254892-91-6

Usage

Uses

Used in Pharmaceutical Industry:
3-(4-bromophenyl)cyclobutanone is used as a key intermediate in the synthesis of selective T-type calcium channel blockers. These blockers play a crucial role in the treatment of various cardiovascular and neurological disorders by modulating the flow of calcium ions through T-type calcium channels, which are essential for the proper functioning of the heart and nervous system.

Upstream product

• 2039-82-9 1-bromo-4-ethenyl-benzene 
• 107-06-2 1,2-dichloro-ethane 
• 1122-91-4 4-bromo-benzaldehyde 
• 463-51-4 Ketene 
• 127-19-5 N,N-dimethyl acetamide 
• 254892-87-0 3-(4-bromophenyl)-2,2-dichlorocyclobutan-1-one 

Downstream Products

• 1019842-34-2 1-(1-benzyloxy-propa-1,2-dienyl)-3-(4-bromo-phenyl)-cyclobutanol 
• 1183047-51-9 3-(4-bromophenyl)cyclobutanol 
• 1236357-60-0 1-bromo-4-(3,3-difluorocyclobutyl)benzene 
• 916814-02-3 cis-3-(4-bromophenyl)cyclobutanol 

Relevant academic research and scientific papers

PROCESSES FOR PREPARING TRIAZOLE GLYCOLATE OXIDASE INHIBITORS

The present disclosure provides processes for preparing 1,2,3-triazole-4-carboxylic acid related compounds of formulae (I) and (II) via a Suzuki coupling reaction. The Suzuki coupling reaction is achieved by coupling a compound of formula (IV), a boron-containing derivative of 1,2,3-triazole-4-carboxylate, with a cycloalkyl phenyl halide or sulfonate of formula (V).

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.

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.

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.

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.

COMPOUNDS USEFUL IN MODULATING THE FARNESOID X RECEPTOR AND METHODS OF MAKING AND USING THE SAME

Provided are compounds that can act as a modulator of a farnesoid X receptor (FXR) and that can be useful in the treatment of diseases and/or disorders associated with the FXR. Compositions including such compounds are also provided along with methods for preparing compounds of the present invention and their use.

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.

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.