83849-01-8

Basic information

• Product Name: Cyclopentanone, 2-phenyl-, oxime
• CAS NO: 83849-01-8
• Molecular Formula: C11H13NO
• Molecular Weight: 175.23
• Mol File: 83849-01-8.mol

Chemical Properties

• CAS DataBase Reference: Cyclopentanone, 2-phenyl-, oxime(CAS DataBase Reference)
• NIST Chemistry Reference: Cyclopentanone, 2-phenyl-, oxime(83849-01-8)
• EPA Substance Registry System: Cyclopentanone, 2-phenyl-, oxime(83849-01-8)

Safety Data

• Hazardous Substances Data: 83849-01-8(Hazardous Substances Data)

Upstream product

• 1198-34-1 2-Phenylcyclopentanone 
• 108-86-1 bromobenzene 
• 120-92-3 cyclopentanone 
• 825-54-7 cyclopent-1-en-1-ylbenzene 

Downstream Products

• 6604-06-4 (+/-)-trans-2-phenyl-cyclopentylamine 
• 1217438-36-2 2-phenylcyclopentanone O-acetyl oxime 
• 72887-09-3 5-methoxy-5-phenylpentanenitrile 
• 10413-05-5 5-hydroxy-5-phenylpentanenitrile 
• 2941-39-1 2-phenylhexanedinitrile 
• 40297-30-1 2-Hydroxy-2-phenylcyclopentan-1-one 
• 91132-81-9 5-oxo-5-phenyl-valeric acid amide 
• 1501-05-9 5-oxo-5-phenylvaleric acid 
• 10413-00-0 5-oxo-5-phenylpentanenitrile 
• 30154-21-3 (4E)-5-phenylpent-4-enenitrile 
• 344463-12-3 (1S,2S)-cis-propane-2-sulfonic acid [2-(4-iodo-phenyl)-cyclopentyl]-amide 

Relevant articles and documents

Copper-catalyzed ring-opening C(sp3)-N coupling of cycloketone oxime esters: Access to 1°, 2° and 3° alkyl amines

A novel copper-catalyzed C(sp3)-N coupling of cycloketone oxime esters with nitrogen nucleophiles has been realized. All of the N-aryl/alkylanilines, anilines and benzophenone imine could be employed in this protocol to produce a variety of 1°, 2° and 3° alkyl amines in one or two steps. These resultant cyano-containing alkyl amines were proven to be versatile synthetic building blocks in a variety of chemical transformations.

Enantioselective Radical Ring-Opening Cyanation of Oxime Esters by Dual Photoredox and Copper Catalysis

Catalytic enantioselective chemical reactions involving highly reactive radical species remain largely unexplored. We report herein for the first time a novel enantioselective radical ring-opening cyanation of redox-active oxime esters by dual photoreodox

Cu-Catalyzed Redox-Neutral Ring Cleavage of Cycloketone O-Acyl Oximes: Chemodivergent Access to Distal Oxygenated Nitriles

A chemodivergent copper-catalyzed ring opening of cycloketone oximes via radical-mediated C-C bond cleavage under redox-neutral conditions is described. This method allows the divergent synthesis of γ- and δ-acyloxylated, alkoxylated, and hydroxylated nitriles while avoiding the use of toxic cyanide reagents. Moreover, these reactions proceed under very mild conditions with good functional group tolerance. Notably, ring-opening reactions of the less-strained substrate cyclopentanone oxime also proceeded well under the established conditions.

Photoinduced C—C Bond Cleavage and Oxidation of Cycloketoxime Esters

A novel structural reorganization of cycloketoxime esters beyond the traditional Beckmann rearrangement process has been established to build cyano-containing ketones in the presence of photocatalyst. This novel transformation is remarkable with selective C—C bond cleavage and an oxidation process enabled by DMSO used as the solvent, oxidant, and oxygen source avoiding acid, base and toxic cyanide salts as the cyano source. Further applications in late-stage modification of complex and chiral molecules have also been reported.

Ring expansions of acyloxy nitroso compounds

Treatment of cyclopentanone and cyclobutanone-derived oximes with lead(IV) tetraacetate gives the bright blue acyloxy nitroso compounds, which upon basic hydrolysis yields the ring expansion product cyclic hydroxamic acids in 12-81% yield. Reactions of substituted cyclopentanones provide ring expanded products where the -NOH group regioselectively inserts to the more substituted position and gives a better yield compared to the treatment of the same ketone with a basic solution of Piloty's acid. Reaction of phosphines with acyloxy nitroso compounds generally generates a ring-expanded Beckmann rearrangement product that can be hydrolyzed to the corresponding lactam. Acyloxy nitroso compounds that undergo rapid hydrolysis to HNO do not show this ring expansion reactivity. These results further demonstrate the versatility of acyloxy nitroso compound to yield structurally complex materials.

Palladium-catalyzed amination of aromatic C-H bonds with oxime esters

"Chemical equation presented" We report a conceptually new approach to the direct amination of aromatic C-H bonds. In this process, an oxime ester function reacts with an aromatic C-H bond under redox-neutral conditions to form, in the case studied, an indole product. These reactions occur with relatively low catalyst loading (1 mol %) by a mechanism that appears to involve an unusual initial oxidative addition of an N-O bond to a Pd(0) species. The Pd(II) complex from oxidative addition of the N-X bond has been isolated for the first time, and evidence for the intermediacy of such oxidative addition products in the catalytic reaction has been gained.

Cyclopentyl sulfonamide derivatives

The present invention provides certain cyclopentyl sulfonamide derivatives of formula (I): useful for potentiating glutamate receptor function in a mammal. It also relates to novel cyclopentyl sulfonamide derivatives, to processes for their preparation and to pharmaceutical compositions containing them.