| Revision as of 13:49, 10 January 2012 editBeetstra (talk | contribs)Edit filter managers, Administrators172,084 edits Saving copy of the {{chembox}} taken from revid 401640785 of page Trans-2-Phenyl-1-cyclohexanol for the Chem/Drugbox validation project (updated: 'CASNo'). |
Latest revision as of 21:57, 15 January 2021 edit Fswitzer4 (talk | contribs)Extended confirmed users11,001 editsm Corrected CAS |
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{{DISPLAYTITLE:''trans''-2-Phenyl-1-cyclohexanol}} |
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{{ambox | text = This page contains a copy of the infobox ({{tl|chembox}}) taken from revid of page ] with values updated to verified values.}} |
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{{chembox |
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{{chembox |
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| Name = ''trans''-2-Phenyl-1-cyclohexanol |
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| verifiedrevid = 401639290 |
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| Verifiedfields = changed |
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|Name = (1''S'',2''R'')-2-phenylcyclohexanol |
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| Watchedfields = changed |
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|ImageFile=(1S,2R)-2-phenylcyclohexanol-2D-skeletal.png |
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| verifiedrevid = 470612367 |
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|ImageSize= |
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|IUPACName=(1S,2R)-2-phenyl-1-cyclohexanol |
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| ImageFile=(1S,2R)-2-phenylcyclohexanol-2D-skeletal.png |
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| ImageCaption = (1''S'',2''R'')-2-Phenylcyclohexanol |
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|OtherNames= |
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| IUPACName= |
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| OtherNames=''trans''-2-Phenylcyclohexanol |
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|Section1={{Chembox Identifiers |
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|Section1={{Chembox Identifiers |
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| index1_label = (±) |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| index2_label = (−)-(1''R'',2''S'') |
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| ChemSpiderID = 8074632 |
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| index3_label = (+)-(1''S'',2''R'') |
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| 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 |
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| ChemSpiderID3_Ref = {{chemspidercite|correct|chemspider}} |
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| InChIKey = AAIBYZBZXNWTPP-NEPJUHHUBI |
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| ChemSpiderID3 = 8074632 |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChI = 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 |
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| InChI3 = 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 |
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| InChIKey3 = AAIBYZBZXNWTPP-NEPJUHHUBI |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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| InChI4_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChIKey = AAIBYZBZXNWTPP-NEPJUHHUSA-N |
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| InChI4 = 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 |
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| CASNo = <!-- blanked - oldvalue: 34281-92-0 --> |
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| InChIKey4_Ref = {{stdinchicite|correct|chemspider}} |
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| PubChem=9898975 |
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| InChIKey4 = AAIBYZBZXNWTPP-NEPJUHHUSA-N |
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| SMILES = O2(c1ccccc1)CCCC2 |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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| CASNo1 = 2362-61-0 |
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| CASNo1_Ref = {{cascite|correct|CAS}} |
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| CASNo2 = 98919-68-7 |
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| CASNo2_Ref = {{cascite|correct|CAS}} |
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| CASNo3 = 34281-92-0 |
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| CASNo3_Ref = {{cascite|correct|CAS}} |
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| UNII1 = 452WZ637M8 |
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| UNII1_Ref = {{fdacite|correct|FDA}} |
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| UNII2 = O5411L8484 |
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| UNII2_Ref = {{fdacite|correct|FDA}} |
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| UNII3 = D2U0RW1Y61 |
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| UNII3_Ref = {{fdacite|correct|FDA}} |
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| PubChem3=9898975 |
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| SMILES3 = O2(c1ccccc1)CCCC2 |
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}} |
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|Section2={{Chembox Properties |
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|Section2={{Chembox Properties |
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| C=12|H=16|O=1 |
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| C=12 | H=16 | O=1 |
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|Section3={{Chembox Hazards |
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'''''trans''-2-Phenyl-1-cyclohexanol''' is an ]. The two ]s of this compound are used in ] as ]. |
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==Preparation== |
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The ] synthesis was accomplished by J. K. Whitesell by adding '']'' ] to ] ''trans''-2-phenylcyclohexyl chloroacetate.<ref>{{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 = ] | volume = 50 | issue = 23 | pages = 4663–4664 | doi = 10.1021/jo00223a055}}</ref><ref>{{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}}</ref> This ] is able to ] the ] bond of the (−)-enantiomer but not the (+)-enantiomer. The (−)-cyclohexanol and the (+)-ester are separated by ] and the isolated (+)-ester hydrolyzed to the (+)-cyclohexanol in a separate step. |
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The enantiomers have also been prepared by the ] of 1-phenylcyclohexene to the ] followed by the selective ] of the 1-hydroxyl group by ].<ref>{{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}}</ref> |
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]]]{{clear-left}} |
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== References == |
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{{reflist}} |
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{{DEFAULTSORT:Phenyl-1-hexanol, trans-2-}} |
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] |
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] |