trans-2-Phenyl-1-cyclohexanol

*trans*-2-Phenyl-1-cyclohexanol
	; (1S,2R)-2-Phenylcyclohexanol
Names
	Other names trans-2-Phenylcyclohexanol
Identifiers
CAS Number	(±): 2362-61-0 ; (−)-(1R,2S): 98919-68-7 ; (+)-(1S,2R): 34281-92-0 ;
3D model (JSmol)	(+)-(1S,2R): Interactive image;
ChemSpider	(+)-(1S,2R): 8074632 ;
PubChem CID	(+)-(1S,2R): 9898975;
UNII	(±): 452WZ637M8 ; (−)-(1R,2S): O5411L8484 ; (+)-(1S,2R): D2U0RW1Y61 ;
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 Key: AAIBYZBZXNWTPP-NEPJUHHUSA-N ;
	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). verify (what is ?) 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.

Preparation[edit]

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

References[edit]

^ J. K. Whitesell, H. H. Chen and R. M. Lawrence (1985). "trans-2-Phenylcyclohexanol. A powerful and readily available chiral auxiliary". J. Org. Chem. 50 (23): 4663–4664. doi:10.1021/jo00223a055.
^ A. Schwartz, P. Madan, J. K. Whitesell, and R. M. Lawrence (1993). "Lipase-Catalyzed Kinetic Resolution of Alcohols via Chloroacetate Esters: (−)-(1R,2S)-Trans-2-Phenylcyclohexanol And (+)-(1S,2R)-Trans-2-Phenylcyclohexanol". Organic Syntheses{{cite journal}}: CS1 maint: multiple names: authors list (link); Collected Volumes, vol. 8, p. 516.
^ Javier Gonzalez, Christine Aurigemma, and Larry Truesdale (2004). "Sharpless bishydroxylation procedure to trans-2-phenyl-1-cyclohexanol". Organic Syntheses{{cite journal}}: CS1 maint: multiple names: authors list (link); Collected Volumes, vol. 10, p. 603.

[1] J. K. Whitesell, H. H. Chen and R. M. Lawrence (1985). "trans-2-Phenylcyclohexanol. A powerful and readily available chiral auxiliary". J. Org. Chem. 50 (23): 4663–4664. doi:10.1021/jo00223a055.

[2] A. Schwartz, P. Madan, J. K. Whitesell, and R. M. Lawrence (1993). "Lipase-Catalyzed Kinetic Resolution of Alcohols via Chloroacetate Esters: (−)-(1R,2S)-Trans-2-Phenylcyclohexanol And (+)-(1S,2R)-Trans-2-Phenylcyclohexanol". Organic Syntheses{{cite journal}}: CS1 maint: multiple names: authors list (link); Collected Volumes, vol. 8, p. 516.

[3] Javier Gonzalez, Christine Aurigemma, and Larry Truesdale (2004). "Sharpless bishydroxylation procedure to trans-2-phenyl-1-cyclohexanol". Organic Syntheses{{cite journal}}: CS1 maint: multiple names: authors list (link); Collected Volumes, vol. 10, p. 603.

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