(1R,2R,5S)-5-Methyl-2-(1-methylethenyl)cyclohexanol

Base Information

• Chemical Name: (1R,2R,5S)-5-Methyl-2-(1-methylethenyl)cyclohexanol
• CAS No.: 122517-60-6
• Molecular Formula: C₁₀H₁₈O
• Molecular Weight: 154.252
• UNII: 6910XR09W9
• Nikkaji Number: J1.523.142D
• Wikidata: Q27138815
• ChEMBL ID: CHEMBL3120658
• Mol file: 122517-60-6.mol

Synonyms:(-)-Neoisopulegol;(-)-Neo-isopulegol;Neoisopulegol, (-)-;neo-isopulegol, rel-;6910XR09W9;UNII-6910XR09W9;CHEBI:70480;(1R,2R,5S)-5-Methyl-2-(1-methylethenyl)cyclohexanol;122517-60-6;Cyclohexanol, 5-methyl-2-(1-methylethenyl)-, (1R-(1alpha,2alpha,5beta))-;SCHEMBL8814498;CHEMBL3120658;2beta-Isopropenyl-5alpha-methylcyclohexane-1beta-ol;Q27138815;CYCLOHEXANOL, 5-METHYL-2-(1-METHYLETHENYL)-, (1R-(1.ALPHA.,2.ALPHA.,5.BETA.))-

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

Chemical Property:

• XLogP3: 3
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 1
• Exact Mass: 154.135765193
• Heavy Atom Count: 11
• Complexity: 151

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

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

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

There total 121 articles about (1R,2R,5S)-5-Methyl-2-(1-methylethenyl)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: 99.7%

(R)-Citronellal (2385-77-5) → isopulegol (7786-67-6,18674-65-2,20549-46-6,21290-09-5,29141-10-4,50373-36-9,59905-53-2,59905-54-3,96612-21-4,104870-56-6,121468-66-4,122517-60-6,122517-61-7,144541-38-8,89-79-2)

Guidance literature:

With 4,4'-methylene-bis-(2,6-diphenylphenol); acetic anhydride; at 0 ℃; for 72h; Reagent/catalyst; Time; enantioselective reaction;

Reference yield: 92.0%

(R)-Citronellal (2385-77-5) → (+)-isopulegol (104870-56-6) + isopulegol (7786-67-6,18674-65-2,20549-46-6,21290-09-5,29141-10-4,50373-36-9,59905-53-2,59905-54-3,96612-21-4,104870-56-6,121468-66-4,122517-60-6,122517-61-7,144541-38-8,89-79-2)

Guidance literature:

aluminium tris(2,6-diphenylphenoxide); In toluene; at 5 ℃; for 5h;

Reference yield: 71.0%

(R)-Citronellal (2385-77-5) → (+)-neoisopulegol (20549-46-6) + <1R-(1α,2α,5α)>-5-Methyl-2-(1-methylethenyl)cyclohexanol (144541-38-8) + <1S-(1α,2β,5β)>-5-Methyl-2-(1-methylethenyl)cyclohexanol (96612-21-4) + isopulegol (7786-67-6,18674-65-2,20549-46-6,21290-09-5,29141-10-4,50373-36-9,59905-53-2,59905-54-3,96612-21-4,104870-56-6,121468-66-4,122517-60-6,122517-61-7,144541-38-8,89-79-2)

Guidance literature:

With H-Beta-11; In cyclohexane; at 90 ℃; for 3h; under 7500.6 Torr; Further Variations:; Reagents; Product distribution;

DOI:10.1016/j.jcat.2004.03.043

upstream raw materials:

(S)-Citronellal

(S)-3,7-dimethyl-6-octen-1-ol

(1R,2R,5S)-5-methyl-2-(prop-1-en-2-yl)cyclohexyl 4-nitrobenzoate

(+)-isopulegol

Downstream raw materials:

(1R,2R,5S)-2-((S)-1-hydroxypropan-2-yl)-5-methylcyclohexanol

(1R,2R,5S)-2-((R)-1-hydroxypropan-2-yl)-5-methylcyclohexanol

(1R,2R,5S)-2-((R)-1-(tert-butyldimethylsilyloxy)propan-2-yl)-5-methylcyclohexanol

(1R,2R,5S)-2-((S)-1-(tert-butyldimethylsilyloxy)propan-2-yl)-5-methylcyclohexanol