99059-91-3

Usage

Uses

Used in Organic Synthesis:
3-phenylcyclobutanone oxime is used as a reagent for the conversion of carbonyl compounds to their corresponding oximes, which is an important step in the synthesis of various organic compounds.
Used in Pharmaceutical Industry:
3-phenylcyclobutanone oxime is used in the development of new drugs and pharmaceutical intermediates due to its potential biological and pharmacological properties. It is a valuable compound in the field of medicinal chemistry.
Used in Medicinal Chemistry:
3-phenylcyclobutanone oxime has been studied for its potential biological and pharmacological properties, making it a promising candidate for the development of new drugs and pharmaceutical intermediates.

Upstream product

• 13866-28-9 2,2-dichloro-3-phenylcyclobutanone 
• 100-42-5 styrene 

Downstream Products

• 96450-95-2 1-hydroxy-4-phenylpyrrolidin-2-one 
• 20132-76-7 3-phenyl-butyronitrile 
• 1401075-33-9 1-(1H-indazol-4-yl)-3-(cis-3-phenylcyclobutyl)urea 
• 318515-74-1 3-phenylcyclobutan-1-one O-benzoyl oxime 
• 90874-41-2 3-phenylcyclobutan-1-amine 

Relevant academic research and scientific papers

Copper-Catalyzed Sulfonylation of Cyclobutanone Oxime Esters with Sulfonyl Hydrazides

A copper-catalyzed radical cross-coupling of cyclobutanone oxime esters with sulfonyl hydrazides has been developed. The copper-based catalytic system proved crucial for cleavage of the C-C bond of cyclobutanone oximes and for selective C-S bond-formation involving persistent sulfonyl-metal radical intermediates. This protocol is distinguished by the low-cost catalytic system, which does not require ligand, base, or toxic cyanide salt, and by the use of readily accessible starting materials, as well as broad substrate scope, providing an efficient approach to various diversely substituted cyano-containing sulfones.

Visible-Light-Promoted Selenocyanation of Cyclobutanone Oxime Esters Using Potassium Selenocyanate

We report the visible-light-promoted selenocyanation of cyclobutanone oxime esters using potassium selenocyanate in the presence of a fac-Ir(ppy)3 catalyst for the first time. Because of the mild conditions employed and use of readily accessible potassium selenocyanate, this method is an effective and green strategy for the synthesis of cyano and selenocyano bifunctional substituted alkanes.

Nickel-Catalyzed Favorskii-Type Rearrangement of Cyclobutanone Oxime Esters to Cyclopropanecarbonitriles

A nickel-catalyzed base-promoted rearrangement of cyclobutanone oxime esters to cyclopropanecarbonitriles was developed. The ring opening of cyclobutanone oxime esters occurs at the sterically less hindered side. A base-promoted nickelacyclobutane intermediate, formed in situ, is assumed to be involved in the formation of the product.

Visible-Light Photoredox-Catalyzed Dicarbofunctionalization of Styrenes with Oxime Esters and CO2: Multicomponent Reactions toward Cyanocarboxylic Acids and γ-Keto Acids

A photoredox-catalyzed dicarbofunctionalization of styrenes with oxime esters and CO2 has been achieved. Notably, a series of four-, five-, or six-membered cyclic ketone oximes worked well to furnish a wide range of ε-, ζ-, and η-cyanocarboxylic acids in good yields. Furthermore, a series of γ-keto acids also could be obtained by employing acyclic ketone oxime esters as the carbonyl radical precursor. It provides convergent access to diverse biologically important cyanocarboxylic and γ-keto acids.

Metal-free chalcogenation of cycloketone oxime esters with dichalcogenides

We report the metal-free chalcogenation of cycloketone oxime esters with dichalcogenides via a radical process. Because of the metal-free condition and use of readily accessible dichalcogenides, this method is an effective and green strategy for the synthesis of chalcogen-substituted butyronitrile.

Metal-Free sp3 C-SCF3 Coupling Reactions between Cycloketone Oxime Esters and S-trifluoromethyl 4-Methylbenzenesulfonothioate

A novel sp3 C-SCF3 coupling reaction between cycloketone oxime esters and S-trifluoromethyl 4-methylbenzenesulfonothioate was achieved. Ethanol was found to facilitate this transformation by trapping the sulfonyl cation. The metal-free and photocatalyst-free reaction conditions, as well as the broad substrate scope, make this a green protocol for the synthesis of SCF3-substituted nitriles.

Photoinduced, Copper-Catalyzed Three-Component Annulation of gem-Dialkylthio Enynes

Photoinduced, copper-catalyzed three-component radical annulation of gem-dialkylthio enynes, cyclobutanone oxime esters, and boronic acids was achieved, forming highly functionalized aryl thienyl sulfides with both good chemo- and diastereoselectivities. The reaction proceeds through a domino sequence involving cyanoalkyl radical-mediated intramolecular annulation of gem-dialkylthio enyne, alkenyl radical-promoted C(sp3)-S bond cleavage, and sulfur-centered radical-trapped Cu(II)-facilitated C-S cross-coupling. The protocol features simultaneous establishment of cyanoalkyl, cyclopentanone, and thiophene moieties and a thioether C-S bond in one pot with broad substrate scopes and versatile functional group tolerance under mild conditions.

Synthesis of trisubstituted alkenes by Ni-catalyzed hydroalkylation of internal alkynes with cycloketone oxime esters

A method for Ni-catalyzed hydroalkylation of internal alkynes with cycloketone oxime esters was developed. The reaction has a broad substrate scope. This hydroalkylation shows excellent regio-and stereo-selectivity. This method enables readily available starting materials to be used to access a range of cyano-substituted single-configuration trisubstituted alkenes. These are valuable feedstock chemicals and are widely used in synthetic and medicinal chemistry.

Photoredox-Catalyzed Sulfonylation of O-Acyl Oximes via Iminyl Radicals with the Insertion of Sulfur Dioxide

A multicomponent sulfonylation of O-acyl oximes via iminyl radicals with the insertion of sulfur dioxide under photoredox catalysis is achieved. This multicomponent reaction of O-acyl oximes, potassium metabisulfite, alkenes, and nucleophiles under visible-light irradiation is efficient, giving rise to a range of sulfones in moderate to good yields. A broad reaction scope is presented with good functional group compatibility.

Transition-Metal-Promoted Direct C?H Cyanoalkylation and Cyanoalkoxylation of Internal Alkenes via Radical C?C Bond Cleavage of Cycloketone Oxime Esters

Transition-metal-catalyzed alkyl-Heck-type cross-coupling of olefinic C?H bonds has been a challenge in the C?H activation area. Herein, we report FeCl3-promoted efficient direct C?H cyanoalkylation of internal alkenes, that is, ketene dithioacetals, with cycloketone oxime esters via radical C?C bond cleavage under the redox-neutral conditions. With CuCl2 as the catalyst under a dioxygen atmosphere direct C?H cyanoalkoxylation of the same internal alkenes was achieved. The cyanoalkylated tetrasubstituted alkene products could be diversely transformed to cyanoalkyl-funtionalized N- and S-heterocyclic compounds. The mechanistic studies have revealed that these C?H cyanoalkylation and cyanoalkoxylation reactions proceed through a radical pathway. (Figure presented.).