(1S,2R,5S)-5-Methyl-2-(2-phenylpropan-2-yl)cyclohexanol

Base Information

• Chemical Name: (1S,2R,5S)-5-Methyl-2-(2-phenylpropan-2-yl)cyclohexanol
• CAS No.: 57707-91-2
• Molecular Formula: C16H24 O
• Molecular Weight: 232.366
• European Community (EC) Number: 634-672-7
• Nikkaji Number: J283.475H
• Mol file: 57707-91-2.mol

Synonyms:57707-91-2;SCHEMBL12159717;(1S,2R,5S)-5-Methyl-2-(2-phenylpropan-2-yl)cyclohexanol;(+)-8-Phenylmenthol, >=98.0% (sum of enantiomers, HPLC)

Chemical Property of (1S,2R,5S)-5-Methyl-2-(2-phenylpropan-2-yl)cyclohexanol

Chemical Property:

• Vapor Pressure: 5.55E-05mmHg at 25°C
• Refractive Index: n20/D 1.531
• Boiling Point: 333.1°C at 760 mmHg
• Flash Point: 138.2°C
• PSA: 20.23000
• Density: 0.999 g/mL at 20 °C(lit.)
• LogP: 3.76130
• Storage Temp.: 2-8°C
• XLogP3: 4.5
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 2
• Exact Mass: 232.182715385
• Heavy Atom Count: 17
• Complexity: 240

Purity/Quality:

99% ^*data from raw suppliers

(+)-8-Phenylmenthol ≥98.0% (sum of enantiomers, HPLC) ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1CCC(C(C1)O)C(C)(C)C2=CC=CC=C2
• Isomeric SMILES: C[C@H]1CC[C@@H]([C@H](C1)O)C(C)(C)C2=CC=CC=C2

Technology Process of (1S,2R,5S)-5-Methyl-2-(2-phenylpropan-2-yl)cyclohexanol

There total 23 articles about (1S,2R,5S)-5-Methyl-2-(2-phenylpropan-2-yl)cyclohexanol 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: 92.0%

(R)-2-Isobutyl-4-oxo-5-triisopropylsilanyl-3,4-dihydro-2H-pyridine-1-carboxylic acid (1S,2R,5S)-5-methyl-2-(1-methyl-1-phenyl-ethyl)-cyclohexyl ester (126378-69-6,126378-70-9) → 2(R)-(2-methypropyl)-5-(triisopropylsilyl)-2,3-dihydro-4-pyridone (126454-97-5) + Hydroxy-acetic acid (1R,2S,5R)-5-methyl-2-(1-methyl-1-phenyl-ethyl)-cyclohexyl ester (105229-98-9) + 8-phenylmenthol (57707-91-2,65253-04-5,99528-57-1,100101-42-6,104870-75-9,104870-80-6,122517-58-2,134256-18-1)

Guidance literature:

With methanol; sodium methylate; for 16h; Heating;

DOI:10.1021/jo00296a006

Reference yield: 77.0%

[(3aS,4S,5R,6aS)-5-(tert-Butyl-dimethyl-silanyloxy)-4-(tert-butyl-dimethyl-silanyloxymethyl)-hexahydro-pentalen-(2E)-ylidene]-acetic acid (1S,2R,5S)-5-methyl-2-(1-methyl-1-phenyl-ethyl)-cyclohexyl ester (117406-89-0) → (1S,2R,5S)-8-(+)-phenylmenthol (57707-91-2) + (Z)-2-((3aS,4S,5R,6aS)-5-(((tert-butyldimethylsilyl)oxy-4-(tert-butyldimethylsilyl)oxy)methyl)hexahydropentalen-2(1H)-ylidene)ethanol (117300-46-6) + (E)-2-(((3aS,4S,5R,6aS)-5-((tert-butyldimethylsilyl)oxy-4-(tert-butyldimethylsilyl)oxy)methyl)hexahydropentalen-2(1H)-ylidene)ethanol (117300-45-5)

Guidance literature:

With diisobutylaluminium hydride; In tetrahydrofuran; at 0 ℃;

DOI:10.1016/S0040-4039(00)82039-0

Reference yield: 68.0%

C16H22O3S → (-)-8-phenylmenthol (57707-91-2,65253-04-5,99528-57-1,100101-42-6,104870-75-9,104870-80-6,122517-58-2,134256-18-1)

Guidance literature:

C₁₆H₂₂O₃S; With tris(2,2,6,6-tetramethyl-3,5-heptanedionato) manganese (III); manganese(III) triacetate dihydrate; In isopropyl alcohol; at 4 ℃; for 1h; Inert atmosphere;

With tert.-butylhydroperoxide; phenylsilane; In hexane; isopropyl alcohol; for 336h; Inert atmosphere;

DOI:10.1021/acs.orglett.6b01047

upstream raw materials:

[(3aS,4S,5R,6aS)-5-(tert-Butyl-dimethyl-silanyloxy)-4-(tert-butyl-dimethyl-silanyloxymethyl)-hexahydro-pentalen-(2E)-ylidene]-acetic acid (1S,2R,5S)-5-methyl-2-(1-methyl-1-phenyl-ethyl)-cyclohexyl ester

(2R/S,5S)-5-Methyl-2-(1-methyl-1-phenylethyl)cyclohexanone

(4aR,8aS)-4-Oxo-decahydro-naphthalene-1-carboxylic acid (1R,2S,5R)-5-methyl-2-(1-methyl-1-phenyl-ethyl)-cyclohexyl ester

bromobenzene

Downstream raw materials:

(Dimethoxy-phosphoryl)-acetic acid (1S,2R,5S)-5-methyl-2-(1-methyl-1-phenyl-ethyl)-cyclohexyl ester

(E)-9-(3-Isopropyl-2-methoxy-phenyl)-6-methyl-3-oxo-non-6-enoic acid (1S,2R,5S)-5-methyl-2-(1-methyl-1-phenyl-ethyl)-cyclohexyl ester

{1-Methyl-1-[4-methyl-2-((E)-2-methyl-buta-1,3-dienyloxy)-cyclohexyl]-ethyl}-benzene

5-Methyl-4-[5-methyl-2-(1-methyl-1-phenyl-ethyl)-cyclohexyloxy]-3a,4,7,7a-tetrahydro-isobenzofuran-1,3-dione