113405-31-5

Basic information

• Product Name: Cyclohexanone, 2,3-dimethyl-5-(1-methylethenyl)-2-(2-propenyl)-, (2S,3R,5R)-
• CAS NO: 113405-31-5
• Molecular Formula: C14H22O
• Molecular Weight: 206.328
• Mol File: 113405-31-5.mol
• Article Data: 6

Chemical Properties

• CAS DataBase Reference: Cyclohexanone, 2,3-dimethyl-5-(1-methylethenyl)-2-(2-propenyl)-, (2S,3R,5R)-(CAS DataBase Reference)
• NIST Chemistry Reference: Cyclohexanone, 2,3-dimethyl-5-(1-methylethenyl)-2-(2-propenyl)-, (2S,3R,5R)-(113405-31-5)
• EPA Substance Registry System: Cyclohexanone, 2,3-dimethyl-5-(1-methylethenyl)-2-(2-propenyl)-, (2S,3R,5R)-(113405-31-5)

Safety Data

• Hazardous Substances Data: 113405-31-5(Hazardous Substances Data)

Upstream product

• 6485-40-1 (R)-Carvone 
• 917-54-4 methyllithium 
• 106-95-6 allyl bromide 
• 15681-48-8 dimethyllithium cuprate 
• 213833-70-6 (3R,5R)-(5-isopropenyl-2,3-dimethylcyclohex-1-enyloxy)trimethylsilane 
• 24120-78-3 (1S,4R,6S)-1-methyl-4-(2-propenyl)bicyclo<4.1.0>heptan-2-one 

Downstream Products

• 214215-76-6 Acetic acid (1R,3R,4S)-3,4-dimethyl-5-oxo-4-(2-oxo-propyl)-cyclohexyl ester 
• 214215-78-8 (-)-(5R,6S)-5,6-dimethyl-6-(2-oxopropyl)cyclohex-2-enone 
• 39900-30-6 (-)-(2S,3R)-2,3-dimethyl-2-(2-oxopropyl)cyclohexanone 
• 175779-08-5 (2S,3R,5R)-5-isopropenyl-2,3-dimethyl-2-(2-oxopropyl)-cyclohexanone 

Relevant articles and documents

Bridged systems via radical cyclization reactions. Stereospecific synthesis of chiral tricyclo[6.2.1.01,5]undecanes

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Enantiospecific synthesis of (+)-(1S,2R,6S)-1,2- dimethylbicyclo[4.3.0]nonan-8-one and (-)-7-epibakkenolide-A

Synthesis of the chiral bicyclic ketone mentioned in the title starting from R-carvone, and its elaboration to 7-epibakkenolide-A is described. Conjugate addition of dimethyl copperlithium to R-carvone followed by alkylation of the intermediate enolate generated the allylated compound 6, which was transformed into the diketone 12 via a sequence of reactions comprising regiospecific Wacker oxidation, ozonation-Criegee rearrangement as key reactions. Intramolecular aldol condensation followed by catalytic hydrogenation converted the diketone 12 into the bicyclic ketone (+)-3, the optical antipode of the compound derived from the sesquiterpenes bakkenolide- A and fukinone. A 5-exo-dig radical cyclisation based strategy transformed the bicyclic ketone 3 into chiral 7-epibakkenolide-A.

Some novel electron transfer mediated cascade ring-opening reactions of bicyclo[4.1.0]ketones

The radical ring-opening reactions of cyclopropyl ketones, mediated by samarium (II) iodide and other electron transfer agents are described. This strategy allows tandem rearrangement cyclisation reactions and the trapping of the resultant samarium (III) enolates by a variety of electrophiles, for the construction of complex bicyclic systems.