,2R): 8074632 Y
PubChem CID	(+)-(1S,2R): 9898975
UNII	(±): 452WZ637M8 Y (−)-(1R,2S): O5411L8484 Y (+)-(1S,2R): D2U0RW1Y61 Y
CompTox Dashboard (EPA)	DTXSID30432512
InChI (+)-(1S,2R): 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 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
SMILES (+)-(1S,2R): O[C@@H]2[C@@H](c1ccccc1)CCCC2
Properties
Chemical formula	C12H16O
Molar mass	176.259 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). N verify (what is YN ?) Infobox references

Preparation

The enantioselective synthesis was accomplished by J. K. Whitesell by adding Pseudomonas fluorescens lipase to racemic trans-2-phenylcyclohexyl chloroacetate.^[1][2] 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.^[3]

trans-2-Phenyl-1-hexanol enantiomers in chair conformations