509324-10-1

Basic information

• Product Name: (R)-2-methyl-2-(4-methylphenyl)cyclopentanone
• Synonyms: (R)-2-methyl-2-(4-methylphenyl)cyclopentanone
• CAS NO: 509324-10-1
• Molecular Weight: 188.269
• Mol File: 509324-10-1.mol

Chemical Properties

• CAS DataBase Reference: (R)-2-methyl-2-(4-methylphenyl)cyclopentanone(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-2-methyl-2-(4-methylphenyl)cyclopentanone(509324-10-1)
• EPA Substance Registry System: (R)-2-methyl-2-(4-methylphenyl)cyclopentanone(509324-10-1)

Safety Data

• Hazardous Substances Data: 509324-10-1(Hazardous Substances Data)

Upstream product

• 1071119-43-1 (S)-9-Methyl-9-p-tolyl-1,4-dioxa-spiro[4.4]nonan-6-one 
• 174229-35-7 3-methyl-3-(4-methylphenyl)-4-oxopentanal 
• 94853-56-2 3-methyl-3-(4-methylphenyl)-pent-4-enal 
• 130633-06-6 (E)-3-(4-methylphenyl)-but-2-en-1-ol 
• 76430-23-4 2-methylcyclopentanone dimethyl acetal 
• 1120-72-5 2-Methylcyclopentanone 
• 624-31-7 4-tolyl iodide 
• 509323-88-0 1-methyl-2-(S)-(2-methyl-cyclopent-1-enyloxymethyl)-pyrrolidine 
• 612036-15-4 5-methyl-5-(4-methylphenyl)-cyclopent-2-en-1-one 

Downstream Products

• 111621-35-3 (+/-)-Tochuinyl acetate 
• 51941-57-2 (1R^*,2S^*)-1,2-Dimethyl-2-(4-methylphenyl)cyclopentanemethanol 

Relevant articles and documents

High stereoselectivity in chelation-controlled intermolecular Heck reactions with aryl chlorides, vinyl chlorides and vinyl triflates

Highly stereoselective chelation-controlled Pd(0)-catalyzed β-arylations and β-vinylations of a five-membered chiral, pyrrolidine-based vinyl ether were achieved using aryl- and vinyl chlorides as substrates, yielding quaternary 2-aryl/vinyl-2-methyl cyclopentanones in 89-96% ee under neutral reaction conditions. This journal is The Royal Society of Chemistry.

Enantiopure 2-aryl-2-methyl cyclopentanones by an asymmetric chelation-controlled Heck reaction using aryl bromides: increased preparative scope and effect of ring size on reactivity and selectivity

Quaternary 2-aryl-2-methyl cyclopentanones were obtained in 85-94% ee via Pd(0)-catalyzed chelation-controlled asymmetric arylation of a cyclopentenyl ether with aryl bromides and subsequent hydrolysis. Two new cyclohexenyl ethers were synthesized and evaluated as Heck substrates with both aryl iodides and bromides under different reaction conditions. Arylations of the six-membered vinyl ether 1-methyl-2-(S)-(cyclohex-1-enyloxymethyl)-pyrrolidine with aryl bromides were achieved with t-Bu3P-promoted palladium catalysis using either classical or microwave heating. Isolated Heck products were also obtained in high diastereoselectivities (94-98% de).

Enantioselective synthesis of 2-alkyl-2-aryl cyclopentanones by asymmetric epoxidation of tetrasubstituted cyclobutylidene olefins and epoxide rearrangement

This letter describes a highly enantioselective epoxidation of tetrasubstituted benzylidenecyclobutanes using glucose-derived ketone as catalyst and oxone as oxidant. The Et2AlCl promoted rearrangement of the resulting epoxides provides 2-alkyl

A new highly asymmetric chelation-controlled heck arylation

This communication describes the development of a new highly asymmetric chelation-controlled Heck arylation. The methodology permits formation of 2-aryl-2-methyl cyclopentanones in good to very good two-step yields (45-78%) with excellent chiral enrichmen

Stereoselective total synthesis of (±)-Tochuinyl acetate and (±)-dihydrotochuinyl acetates

Details of the first total synthesis of the marine natural product dihydrotochuinyl acetate is described. Cyclopentenone annulation of p-methylacetophenone via a Claisen rearrangement- Wacker oxidation based sequence generated the cyclopentenone 3, a know

Stereochemical Evidence for a Carbonium Ion Rearrangement during Reaction of Dimethyltitanium Dichloride with a Ketone

Racemization during the reaction of dimethyltitanium dichloride with the 2,2-disubstituted cyclopentanone (-)-3 of high enantiomeric purity provides stereochemical evidence for a carbonium ion rearrangement during this dimethylation process.