3-Methyl-5-propyl-2-cyclohexen-1-one

Base Information

• Chemical Name: 3-Methyl-5-propyl-2-cyclohexen-1-one
• CAS No.: 3720-16-9
• Molecular Formula: C10H16O
• Molecular Weight: 152.236
• Hs Code.: 2914299000
• European Community (EC) Number: 223-069-0
• UNII: 6P422HTI94
• DSSTox Substance ID: DTXSID80863256
• Nikkaji Number: J205.632A
• Wikidata: Q27265263
• Metabolomics Workbench ID: 45155
• Mol file: 3720-16-9.mol

Synonyms:(S)-celery ketone;3-methyl-5-propylcyclohex-2-en-1-one

Chemical Property of 3-Methyl-5-propyl-2-cyclohexen-1-one

Chemical Property:

• Appearance/Colour: Pale yellow to colourless liquid; warm spicy woody odour, similar flavor at low levels
• Vapor Pressure: 0.0627mmHg at 25°C
• Refractive Index: 1.459
• Boiling Point: 231.339 °C at 760 mmHg
• Flash Point: 94.621 °C
• PSA: 17.07000
• Density: 0.904 g/cm³
• LogP: 2.71190
• XLogP3: 2.3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 2
• Exact Mass: 152.120115130
• Heavy Atom Count: 11
• Complexity: 179

Purity/Quality:

99% ^*data from raw suppliers

3-Methyl-5-propylcyclohex-2-enone ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCCC1CC(=CC(=O)C1)C
• Description: 3-Methyl-5-propyl-2-cyclohexen-l-one has a warm, spicy, woody odor with a similar flavor at low levels. May be prepared by condensation of butyric aldehyde with ethyl acetoacetate in the presence of diethylamine and subsequent saponification with a 10% KOH solution; or by condensation in the presence of piperidine in ethanol solution.

Technology Process of 3-Methyl-5-propyl-2-cyclohexen-1-one

There total 16 articles about 3-Methyl-5-propyl-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: 88.0%

triisopropyl-(5-methyl-3-propyl-hex-5-en-1-ynyloxy)-silane (765906-69-2) → 3-methyl-5-propyl-2-cyclohexen-1-one (3720-16-9)

Guidance literature:

With bis(trifluoromethanesulfonyl)amide; In dichloromethane; at 20 ℃; for 1h;

DOI:10.1016/j.tet.2006.06.037

Reference yield: 88.0%

4-propyl-6-triisopropylsilanyloxy-2-trimethylsilanylmethyl-hex-1-en-5-yne (765906-73-8) → 3-methyl-5-propyl-2-cyclohexen-1-one (3720-16-9)

Guidance literature:

With bis(trifluoromethanesulfonyl)amide; In dichloromethane; at 20 ℃; for 2h;

DOI:10.1021/ja046586x

Reference yield: 84.0%

diethyl 1,2,6-trimethyl-4-propyl-1,4-dihydropyridine-3,5-dicarboxylate → 3-methyl-5-propyl-2-cyclohexen-1-one (3720-16-9)

Guidance literature:

With hydrogenchloride; In ethanol; for 30h; Heating;

DOI:10.1007/s10593-007-0006-0

upstream raw materials:

ethyl acetoacetate

butyraldehyde

diethyl acetylmalonate

3-Methylbutenoic acid

Downstream raw materials:

3-Methyl-5-propyl-phenol

3-methyl-5-propylcyclohexanone

methyl E-3-methyl-5-propylcyclohexylidene acetate

methyl Z-3-methyl-5-propylcyclohexylidene acetate

Refernces

• 1、 Wang, Li,Gong, Qing-Ping,Liu, Xiao-Jun,Li, Yong-Hong,Huang, Ping,Wang, Bi-Qin,Zhao, Ke-Qing. "Organocatalyst-mediated aldolrobinson cascade reactions: A convenient synthesis of substituted cyclohex-2-enones". supporting information; experimental part. p. 138 - 139. Retrieved 2011/04/15.
• 2、 Stupnikova,Petushkova,Muceniece,Lūsis. "Recyclization of 1,4-dihydropyridine derivatives in acidic medium". . p. 41 - 49. Retrieved 2007/10/03.