Cyclohexanol, 5-methyl-2-(2-methyloxiranyl)-, (1R,2R,5R)-

Base Information

• Chemical Name: Cyclohexanol, 5-methyl-2-(2-methyloxiranyl)-, (1R,2R,5R)-
• CAS No.: 294634-38-1
• Molecular Formula: C10H18O2
• Molecular Weight: 170.252
• DSSTox Substance ID: DTXSID30470792
• Nikkaji Number: J185.798C
• Mol file: 294634-38-1.mol

Synonyms:Isopulegol epoxide;294634-38-1;Cyclohexanol, 5-methyl-2-(2-methyloxiranyl)-, (1R,2R,5R)-;SCHEMBL13790042;DTXSID30470792;JOEZVMKNCWMKKK-PBVVMKELSA-N

Chemical Property of Cyclohexanol, 5-methyl-2-(2-methyloxiranyl)-, (1R,2R,5R)-

Chemical Property:

• XLogP3: 1.6
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 170.130679813
• Heavy Atom Count: 12
• Complexity: 181

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1CCC(C(C1)O)C2(CO2)C
• Isomeric SMILES: C[C@@H]1CC[C@H]([C@@H](C1)O)C2(CO2)C

Technology Process of Cyclohexanol, 5-methyl-2-(2-methyloxiranyl)-, (1R,2R,5R)-

There total 2 articles about Cyclohexanol, 5-methyl-2-(2-methyloxiranyl)-, (1R,2R,5R)- 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: 88.0%

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) → (1R,2R,5R)-5-Methyl-2-(2-methyl-oxiranyl)-cyclohexanol (294634-38-1)

Guidance literature:

With 3-chloro-benzenecarboperoxoic acid; In dichloromethane; at 20 ℃; for 4h;

DOI:10.1016/S0040-4020(00)00397-5

Reference yield:

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) → (?)-trans-isopulegone (17882-43-8) + (1R,2R,5R)-5-Methyl-2-(2-methyl-oxiranyl)-cyclohexanol (294634-38-1)

Guidance literature:

With dihydrogen peroxide; In water; acetonitrile; at 90 ℃; for 4h; Reagent/catalyst; chemoselective reaction; Inert atmosphere;

DOI:10.1016/j.cattod.2014.02.027

Reference yield: 74.0%

(1R,2R,5R)-5-Methyl-2-(2-methyl-oxiranyl)-cyclohexanol (294634-38-1) → 2-<(1S,2R,4R)-2-hydroxy-4-methylcyclohexyl>-2-propen-1-ol (13834-14-5)

Guidance literature:

With lithium diisopropyl amide; In tetrahydrofuran; at 45 ℃; for 1h;

DOI:10.1016/S0040-4020(00)00397-5

upstream raw materials:

isopulegol

Downstream raw materials:

2-<(1S,2R,4R)-2-hydroxy-4-methylcyclohexyl>-2-propen-1-ol

(2S,5R)-5-Methyl-2-(2-methyl-oxiranyl)-cyclohexanone

(1R,3R,4S,8R)-9-hydroxy-p-menthol

<1R>-5(R)-methyl-2(S)-<1(S)-methyl-2-hydroxyethyl>cyclohexanol

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