(S)-3-methylcyclohexanone

Base Information

• Chemical Name: (S)-3-methylcyclohexanone
• CAS No.: 24965-87-5
• Molecular Formula: C7H12 O
• Molecular Weight: 112.172
• UNII: CJE8VS4G3R
• Nikkaji Number: J441.632E
• Wikidata: Q27275491
• Mol file: 24965-87-5.mol

Synonyms:(S)-3-methylcyclohexanone;24965-87-5;(3S)-3-methylcyclohexan-1-one;3-Methylcyclohexanone, (-)-;UNII-CJE8VS4G3R;CJE8VS4G3R;(-)-3-methylcyclohexanone;Cyclohexanone, 3-methyl-, (S)-;3beta-Methylcyclohexanone;(3s)-3-methylcyclohexanone;SCHEMBL857124;(3S)-3-methyl-1-cyclohexanone;UJBOOUHRTQVGRU-LURJTMIESA-N;(-)-3-METHYL-1-CYCLOHEXANONE;(-)-(3S)-3-METHYLCYCLOHEXANONE;CYCLOHEXANONE, 3-METHYL-, (3S)-;(3S)-3-METHYLCYCLOHEXANONE, (-)-;A832176;Q27275491

Chemical Property of (S)-3-methylcyclohexanone

Chemical Property:

• Refractive Index: 1.4460
• Boiling Point: 169°Cat760mmHg
• Flash Point: 45.9°C
• PSA: 17.07000
• Density: 0.912g/cm³
• LogP: 1.76560
• XLogP3: 1.4
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 0
• Exact Mass: 112.088815002
• Heavy Atom Count: 8
• Complexity: 96.6

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1CCCC(=O)C1
• Isomeric SMILES: C[C@H]1CCCC(=O)C1

Technology Process of (S)-3-methylcyclohexanone

There total 38 articles about (S)-3-methylcyclohexanone 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: 99.0%

3-methylcyclohexen-2-one (1193-18-6) → (S)-3-methylcyclohexanone (24965-87-5)

Guidance literature:

3-methylcyclohexen-2-one; C₉H₁₉NO₂*C₅₀H₅₇O₄P; In dibutyl ether; at 60 ℃; for 0.0333333 - 0.0833333h;

With C₁₅H₂₃NO₄; In dibutyl ether; at 60 ℃; for 48h; Product distribution / selectivity;

Reference yield: 99.0%

cyclohexenone (930-68-7) + dimethyl zinc(II) (544-97-8) → (S)-3-methylcyclohexanone (24965-87-5)

Guidance literature:

dimethyl zinc(II); With copper acetylacetonate; 1-[3-((S)-1-hydroxy-2-butanylamino)-3-oxopropyl]-3-methylbenzimidazolium iodide; caesium carbonate; In tetrahydrofuran; hexane; at 20 ℃; for 0.25h;

cyclohexenone; In tetrahydrofuran; hexane; at 20 ℃; for 27h; optical yield given as %ee;

DOI:10.1021/jo300472r

Reference yield: 68.0%

(S)-5-Methyl-1-oxa-2-aza-spiro[2.5]octane (113922-31-9,121012-33-7,121029-10-5) → (S)-3-methylcyclohexanone (24965-87-5) + (5S)-2-Chloro-5-methyl-1-oxa-2-azaspiro<2.5>octane (113922-33-1,121054-66-8,121054-67-9,121054-68-0,121054-69-1)

Guidance literature:

With tert-butylhypochlorite; In diethyl ether; at 20 ℃; for 3h; Yields of byproduct given;

DOI:10.1021/ja00194a009

upstream raw materials:

3-Methylcyclohexanone

cyclohexenone

methyllithium

rac-trans-3-methylcyclohexanol

Downstream raw materials:

((S)-1-phenyl-ethyl)-oxalamic acid-((S)-3-methyl-cyclohexylidenehydrazide)

(S)-3-methyl-cyclohexanone semicarbazone

(1Ξ,4S)-2-oxo-4-methyl-cyclohexanecarboxylic acid ethyl ester

(+)-(R)-4-methyl-2-cyclohexene-1-one

Refernces

• 1、 Scharinger, Fabian,Márk Pálv?lgyi, ádám,Zeindlhofer, Veronika,Schnürch, Michael,Schr?der, Christian,Bica-Schr?der, Katharina. "Counterion Enhanced Organocatalysis: A Novel Approach for the Asymmetric Transfer Hydrogenation of Enones". . p. 3776 - 3782. Retrieved 2020/06/22.
• 2、 Wu, Wangbin,Cao, Weidi,Hu, Linfeng,Su, Zhishan,Liu, Xiaohua,Feng, Xiaoming. "Asymmetric Baeyer-Villiger oxidation: Classical and parallel kinetic resolution of 3-substituted cyclohexanones and desymmetrization of: Meso -disubstituted cycloketones". . p. 7003 - 7008. Retrieved 2019/07/31.