13866-28-9

Usage

Uses

Used in Pharmaceutical Industry:
Cyclobutanone, 2,2-dichloro-3-phenylis used as an intermediate in the synthesis of various pharmaceuticals for its ability to contribute to the development of new drugs and medicinal compounds. Its unique structure allows for the creation of a wide range of therapeutic agents.
Used in Agrochemical Industry:
In the agrochemical sector, Cyclobutanone, 2,2-dichloro-3-phenylis utilized as an intermediate in the production of agrochemicals, playing a crucial role in the development of pesticides and other agricultural chemicals that are essential for crop protection and yield enhancement.
Used in Research and Development:
Cyclobutanone, 2,2-dichloro-3-phenylis also employed in research and development settings, where it serves as a key component in the exploration of new chemical reactions and the synthesis of novel organic compounds. Its presence in the lab accelerates the discovery of new chemical entities with potential applications in various fields.
Used in Organic Chemicals Manufacturing:
Cyclobutanone, 2,2-dichloro-3-phenylis used as a versatile building block in the manufacturing of other organic chemicals, contributing to the diversification of chemical products and the advancement of chemical synthesis techniques.

Upstream product

• 536-74-3 phenylacetylene 
• 76-02-8 trifluoroacetyl chloride 
• 100-42-5 styrene 
• 100-52-7 benzaldehyde 
• 4591-28-0 dichloroketene 
• 74-85-1 ethene 

Downstream Products

• 131388-01-7 2-methyl-4-phenylcyclopentanone 
• 52784-31-3 3-Phenylcyclobutanone 
• 136527-32-7 4,4-dichloro-3-phenylbutyric acid 
• 78920-22-6 5-hydroxy-4-phenyl-4,5-dihydro-3H-furan-2-one 
• 718599-09-8 4,4-dichloro-3-phenyl-N-propyl-butyramide 
• 708-10-1 3-phenyl-4-hydroxycyclobut-3-ene-1,2-dione 
• 1275064-79-3 dibutyl (1-hydroxy-3-phenyl-2,2-dichlorocyclobutyl)phosphonate 
• 1275064-77-1 dipropyl (1-hydroxy-3-phenyl-2,2-dichlorocyclobutyl)phosphonate 
• 1275064-73-7 dimethyl (1-hydroxy-3-phenyl-2,2-dichlorocyclobutyl)phosphonate 
• 1275064-75-9 diethyl (1-hydroxy-3-phenyl-2,2-dichlorocyclobutyl)phosphonate 
• 1274901-83-5 C₁₇H₁₆ClO₃P 
• 1274901-81-3 dipropyl (3-phenyl-2-chloro-1-cyclobutenyl) phosphate 
• 1274901-92-6 C₁₉H₂₀ClO₃P 
• 1274901-82-4 dibutyl (3-phenyl-2-chloro-1-cyclobutenyl) phosphate 

Relevant academic research and scientific papers

Stereoselective synthesis of cis-2-aryl- and 2-alkyl-1-chlorocyclopropanecarboxaldehydes

The title compounds were stereoselectively synthesized via a semi-benzilic Favorskii rearrangement of 3-aryl- and 3-alkyl-2,2-dichlorocyclobutanols, obtained by stereoselective reduction of the corresponding cyclobutanones. This synthetic pathway, starting from the synthesis of 3-substituted-2,2-dichlorocyclobutanones can be performed in one day with total yields up to 60% after purification. Reduction of the cyclobutanones yielded only cis-3-substituted cyclobutanols. Taking into account the stereoselectivity of the rearrangement, 1-halocyclopropanecarboxaldehydes, of which very few articles have been published, can be seen as highly interesting building blocks for further elaboration.

Radical C-C Bond Cleavage/Addition Cascade of Benzyl Cycloketone Oxime Ethers Enabled by Photogenerated Cyclic Iminyl Radicals

A light-driven, metal-free, and iminyl radical-mediated ring-opening C-C bond cleavage/addition cascade of O-4-methoxybenzyl oxime ethers and alkenes is described for the first time. The reaction shows a broad substrate scope and high functional group compatibility with both components, giving the corresponding valuable oxo nitriles in generally good yields. Key to the success of this protocol is the generation of cyclic iminyl radicals from the O-4-methoxybenzyl oxime ethers via a photocatalytic hydrogen atom transfer (HAT) process. The proposed main pathway is also supported by the preliminary mechanistic studies.

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.

Manganese=Catalyzed Achmatowicz Rearrangement Using Green Oxidant H2O2

Oxidation reactions have been extensively studied in the context of the transformations of biomass=derived furans. However, in contrast to the vast literature on utilizing the stoichiometric oxidants, such as m=CPBA and NBS, catalytic methods for the oxidative furan=recyclizations remain scarcely investigated. Given this, we report a means of manganese=catalyzed oxidations of furan with low loading, achieving the Achmatowicz rearrangement in the presence of hydrogen peroxide as an environmentally benign oxidant under mild conditions with wide functional group compatibility.

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.

Synthesis of Silylated Cyclobutanone and Cyclobutene Derivatives Involving 1,4-Addition of Zinc-Based Silicon Nucleophiles

A copper-catalyzed conjugate silylation of various cyclobutenone derivatives with Me2PhSiZnCl ? 2LiCl or (Me2PhSi)2Zn ? xLiCl (x≤4) to generate β-silylated cyclobutanones is reported. Trapping the intermediate enolate with ClP(O)(OPh)2 affords silylated enol phosphates that can be further engaged in Kumada cross-coupling reactions to yield silylated cyclobutene derivatives.

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.