885267-15-2

Usage

Uses

Used in Pharmaceutical Research:
3-(3-Bromophenyl)cyclobutanone is used as a building block for the synthesis of various pharmaceutical compounds due to its unique structure and potential biological activities.
Used in Organic Synthesis:
3-(3-Bromophenyl)cyclobutanone is used as a key intermediate in the synthesis of complex organic molecules, contributing to the development of new chemical entities with potential applications in various fields.
Used in Material Science:
3-(3-Bromophenyl)cyclobutanone may have applications in material science, potentially contributing to the development of new materials with unique properties.
Used as a Precursor for Synthesis:
3-(3-Bromophenyl)cyclobutanone serves as a precursor for the synthesis of other valuable chemical compounds, expanding its utility in the chemical industry.
Used in Anticancer Research:
3-(3-Bromophenyl)cyclobutanone is studied for its potential as an anti-cancer agent, with ongoing research exploring its biological activities and potential therapeutic applications in cancer treatment.

InChI:InChI=1/C10H9BrO/c11-9-3-1-2-7(4-9)8-5-10(12)6-8/h1-4,8H,5-6H2

Upstream product

• 2039-86-3 3-bromostyrene 
• 140-89-6 potassium ethyl xanthogenate 
• 76-02-8 trifluoroacetyl chloride 
• 108-75-8 2,4,6-trimethyl-pyridine 
• 127-19-5 N,N-dimethyl acetamide 
• 463-51-4 Ketene 

Downstream Products

• 931430-34-1 [3-(3-Bromo-phenyl)-cyclobutylidene]-acetic acid ethyl ester 
• 1376692-37-3 4-(3-bromophenyl)dihydrofuran-2(3H)-one 
• 1418274-34-6 3-(3-Bromophenyl)-1-(2-chloro-4-((5-cyclopropyl-3-(2,6-dichlorophenyl)isoxazol-4-yl)methoxy)phenyl)cyclobutanol 
• 1418274-09-5 C₃₀H₂₄Cl₃NO₅ 
• 1418274-35-7 3-(3-Cyanophenyl)-1-(2-chloro-4-((5-cyclopropyl-3-(2,6-dichlorophenyl)isoxazol-4-yl)methoxy)phenyl)cyclobutanol 
• 1418274-11-9 C₃₁H₂₇Cl₃N₂O₆S 
• 1418274-37-9 3-(3-(Benzylthio)phenyl)-1-(2-chloro-4-((5-cyclopropyl-3-(2,6-dichlorophenyl)isoxazol-4-yl)methoxy)phenyl)cyclobutanol 
• 1418274-13-1 1-(2-chloro-4-((5-cyclopropyl-3-(2,6-dichlorophenyl)isoxazol-4-yl)methoxy)phenyl)-3-(3-(methylsulfonyl)phenyl)cyclobutanol 
• 1418274-47-1 3-((1s,3s)-3-(2-chloro-4-((5-cyclopropyl-3-(2,6-dichlorophenyl)isoxazol-4-yl)methoxy)phenyl)-3-hydroxycyclobutyl)benzoic acid 
• 1418274-49-3 3-((1s,3s)-3-(2-chloro-4-((5-cyclopropyl-3-(2.6-dichlorophenyl)isoxazol-4-yl)methoxy)phenyl)-3-hydroxycyclobutyl)-N-(methylsulfonyl)benzamide 
• 1431299-16-9 (R)-4-(3-bromophenyl)dihydrofuran-2(3H)-one 
• 1418274-12-0 3-(3-(2-chloro-4-((5-cyclopropyl-3-(2,6-dichlorophenyl)isoxazol-4-yl)methoxy)phenyl)-3-hydroxycyclobutyl)benzenesulfonamide 
• 1418274-38-0 3-(3-(2-chloro-4-((5-cyclopropyl-3-(2,6-dichlorophenyl)isoxazol-4-yl)methoxy)phenyl)-3-hydroxycyclobutyl)benzene-1-sulfonyl chloride 
• 1065168-46-8 [3-(3-Bromo-phenyl)-cyclobutylidene]-acetic acid methyl ester 

Relevant academic research and scientific papers

Directing-Group-Based Strategy Enabling Intermolecular Heck-Type Reaction of Cycloketone Oxime Esters and Unactivated Alkenes

A new type of coupling between unactivated olefins and nonstabilized alkyl radicals was achieved, which enabled the first intermolecular Heck-type reaction of cycloketone oxime esters and unactivated alkenes. This directing-group-based strategy was compatible with various unactivated alkenes and cyclobutanone-, cyclopentanone-, and cyclohexanone-derived oxime esters. Density functional theory calculations showed that both excellent regioselectivities and good diastereoselectivities could be ascribed to the 2-butanol-assisted concerted H-OBz elimination of the conformationally strained metallacyclic transition state.

