152714-07-3

Basic information

• Product Name: 3-(4-CHLOROPHENYL)-CYCLOBUTAN-1-ONE
• Synonyms: 3-(4-CHLOROPHENYL)-CYCLOBUTAN-1-ONE;3-(4-CHLOROPHENYL)-CYCLOBUTANE-1-ONE
• CAS NO: 152714-07-3
• Molecular Formula: C₁₀H₉ClO
• Molecular Weight: 180.63
• Mol File: 152714-07-3.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 3-(4-CHLOROPHENYL)-CYCLOBUTAN-1-ONE(CAS DataBase Reference)
• NIST Chemistry Reference: 3-(4-CHLOROPHENYL)-CYCLOBUTAN-1-ONE(152714-07-3)
• EPA Substance Registry System: 3-(4-CHLOROPHENYL)-CYCLOBUTAN-1-ONE(152714-07-3)

Safety Data

• Hazard Codes: Xi
• Hazardous Substances Data: 152714-07-3(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
3-(4-CHLOROPHENYL)-CYCLOBUTAN-1-ONE is used as a synthetic building block for the creation of new compounds, facilitating the development of novel drugs and therapeutic agents. Its unique structural features, including the 4-chlorophenyl group, allow for the introduction of specific characteristics to other molecules, enhancing their pharmacological properties.
Used in Research Applications:
In the field of scientific research, 3-(4-CHLOROPHENYL)-CYCLOBUTAN-1-ONE serves as a precursor in the synthesis of a variety of organic molecules. Its versatility in chemical reactions makes it an essential tool for exploring new chemical pathways and discovering innovative applications in organic chemistry.
Used in Organic Chemistry:
3-(4-CHLOROPHENYL)-CYCLOBUTAN-1-ONE is utilized as a valuable intermediate in organic synthesis, enabling the construction of complex molecular structures. Its presence in the synthesis process can impart specific functional groups and properties to the final product, broadening the scope of chemical compounds that can be synthesized for various applications.
Used in Drug Development:
3-(4-CHLOROPHENYL)-CYCLOBUTAN-1-ONE is employed as a precursor in the development of new drugs, potentially contributing to the discovery of pharmaceuticals with novel mechanisms of action. Its role in the synthesis of drug candidates highlights its importance in advancing the field of medicinal chemistry and drug discovery.

Upstream product

• 104-88-1 4-chlorobenzaldehyde 
• 1073-67-2 4-vinylbenzyl chloride 
• 191019-76-8 2,2-dichloro-3-(4'-chlorophenyl)cyclobutanone 
• 152714-04-0 2-Chloro-3-(4-chloro-phenyl)-cyclobut-2-enone 
• 127-19-5 N,N-dimethyl acetamide 
• 152713-97-8 1-Chloro-4-(2,2-dichloro-3,3-difluoro-cyclobutyl)-benzene 
• 152714-00-6 1-Chloro-4-(2-chloro-3,3-difluoro-cyclobut-1-enyl)-benzene 
• 76-02-8 trifluoroacetyl chloride 

Downstream Products

• 245662-60-6 1-[(3S)-3-(4-chlorophenyl)cyclobut-1-enyloxyl]-1,1-diethyl-1-silapropane 
• 26717-54-4 β-(4-chlorophenyl)-γ-butyrolactone 
• 147224-51-9 β-(R)-(p-chlorophenyl)-γ-butyrolactone 
• 89359-16-0 (S)-β-(4-chlorophenyl)-γ-butyrolactone 
• 22518-27-0 4-(4-chlorophenyl)pyrrolidin-2-one 
• 20697-83-0 3-(4-chlorophenyl)-1-butanol 
• 152714-10-8 (1s,3s)-3-(4-chlorophenyl)cyclobutan-1-ol 
• 152714-14-2 3-(4-Chloro-phenyl)-1-methyl-cyclobutanol 

Relevant articles and documents

A simple and efficient new approach to the total synthesis of (±)-4- amino-3-(4-chlorophenyl)-butyric acid (BACLOFEN)

Based on the utilization of a [2+21 cycloaddition reaction between dichloroketene and an appropriated olefin as a key step, we describe a new and simple four step approach to the total synthesis of (±)-4-amino-3-(4- chlorophenyl)-butyric acid (BACLOFEN),

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.

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.

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.

CARBOXAMIDE AND SULFONAMIDE DERIVATIVES USEFUL AS TEAD MODULATORS

The invention is concerned with the compounds of formula (I) and formula (II): and pharmaceutically acceptable salts thereof. In addition, the present invention relates to methods of using the compounds of formula (I) and formula (II) as well as pharmaceutical compositions containing such compounds. The compounds are useful in treating diseases and conditions mediated by TEAD, such as cancer.

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.

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.

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.).

Synthesis and Physicochemical Properties of 3-Fluorocyclobutylamines

Hitherto unknown cis- and trans-3-alkyl- and 3-aryl-3-fluorocycobutylamines have been synthesised selectively from 3-oxocyclobutane carboxylic acid in six or seven steps. Comparison of their pKa and logD values with those of the fluorine-free p

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.