cis-2-tert-Butylcyclohexanol

Base Information

• Chemical Name: cis-2-tert-Butylcyclohexanol
• CAS No.: 13492-06-3
• Deprecated CAS: 67738-24-3
• Molecular Formula: C₁₀H₂₀O
• Molecular Weight: 156.268
• European Community (EC) Number: 230-601-5
• UNII: AI3Y3W3599,A236YP4EMC
• DSSTox Substance ID: DTXSID901269862
• Nikkaji Number: J221.595K
• Wikidata: Q27273932
• Mol file: 13492-06-3.mol

Synonyms:cis-2-tert-Butylcyclohexanol;Cyclohexanol, 2-tert-butyl-, cis-;(1S,2S)-2-tert-butylcyclohexan-1-ol;A236YP4EMC;2-tert-Butylcyclohexanol, cis-;AI3Y3W3599;7214-18-8;(+)-(1S,2S)-2-tert-Butylcyclohexanol;Cyclohexanol, 2-tert-butyl-, (+)-cis-;J221.595K;13492-06-3;Cyclohexanol, 2-(1,1-dimethylethyl)-, cis-(+)-;Cyclohexanol, 2-(1,1-dimethylethyl)-, (1S,2S)-;Cyclohexanol, 2-(1,1-dimethylethyl)-, cis-;UNII-AI3Y3W3599;Cyclohexanol, 2-(1,1-dimethylethyl)-, (1R,2R)-rel-;EINECS 230-601-5;NSC 108293;NSC-108293;UNII-A236YP4EMC;SCHEMBL6229389;DTXSID901269862;AKOS015914476;J231.562I;(1S)-2alpha-tert-Butylcyclohexane-1alpha-ol;(1S,2S)-2-(1,1-Dimethylethyl)cyclohexanol;2alpha-(1,1-Dimethylethyl)cyclohexan-1alpha-ol;Q27273932;REL-(1R*,2R*)-2-TERT-BUTYL-1-CYCLOHEXANOL;2.ALPHA.-(1,1-DIMETHYLETHYL)CYCLOHEXAN-1.ALPHA.-OL

Chemical Property of cis-2-tert-Butylcyclohexanol

Chemical Property:

• XLogP3: 3
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 1
• Exact Mass: 156.151415257
• Heavy Atom Count: 11
• Complexity: 123

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC(C)(C)C1CCCCC1O
• Isomeric SMILES: CC(C)(C)[C@@H]1CCCC[C@@H]1O

Technology Process of cis-2-tert-Butylcyclohexanol

There total 7 articles about cis-2-tert-Butylcyclohexanol which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

(-)-2-tert-butylcyclohexanone (14132-21-9) → (S,S)-cis-2-tert-butylcyclohexanol (13492-06-3) + (+)-(1S,2R)-2-(tert-butyl)cyclohexanol (13492-07-4)

Guidance literature:

With C₂₈H₃₅ClCoN₅⁽¹⁺⁾*Cl^(1-); potassium tert-butylate; hydrogen; In tetrahydrofuran; at 60 ℃; for 16h; under 37503.8 Torr; Overall yield = 94 %; stereoselective reaction; Autoclave;

DOI:10.1016/j.chempr.2019.03.010

Reference yield:

cis-2-tert-butylcyclohexanol (7214-18-8) → (S,S)-cis-2-tert-butylcyclohexanol (13492-06-3)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 37.6 percent / 1,10-phenanthroline / Pd(OAc)2 / 46 h / 60 °C

2.1: H₂O / chiral Co complex / methanol / 11 h / 20 °C

2.2: H₂O / PdCl₂(MeCN)2

With 1,10-Phenanthroline; water; palladium diacetate; chiral Co; In methanol;

DOI:10.1021/ol036228j

Reference yield:

2-tert-butylcyclohexanone (1728-46-7) → (S,S)-cis-2-tert-butylcyclohexanol (13492-06-3)

Guidance literature:

Multi-step reaction with 3 steps

1: 1.) BuLi / 1) THF, hexane, 0 deg C, 20 min; 2) THF, hexane, -78 deg C, 40 min

2: 95 percent / 0.33 h / 135 °C / 1 Torr

3: LiAlH₄ / diethyl ether / 1) 0 deg C, 2 h; 2) room temperature, 20 min

With lithium aluminium tetrahydride; n-butyllithium; In diethyl ether;

upstream raw materials:

(-)-2-tert-butylcyclohexanone

cis-2-tert-butylcyclohexanol

2-tert-butylcyclohexanone

(1S,2S,S_S)-2-tert-butyl-1-(N-tert-butyldiphenylsilyl-S-phenylsulfonimidoylmethyl)cyclohexanol

Downstream raw materials:

(-)-2-tert-butylcyclohexanone

Refernces

• 1、 Boyd,Sharma,Berberian,Dunne,Hardacre,Kaik,Kelly,Malone,McGregor,Stevenson. "Synthesis and reactions of enantiopure substituted benzene cis-hexahydro-1,2-diols". experimental part. p. 855 - 868. Retrieved 2010/07/05.
• 2、 Pyne, Stephen G.,Dong, Zemin,Skelton, Brian W.,White, Allan H.. "Chiral Sulfur Compounds. Part 25. Diastereoselective 1,2-Additions of Lithiated (+)-(S)-N-tert-Butyldiphenylsilyl-S-methyl-S-phenylsulfoximine to Ketones". . p. 2607 - 2614. Retrieved 2007/10/02.