16750-82-6

Basic information

• Product Name: (S)-3-Methyl-6β-isopropenyl-2-cyclohexene-1-one
• Synonyms: (4S)-1,8-p-Menthadiene-3-one;(S)-3-Methyl-6β-isopropenyl-2-cyclohexene-1-one;[S,(+)]-3-Methyl-6-(1-methylethenyl)-2-cyclohexen-1-one;[S,(+)]-3-Methyl-6-(1-methylethenyl)-2-cyclohexene-1-one;[S,(+)]-3-Methyl-6β-(1-methylethenyl)-2-cyclohexene-1-one
• CAS NO: 16750-82-6
• Molecular Formula: C₁₀H₁₄O
• Molecular Weight: 150.22
• Mol File: 16750-82-6.mol
• Article Data: 11

Chemical Properties

• Boiling Point: 228.9±40.0 °C(Predicted)
• Appearance: /
• Density: 0.940±0.06 g/cm3(Predicted)
• CAS DataBase Reference: (S)-3-Methyl-6β-isopropenyl-2-cyclohexene-1-one(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-3-Methyl-6β-isopropenyl-2-cyclohexene-1-one(16750-82-6)
• EPA Substance Registry System: (S)-3-Methyl-6β-isopropenyl-2-cyclohexene-1-one(16750-82-6)

Safety Data

• Hazardous Substances Data: 16750-82-6(Hazardous Substances Data)

Usage

Uses

(S)-Isopiperitenone is a useful synthetic intermediate in the preparation of cis-isopiperitenol, which is used in the investigation of the lipase-catalyzed resolution of p-menthan-3-ol monoterpenes.

Upstream product

• 3886-78-0 (+)-2,8-p-menthadien-1-ol 
• 5989-27-5 D-limonene 
• 491-05-4 (+)-cis/trans-p-mentha-2,8-dien-1-ol 
• 22972-51-6 (1S,4R)-p-mentha-2,8-dien-1-ol 
• 491-05-4 (+)-p-menthadiene-3-ol 
• 84284-59-3 d-carene nitrosate 
• 108-24-7 acetic anhydride 
• 52154-82-2 (1R,4R)-p-mentha-2,8-dien-1-ol 

Downstream Products

• 1972-08-3 dronabinol 
• 120467-11-0 (6aR,10aR)-6,6,9-trimethyl-3-phenethyl-6a,7,8,10a-tetrahydro-6H-benzo[c]chromen-1-ol 
• 491-05-4 (+)-p-menthadiene-3-ol 
• 166990-10-9 (-)-murrayamine P 
• 166990-10-9 (+)-murrayamine-O 

Relevant articles and documents

Enantiospecific Total Syntheses of (+)-Hapalindole H and (?)-12-epi-Hapalindole U

Enantiospecific total syntheses of (+)-hapalindole H and (?)-12-epi-hapalindole U as well as the formal syntheses of (+)-hapalindole Q and (+)-12-epi-fischerindole U isothiocyanate have been described. Key steps of our approach feature expedient, highly regio- and diastereoselective Lewis acid catalyzed Friedel–Crafts reaction of indole with cyclic allylic alcohols and intramolecular reductive Heck reaction. Efficiency of the synthetic route also relies on an alkynyl aluminate complex driven regioselective nucleophilic epoxide opening from a sterically hindered site.

MnO2/TBHP: A Versatile and User-Friendly Combination of Reagents for the Oxidation of Allylic and Benzylic Methylene Functional Groups

In the presence of activated MnO2, tert-butyl hydroperoxide (TBHP) in CH2Cl2 is able to oxidize the allylic and benzylic methylene groups of different classes of compounds. I describe a one-pot oxidation protocol based on two sequential steps. In the first step, carried out at low temperature, MnO2 catalyses the oxidation of the methylene group. This is followed by a second step where reaction temperature is increased, allowing MnO2 both to catalyse the decomposition of unreacted TBHP and to oxidize allylic alcohols that could possibly be formed. The proposed oxidation procedure is generally applicable, although its efficiency, regioselectivity, and chemoselectivity are strongly dependent on the structure of the substrate. A simple and user-friendly synthetic procedure for the oxidation of allylic and benzylic methylene groups to the corresponding conjugated carbonyl derivatives is described. The proposed oxidation protocol is based on the combined use of MnO2 and tert-butyl hydroperoxide, and is generally applicable.

Daucus carota and baker's yeast mediated bio-reduction of prochiral ketones

Stereoselective reduction of prochiral ketones to the corresponding alcohols using biocatalysts has attracted much attention, from the viewpoint of green chemistry. Asymmetric reduction of indanone, tetralone and hydroxyl trimonoterpene ketones to the corresponding enantiomerically pure (S)-alcohols, using Daucus carota plant homogenate and fermented baker's yeast cells, is described. The present study illustrates the broad substrate selectivity of the dehydrogenase enzymes present in the D. carota in the synthesis of a wide range of chiral secondary alcohols of biological importance.