Novel substituted isoxazole FXR agonists with cyclopropyl, hydroxycyclobutyl and hydroxyazetidinyl linkers: Understanding and improving key determinants of pharmacological properties

Several isoxazole-containing series of FXR agonists have been published over the last 15 years, subsequent to the prototypical amphiphilic ‘hammerhead’-type structure that was originally laid out by GW4064, the first potent synthetic FXR agonist. A set of novel compounds where the hammerhead is connected to the terminal carboxylic acid-bearing aryl or heteroaryl moiety by either a cyclopropyl, a hydroxycyclobutyl or a hydroxyazetidinyl linker was synthesized in order to improve upon the ADME properties of such isoxazoles. The resulting compounds all demonstrated high potencies at the target receptor FXR but with considerable differences in their physicochemical and in vivo profiles. The structure–activity relationships for key chemical features that have a major impact on the in vivo pharmacology of this series are discussed.

Baeyer–Villiger monooxygenase-catalyzed desymmetrizations of cyclobutanones. Application to the synthesis of valuable spirolactones

A series of γ-butyrolactone derivatives, including some spiranic ones, was obtained through desymmetrization of the corresponding prochiral 3-substituted cyclobutanones via Baeyer–Villiger monooxygenase (BVMO)-catalyzed oxidation. After reaction optimization using several commercial enzymes, both antipodes of various lactones were synthesized in most cases with >90% conversion and >80% enantiomeric excess under mild reaction conditions. In some cases alcohol formation was also observed (up to 40% conversion) as an undesired side reaction due to the presence of alcohol dehydrogenases in these preparations. Selected transformations were achieved on a 100 mg scale showing the possibilities of these oxidative biocatalysts as a new source of highly interesting compounds.

Lactonization reactions through hydrolase-catalyzed peracid formation. Use of lipases for chemoenzymatic Baeyer-Villiger oxidations of cyclobutanones

A one-pot chemoenzymatic method has been described for the synthesis of γ-butyrolactones starting from the corresponding ketones through a Baeyer-Villiger reaction. The approach is based on a lipase-catalyzed perhydrolysis for the formation of peracetic acid, which is the responsible for the ketone oxidation. Optimization studies have been performed in the oxidation of cyclobutanone, finding Candida antarctica lipase type B, ethyl acetate and urea-hydrogen peroxide complex as the best system. The relative ratio of these reagents has also been analyzed in depth. This synthetic approach has been successfully extended to a family of 3-substituted cyclobutanones in high substrate concentration, yielding the corresponding lactones with excellent isolated yields and purities, under mild reaction conditions and after a simple extraction protocol.

NOVEL FXR (NR1H4) BINDING AND ACTIVITY MODULATING COMPOUNDS

The present invention relates to compounds which bind to the NR1H4 receptor (FXR) and act as agonists of FXR. The invention further relates to the use of the compounds for the preparation of a medicament for the treatment of diseases and/or conditions through binding of said nuclear receptor by said compounds and to a process for the synthesis of said compounds.

Novel FXR (NR1H4) binding and activity modulating compounds

The present invention relates to compounds which bind to the NR1H4 receptor (FXR) and act as agonists of the NR1H4 receptor (FXR). The invention further relates to the use of the compounds for the preparation of a medicament for the treatment of diseases and/or conditions through binding of said nuclear receptor by said compounds and to a process for the synthesis of said compounds. wherein R is selected from the group consisting of COOR6, CONR7R8, tetrazolyl, SO2NR7R8, C1-6 alkyl, SO2-C1-6 alkyl and H, with R6 independently selected from the group consisting of H or C1-6 alkyl, and R7 and R8 independently from each other selected from the group consisting of H, C1-6 alkyl, halo-C1-6 alkyl, C1-6 alkylene-R9, SO2-C1-6 alkyl, wherein R9 is selected from the group consisting of COOH, OH and SO3H; A is selected from the group consisting of phenyl, pyridyl, pyrimidyl, pyrazolyl, indolyl, thienyl, benzothienyl, indazolyl, benzisoxazolyl, benzofuranyl, benzotriazolyl, furanyl, benzothiazolyl, thiazolyl, oxadiazolyl, each optionally substituted with one or two groups independently selected from the group consisting of OH, O-C1-6 alkyl, O-halo-C1-6 alkyl, C1-6 alkyl, halo-C1-6 alkyl, C3-6 cycloalkyl and halogen; Q is selected from the group consisting of phenyl, pyridyl, thiazolyl, thiophenyl, pyrimidyl, each optionally substituted with one or two groups independently selected from the group consisting of C1-6 alkyl, halo-C1-6 alkyl, halogen and CF3; Y is selected from N or CH; Z is selected from wherein X= CH, N, NO.

Baeyer-Villiger Oxidation of Cyclobutanones with 10-Methylacridinium as an Efficient Organocatalyst

Baeyer-Villiger oxidation of cyclobutanones is achieved in current developed protocol with 10-methylacridinium perchlorate (AcrH +ClO4-) as a novel organocatalyst both with irradiation at room temperature and without irradiation at elevated temperature. Excellent yields of the corresponding lactones are obtained and the possible mechanism has been proposed.

A convergent radical-based route to biaryls

A route to blaryl-3-carboxylate esters Involving a radical 1,2-aryl migration has been developed. This strategy hinges on the radical addition of xanthate 2 to olefin 1 causing a 1,2-aryl shift leading to α,β- unsaturated ester 5, which Is then converted