Trans-2-Phenyl-1-cyclohexanol

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


Wikimedia Foundation. 2010.

Игры ⚽ Нужно решить контрольную?

Look at other dictionaries:

  • Chiral auxiliary — A chiral auxiliary is a chemical compound or unit that is temporarily incorporated into an organic synthesis so that it can be carried out asymmetrically with the selective formation of one of two enantiomers[1][2] . Chiral auxiliaries are… …   Wikipedia

  • Ojima lactam — The Ojima lactam is an organic compound of some importance in the commercial production of Taxol. This lactam was first synthesized by Iwao Ojima [1]. The organic synthesis is an illustration of asymmetric synthesis via a chiral auxiliary. The… …   Wikipedia

  • Chemikalienliste — Die Chemikalienliste stellt eine alphabetisch sortierte Liste von Chemikalien dar, ohne Anspruch auf Vollständigkeit. Elemente sind fett gekennzeichnet, Stoffgruppen kursiv. Der Haupteintrag zu einer Chemikalie ist gleichzeitig der Name des… …   Deutsch Wikipedia

  • Liste chemischer Verbindungen — Die Chemikalienliste stellt eine alphabetisch sortierte Liste von Chemikalien dar, ohne Anspruch auf Vollständigkeit. Elemente sind fett gekennzeichnet, Stoffgruppen kursiv. Der Haupteintrag zu einer Chemikalie ist gleichzeitig der Name des… …   Deutsch Wikipedia

  • Liste von chemischen Verbindungen — Die Chemikalienliste stellt eine alphabetisch sortierte Liste von Chemikalien dar, ohne Anspruch auf Vollständigkeit. Elemente sind fett gekennzeichnet, Stoffgruppen kursiv. Der Haupteintrag zu einer Chemikalie ist gleichzeitig der Name des… …   Deutsch Wikipedia

  • Dicarboxylic acid — Dicarboxylic acids are organic compounds that contain two carboxylic acid functional groups. In molecular formulae for dicarboxylic acids, these groups are often written as HOOC R COOH, where R may be an alkyl, alkenyl, alkynyl, or aryl group.… …   Wikipedia

  • List of organic compounds — This page aims to list well known organic compounds, including organometallic compounds, to stimulate the creation of Wikipedia articles. Note that purely inorganic compounds, minerals, and chemical elements are not included on this list. There… …   Wikipedia

Share the article and excerpts

Direct link
Do a right-click on the link above
and select “Copy Link”