4573-50-6

Basic information

• Product Name: (R)-6-(isopropyl)-3-methylcyclohex-2-en-1-one
• Synonyms: (R)-6-(isopropyl)-3-methylcyclohex-2-en-1-one;L-PIPERITONE;L-PIPERITONE, NATURAL;L-PIPERITONE, SYNTHETIC;(R)-(-)-Piperitone;(R)-6-Isopropyl-3-methyl-2-cyclohexen-1-one;2-Cyclohexen-1-one, 3-methyl-6-(1-methylethyl)-, (6R)-;Einecs 224-957-0
• CAS NO: 4573-50-6
• Molecular Formula: C₁₀H₁₆O
• Molecular Weight: 152.23344
• EINECS: 224-957-0
• Mol File: 4573-50-6.mol
• Article Data: 8

Chemical Properties

• Boiling Point: 233°C at 760 mmHg
• Flash Point: 90.9°C
• Appearance: /
• Density: 0.915g/cm³
• Vapor Pressure: 0.0572mmHg at 25°C
• Refractive Index: 1.464
• Water Solubility: 2.479g/L at 20℃
• CAS DataBase Reference: (R)-6-(isopropyl)-3-methylcyclohex-2-en-1-one(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-6-(isopropyl)-3-methylcyclohex-2-en-1-one(4573-50-6)
• EPA Substance Registry System: (R)-6-(isopropyl)-3-methylcyclohex-2-en-1-one(4573-50-6)

Safety Data

• Hazardous Substances Data: 4573-50-6(Hazardous Substances Data)

Usage

Chemical Properties

Light yellowish liquid; herbaceous minty aroma.

Aroma threshold values

High strength odor, recommend smelling in a 1% solution or less.

Flammability and Explosibility

Notclassified

InChI:InChI=1/C10H16O/c1-7(2)9-5-4-8(3)6-10(9)11/h6-7,9H,4-5H2,1-3H3/t9-/m1/s1

Upstream product

• 1415503-66-0 2-isopropyl-5-methylcyclohexa-1,5-dien-1-yl 2-chloroacetate 
• 491-05-4 (+)-p-menthadiene-3-ol 
• 10458-14-7 (2R,5S)-menthone 
• 142835-88-9 (2S,5R)-6-phenylselenenylmenthone 
• 74185-00-5 (3R,6S)-3-methyl-6-(prop-2-yl)-1-trimethylsilyloxy-cyclohexene 
• 491-09-8 3-terpinolenone 

Downstream Products

• 23283-97-8 (+)-(1S,2R,5R)-isomenthol 
• 1196-31-2 (1R,4R)-(+)-isomenthone 
• 65733-27-9 cis-piperitol 
• 65733-28-0 (+)-trans-piperitol 
• 15840-87-6 3,3'-Dimethyl-6,6'-bis(1-methylethyl)-3,3'-bicyclohexanon 
• 105252-30-0 6,6'-Dimethyl-3,3'-bis(1-methylethyl)-8,8'-spirobioctan>-2,2'-dion 
• 105367-50-8 (3S,6R)-3-Isopropyl-6-methyl-8-methylene-bicyclo[4.2.0]octan-2-one 
• 105367-51-9 (3S,6S)-3-Isopropyl-6-methyl-8-methylene-bicyclo[4.2.0]octan-2-one 
• 142835-89-0 3,3-Dimethyl-6-(1-methylethyl)-1-cyclohexanon 
• 2216-51-5 (-)-menthol 
• 2216-52-6 Neomenthol 
• 491-04-3 (1R*,6S*)-6-isopropyl-3-methylcyclohex-2-en-1-ol 
• 491-04-3 trans-6-isopropyl-3-methylcyclohex-2-en-1-ol 
• 105252-19-5 trans-2-Acetyl-3,3-dimethyl-6-(1-methylethyl)-1-cyclohexanon 

Relevant articles and documents

Synthesis of Cyclic Enones by Allyl-Palladium-Catalyzed α,β-Dehydrogenation

The use of allyl-palladium catalysis for the one-step α,β-dehydrogenation of ketones via their zinc enolates is reported. The optimized protocol utilizes commercially available Zn(TMP)2 as base and diethyl allyl phosphate as oxidant. Notably, this transformation operates under salt-free conditions and tolerates a diverse scope of cycloalkanones.

Hydrolytic enantioselective protonation of cyclic dienyl esters and a β-diketone with chiral phase-transfer catalysts

Hydrolytic enantioselective protonation of dienyl esters and a β-diketone catalyzed by phase-transfer catalysts are described. The latter reaction is the first example of an enantio-convergent retro-Claisen condensation. Corresponding various optically active α,β-unsaturated ketones having tertiary chiral centers adjacent to carbonyl groups were obtained in good to excellent yields and enantiomeric ratios (83-99%, up to 97.5:2.5 er).

The Lewis acid-catalyzed intramolecular asymmetric ene reaction using a chiral α-cyanovinylic sulfoxide as an enophile

A chiral α-cyanovinylic sulfoxide served as an efficient chiral enophile in a Lewis acid-catalyzed intramolecular ene reaction. Use of diethylaluminum chloride as a catalyst provided extremely high stereoselectivity in the ene reaction. The stereochemistry of the ene reaction products were determined by chemical correlation and the NMR spectral analysis. A mechanistic pathway for the asymmetric induction is presented on the basis of the stereochemical results obtained.