3-Methyl-2-cyclohexen-1-one

Base Information

• Chemical Name: 3-Methyl-2-cyclohexen-1-one
• CAS No.: 1193-18-6
• Molecular Formula: C7H10O
• Molecular Weight: 110.156
• Hs Code.: 29142990
• European Community (EC) Number: 214-769-7
• NSC Number: 43632
• UNII: 786Y352V9X
• DSSTox Substance ID: DTXSID8035186
• Nikkaji Number: J109.957D
• Wikidata: Q27160291
• Metabolomics Workbench ID: 44938
• ChEMBL ID: CHEMBL3139347
• Mol file: 1193-18-6.mol

Synonyms:3-methyl-2-cyclohexen-1-one;3-methylcyclohex-2-en-1-one;MCH cpd

Chemical Property of 3-Methyl-2-cyclohexen-1-one

Chemical Property:

• Appearance/Colour: Clear very slightly yellow to brown liquid
• Vapor Pressure: 0.315mmHg at 25°C
• Melting Point: -21°C
• Refractive Index: n20/D 1.494(lit.)
• Boiling Point: 201 °C at 760 mmHg
• Flash Point: 68.3 °C
• PSA: 17.07000
• Density: 0.964 g/cm³
• LogP: 1.68570
• Storage Temp.: 2-8°C
• Water Solubility.: insoluble
• XLogP3: 0.8
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 0
• Exact Mass: 110.073164938
• Heavy Atom Count: 8
• Complexity: 133

Purity/Quality:

98%, ^*data from raw suppliers

Seudenone ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 22-36-20/21/22
• Safety Statements: 36/37/39-26-24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=CC(=O)CCC1
• Description: May be prepared by acid hydrolysis and decarboxylation of the corresponding 4-carbetoxy derivative; by oxidation of 1-methylcyclohex-l-ene with chromium trioxide in acetic acid; by cyclization of 3-carbetoxy-6-chlorohept-5-en-2-one with sulfuric acid.
• Uses: 3-Methyl-2-cyclohexen-1-one was used in the synthesis of 19-nor-1α, 25-dihydroxyvitamin D(3) derivatives. It was also used in sex pheromone of the Douglas-fir beetle. Used in nut flavor. 3-Methyl-2-cyclohexenone is an insect sex pheromone of the Douglas-fir beetle. It can be used as a starting material:In the total synthesis of (?)-ar-tenuifolene, a naturally occurring aromatic sesquiterpene.To synthesize an organic building block 2-trimethylsilyl-3-methyl-cyclohexenone.In the total synthesis of natural diterpenoids (+)-taiwaniaquinone H and (+)-dichroanone.

Technology Process of 3-Methyl-2-cyclohexen-1-one

There total 186 articles about 3-Methyl-2-cyclohexen-1-one 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-methylcyclohex-2-en-1-ol (21378-21-2,54423-21-1) → 3-methylcyclohexen-2-one (1193-18-6)

Guidance literature:

With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; potassium tert-butylate; copper(I) triflate; 5-[(2S)-pyrrolidine-2-yl]-1H-tetrazole; In N,N-dimethyl-formamide; at 25 ℃; for 0.5h; Catalytic behavior;

DOI:10.1016/j.tet.2014.11.015

Reference yield: 97.0%

1-methoxy-3-methyl-benzene (100-84-5) → 3-methylcyclohexen-2-one (1193-18-6) + 3-Methylcyclohexanone (591-24-2,625-96-7)

Guidance literature:

With N,N,N,N,N,N-hexamethylphosphoric triamide; lithium; In tetrahydrofuran; ethanol; at -30 ℃; for 2h;

Reference yield: 89.0%

1-methylcyclohex-1-ene (591-49-1) → 3-methylcyclohexen-2-one (1193-18-6)

Guidance literature:

With tert.-butylhydroperoxide; Rh₂(Cap)4; potassium carbonate; In dichloromethane; for 0.333333h;

DOI:10.1021/ja045330o

upstream raw materials:

2,6-dimethylpyridine

tert.-butylhydroperoxide

1-methylcyclohex-1-ene

formic acid

Downstream raw materials:

2-methoxy-3-methyl-cyclohex-2-enone

1-<(triethylsilyl)oxy>-3-methylcyclohex-1-ene

(1-methyl-3-oxo-cyclohexyl)-thiophosphonic acid O,O'-diethyl ester

(1-methyl-3-oxo-cyclohexyl)-phosphonic acid dimethyl ester