52784-31-3

Usage

Uses

Used in Pharmaceutical Development:
3-Phenyl-cyclobutan-1-one is utilized as a key intermediate in the synthesis of pharmaceutical compounds, leveraging its bioactive properties for the development of new drugs.
Used in Organic Synthesis:
In the field of organic synthesis, 3-Phenyl-cyclobutan-1-one serves as a versatile intermediate, contributing to the production of a variety of chemical products including fragrances, flavors, and polymers due to its unique reactivity and structure.
Used in Fragrance and Flavor Industry:
3-Phenyl-cyclobutan-1-one is employed as a building block in creating complex aromatic compounds, enhancing the scent and taste profiles in the fragrance and flavor industry.
Used in Polymer Production:
3-PHENYL-CYCLOBUTAN-1-ONE is also used as a component in polymer chemistry, contributing to the development of new polymeric materials with specific properties tailored for various applications.

InChI:InChI=1/C10H10O/c11-10-6-9(7-10)8-4-2-1-3-5-8/h1-5,9H,6-7H2

Upstream product

• 186581-53-3 diazomethane 
• 103-82-2 phenylacetic acid 
• 100-42-5 styrene 
• 127-19-5 N,N-dimethyl acetamide 
• 91391-31-0 2-chloro-3-phenylcyclobut-2-enone 
• 38425-47-7 3-phenyl-2-cyclobuten-1-one 
• 340-01-2 4,4-dichloro-3,3-difluoro-1-phenyl-cyclobutene 
• 536-74-3 phenylacetylene 
• 1959-45-1 3,3-difluoro-1-phenylcyclobutene 
• 76-02-8 trifluoroacetyl chloride 
• 14752-66-0 sodium p-chlorobenzenesulphinate 
• 873-55-2 sodium benzenesulfonate 
• 824-79-3 sodium 4-methylbenzenesulfinate 
• 150639-15-9 (1s,3s)-3-phenylcyclobutanol 

Downstream Products

• 100340-33-8 3-phenyl-1-vinylcyclobutanol 
• 64145-51-3 3-phenylcyclopentanone 
• 2722-36-3 3-phenyl-1-butanol 
• 1008-73-7 4-phenyldihydrofuran-2(3H)-one 
• 1008-73-7 (R)-4-phenyl-4,5-dihydrofuran-2(3H)-one 
• 68844-05-3 4-phenyldihydrofuran-2-one 
• 1896-62-4 (E)-benzalacetone 
• 1533-20-6 1,3-diphenylbutane-1-one 
• 1008-76-0 4,5-dihydro-5-phenyl-2(3H)-furanone 
• 1008-73-7 (+)-3-phenyl-γ-lactone 

Relevant academic research and scientific papers

Synthesis of 1-Pyrroline by Denitrogenative Ring Expansion of Cyclobutyl Azides under Thermal Conditions

We herein report an efficient and systematic synthesis of 1-pyrrolines from cyclobutyl azides under thermal and neutral conditions. The reaction proceeded without any additional reagents, and nitrogen was generated as the sole by-product. Furthermore, the generated 1-pyrrolines could be continuously transformed into pyrroles, N-Boc-amines, and oxaziridines in an one-pot manner. (Figure presented.).

Desymmetrization of Prochiral Cyclobutanones via Nitrogen Insertion: A Concise Route to Chiral γ-Lactams

Asymmetric access to γ-lactams is achieved via a cyclobutanone ring expansion using widely available (1S,2R)-1-amino-2-indanol for chiral induction. Mechanistic analysis of the key N,O-ketal rearrangement reveals a Curtin–Hammett scenario, which enables a downstream stereoinduction (up to 88:12 dr) and is corroborated by spectroscopic, crystallographic, and computational studies. In combination with an easy deprotection protocol, this operationally simple sequence allows the synthesis of a range of optically pure γ-lactams, including those bearing all-carbon quaternary stereocenters. In addition, the formal synthesis of drug molecules baclofen, brivaracetam, and pregabalin further demonstrates the synthetic utility and highlights the general applicability of the presented method.

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.

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.