[(1R,2S,5R)-5-methyl-2-(propan-2-yl)cyclohexyl]methanol

Base Information

• Chemical Name: [(1R,2S,5R)-5-methyl-2-(propan-2-yl)cyclohexyl]methanol
• CAS No.: 27373-94-0
• Molecular Formula: C₁₁H₂₂O
• Molecular Weight: 170.295
• European Community (EC) Number: 823-213-8
• Nikkaji Number: J2.198.716F
• Mol file: 27373-94-0.mol

Synonyms:27373-94-0;[(1R,2S,5R)-5-methyl-2-(propan-2-yl)cyclohexyl]methanol;((1R,2S,5R)-2-Isopropyl-5-methylcyclohexyl)methanol;[(1R,2S,5R)-5-methyl-2-propan-2-ylcyclohexyl]methanol;SCHEMBL7747412;G68481;EN300-1718798

Chemical Property of [(1R,2S,5R)-5-methyl-2-(propan-2-yl)cyclohexyl]methanol

Chemical Property:

• XLogP3: 3.4
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 2
• Exact Mass: 170.167065321
• Heavy Atom Count: 12
• Complexity: 131

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

Technology Process of [(1R,2S,5R)-5-methyl-2-(propan-2-yl)cyclohexyl]methanol

There total 3 articles about [(1R,2S,5R)-5-methyl-2-(propan-2-yl)cyclohexyl]methanol 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: 90.0%

2-(((1R,2S,5R)-2-isopropyl-5-methylcyclohexyl)methyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane → (1R,2S,5R)-1-(hydroxymethyl)-2-isopropyl-5-methylcyclohexane (27373-94-0)

Guidance literature:

2-(((1R,2S,5R)-2-isopropyl-5-methylcyclohexyl)methyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane; With sodium perborate tetrahydrate; water; In tetrahydrofuran; at 40 ℃; for 0.0166667h; Schlenk technique; Flow reactor;

With sodium thiosulfate; In tetrahydrofuran; Schlenk technique; Flow reactor;

DOI:10.1021/acs.orglett.1c01222

Reference yield:

(2R,5S)-menthone (10458-14-7,14073-97-3,17627-49-5,7786-64-3) → (1R,2S,5R)-1-(hydroxymethyl)-2-isopropyl-5-methylcyclohexane (27373-94-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 87 percent / n-BuLi / tetrahydrofuran; hexane / 1.) 2 h, 65 deg C; 2.) 16 h, r.t.

2: 1.) BH₃*Me₂S; 2.) NaOH, H₂O₂ / 1.) hexane

With sodium hydroxide; n-butyllithium; dimethylsulfide borane complex; dihydrogen peroxide; In tetrahydrofuran; hexane;

DOI:10.1016/S0040-4020(01)80834-6

Reference yield:

Phthalic acid mono-((2S,5R)-2-isopropyl-5-methyl-cyclohexylmethyl) ester → (1R,2S,5R)-1-(hydroxymethyl)-2-isopropyl-5-methylcyclohexane (27373-94-0) + (1S,2S,5R)-2-isopropyl-5-methyl-1-(hydroxymethyl)cyclohexane (31481-55-7)

Guidance literature:

With sodium hydroxide; In water; for 2h; Yield given. Yields of byproduct given. Title compound not separated from byproducts; Heating;

upstream raw materials:

(2R,5S)-menthone

Refernces

• 1、 Bernardi, Anna,Comotti, Angiolina,Gennari, Cesare,Hewkin, Cheryl T.,Goodman, Jonathan M.,et al.. "Computer-Assisted Design of Chiral Boron Enolates: The Role of Ate Complexes in Determining Aldol Stereoselectivity.". . p. 1227 - 1242. Retrieved 2007/10/02.
• 2、 Falorni, Massimo,Lardicci, Luciano,Uccello-Barretta, Gloria,Giacomelli, Giampaolo. "ALKYLMETAL ASYMMETRIC REDUCTION. XIX. GRIGNARD REAGENTS DERIVED FROM NATURALLY OCCURRING PRODUCTS AS REDUCING AGENTS OF KETONES". . p. 495 - 500. Retrieved 2007/10/02.