2alpha-[(R)-alpha-Hydroxybenzyl]cyclohexanone

Base Information

• Chemical Name: 2alpha-[(R)-alpha-Hydroxybenzyl]cyclohexanone
• CAS No.: 156039-16-6
• Molecular Formula: C13H16O2
• Molecular Weight: 204.269
• DSSTox Substance ID: DTXSID40427550
• Nikkaji Number: J835.580K
• Wikidata: Q82240209
• Mol file: 156039-16-6.mol

Synonyms:AC1OET8J;156039-16-6;2alpha-[(R)-alpha-Hydroxybenzyl]cyclohexanone;SCHEMBL4754008;DTXSID40427550

Chemical Property of 2alpha-[(R)-alpha-Hydroxybenzyl]cyclohexanone

Chemical Property:

• XLogP3: 2.4
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 204.115029749
• Heavy Atom Count: 15
• Complexity: 219

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CCC(=O)C(C1)C(C2=CC=CC=C2)O
• Isomeric SMILES: C1CCC(=O)[C@@H](C1)[C@H](C2=CC=CC=C2)O

Technology Process of 2alpha-[(R)-alpha-Hydroxybenzyl]cyclohexanone

There total 53 articles about 2alpha-[(R)-alpha-Hydroxybenzyl]cyclohexanone 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: 95.0%

cyclohexanone (108-94-1,11119-77-0,9003-41-2,9075-99-4) + benzaldehyde (100-52-7) → 2‐(hydroxy(phenyl)methyl)cyclohexan‐1‐one (56072-25-4) + (2S)-2-[(R)-hydroxy(phenyl)methyl]cyclohexan-1-one (156039-16-6)

Guidance literature:

cyclohexanone; With formic acid; C₆₆H₆₃N₁₅O₆; benzoic acid; In water; at 20 ℃; for 0.5h; Inert atmosphere; Green chemistry;

benzaldehyde; In water; at 20 ℃; for 72h; Overall yield = 77 %; Overall yield = 15.7 mg; stereoselective reaction; Inert atmosphere; Green chemistry;

DOI:10.1002/adsc.201200856

Reference yield: 95.0%

trichloro<(1-cyclohexenyl)oxy>silane (17814-55-0) + benzaldehyde (100-52-7) → (2S)-2-[(R)-hydroxy(phenyl)methyl]cyclohexan-1-one (156039-16-6) + (2R,1'S)-2-(hydroxyphenylmethyl)cyclohexan-1-one (174173-19-4)

Guidance literature:

With (3S,4S)-2,5-dimethyl-3,4-diphenyl-1-piperidine-2,5,1-diazaphospholidine 1-oxide; In dichloromethane; at -78 ℃; for 8h; Product distribution; Mechanism; other phosphoramide catalysts; also in the presence of var. salts;

DOI:10.1021/ja982993v

Reference yield: 93.0%

cyclohexanone (108-94-1,11119-77-0,9003-41-2,9075-99-4) + benzaldehyde (100-52-7) → (2S)-2-[(R)-hydroxy(phenyl)methyl]cyclohexan-1-one (156039-16-6)

Guidance literature:

With benzoic acid; (1R,3S,5R)-2-azabicyclo[3.1.0]hexane-3 -carboxylic acid; In N,N-dimethyl-formamide; at -20 ℃; for 18h;

DOI:10.1016/j.tet.2015.04.075

upstream raw materials:

1-cyclohexenyloxytriethyltin

benzaldehyde

1-tri(n-butyl)stannyloxy-1-cyclohexene

1-cyclohexenyloxytrimethyltin

Downstream raw materials:

(R)-((1R,2S)-2-(benzylamino)cyclohexyl)(phenyl)methanol