42436-86-2

Basic information

• Product Name: 2-Phenylcyclobutanone
• Synonyms: 2-Phenylcyclobutanone;2-phenylcyclobutan-1-one;Cyclobutanone, 2-phenyl-
• CAS NO: 42436-86-2
• Molecular Formula: C₁₀H₁₀O
• Molecular Weight: 146.19
• Mol File: 42436-86-2.mol

Chemical Properties

• Appearance: /
• Storage Temp.: -20°C Freezer, Under inert atmosphere
• Solubility: Chloroform (Slightly), Methanol (Slightly)
• CAS DataBase Reference: 2-Phenylcyclobutanone(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Phenylcyclobutanone(42436-86-2)
• EPA Substance Registry System: 2-Phenylcyclobutanone(42436-86-2)

Safety Data

• Hazardous Substances Data: 42436-86-2(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
2-Phenylcyclobutanone is used as a synthetic intermediate for the preparation of various pharmaceutical compounds. Its unique structure allows for the creation of complex molecules with potential therapeutic applications.
Used in Chemical Synthesis:
2-Phenylcyclobutanone is used as a reagent for the green preparation of γ, δand ε-keto esters. These keto esters are important building blocks in the synthesis of various organic compounds, including pharmaceuticals, agrochemicals, and other specialty chemicals.
Used in Flavor and Fragrance Industry:
Due to its unique aromatic properties, 2-Phenylcyclobutanone can be used as a component in the creation of novel fragrances and flavors, adding depth and complexity to the final product.
Used in Material Science:
2-Phenylcyclobutanone's structural characteristics make it a potential candidate for the development of new materials with specific properties, such as improved stability or reactivity in various applications.

Synthesis Reference(s)

Tetrahedron Letters, 36, p. 1667, 1995 DOI: 10.1016/0040-4039(95)00125-V

Upstream product

• 246180-23-4 1-(Hydroxy-phenyl-methyl)-cyclopropanol 
• 100-52-7 benzaldehyde 
• 98-80-6 phenylboronic acid 
• 108-86-1 bromobenzene 
• 1191-95-3 cyclobutanone 
• 36094-39-0 2-Phenyl-1-oxa-spiro[2.2]pentane 
• 39677-54-8 3-phenyl-3,6-dihydro-pyridazine-1,2-dicarboxylic acid diethyl ester 
• 64545-13-7 Phenyl-trimethylsilanyl-acetic acid 
• 770-09-2 benzyltrimethylsilane 
• 33013-65-9 4,5-epoxy-3-phenyl-tetrahydro-pyridazine-1,2-dicarboxylic acid diethyl ester 
• 70042-49-8 α-<1-(phenylthio)cyclopropyl>benzyl alcohol 
• 343272-05-9 1-(methoxyethoxymethoxy)cyclopropanecarboxaldehyde 
• 591-51-5 phenyllithium 
• 186581-53-3 diazomethane 

Downstream Products

• 880551-46-2 dimethyl 2,7-dimethyl-4-phenylbicyclo[6.3.0]undeca-1,7-dien-3-one-10,10-dicarboxylate 
• 1160784-66-6 C₂₂H₂₀Se₂ 
• 64145-51-3 3-phenylcyclopentanone 
• 1198-34-1 2-Phenylcyclopentanone 
• 71172-63-9 4-phenyl-4-methoxybutanenitrile 
• 24241-74-5 (+/-)-4-hydroxy-4-phenylbutanenitrile 
• 5343-98-6 4-oxo-4-phenylbutanenitrile 
• 92243-55-5 2-phenyl-cyclobutanol 
• 2051-95-8 succinylbenzene 
• 10229-11-5 4-phenyl-but-3-yn-1-ol 
• 92499-58-6 2-Diaethylamino-2-phenyl-cyclobutanon-⁽¹⁾ 
• 92321-62-5 2-Diaethylamino-2-phenyl-cyclobutanol-⁽¹⁾ 
• 91904-06-2 2-Dimethylaminomethyl-2-phenyl-cyclobutylamin 

Relevant articles and documents

Oxidative Ring Expansion of Cyclobutanols: Access to Functionalized 1,2-Dioxanes

Cyclobutanols undergo an oxidative ring expansion with Co(acac)2 and triplet oxygen to give 1,2-dioxanols. The formation of an alkoxy radical drives the regioselective cleavage of the ring on the more substituted side before insertion of molecular oxygen. The reaction is particularly effective on secondary cyclobutanols but works also on certain tertiary alcohols. Further substitution with neutral nucleophiles under catalytic Lewis acid conditions led to original 1,2-dioxanes with a preferred 3,6-cis-configuration.

Copper-Catalyzed Enantioselective Arylation via Radical-Mediated C-C Bond Cleavage: Synthesis of Chiral ω,ω-Diaryl Alkyl Nitriles

The first example of copper-catalyzed ring-opening, enantioselective arylation of cyclic ketoxime esters to access ω,ω-diaryl alkyl nitriles has been developed in high yield (up to 92% yield) with excellent enantioselectivity (up to 91% ee). Side-arm bis(oxazoline) ligand plays a significant role in this asymmetric catalytic transformation, which provides an efficient route to construct diverse chiral ω,ω-diaryl alkyl nitriles. Synthetic utility has also been demonstrated in the further derivatization of the ω,ω-diaryl alkyl nitrile to the corresponding amide.

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 2-Substituted Cyclobutanones by a Suzuki Reaction and Dephosphorylation Sequence

We report a novel process for the preparation of 2-substituted cyclobutanones. Such a method relies on the cross-coupling reaction of bromocyclobutenyl diethyl phosphate with either boronic acids or organozinc reagents. Dephosphorylation of the prepared 2-substituted cyclobutenyl phosphates affords 2-substituted cyclobutanones. We observed that the course of the dephosphorylation reaction depends on the properties of the substituents found on the cyclobutene nucleus. The presence of groups capable of stabilizing the negative charge is necessary for ring opening of cyclobutanones. The scope of the reported process for the preparation of 2-substituted cyclobutanones has also been extended to the preparation of cyclobutenyl sulfides.

Radical-Cation Vinylcyclopropane Rearrangements by TiO2Photocatalysis

Radical cation vinylcyclopropane rearrangements by TiO2 photocatalysis in lithium perchlorate/nitromethane solution are described. The reactions are triggered by oxidative single electron transfer, which is followed by immediate ring-opening of the cyclopropanes to generate distonic radical cations as unique reactive intermediates. This approach can also be applied to vinylcyclobutane, leading to the construction of six-membered rings. A stepwise mechanism via distonic radical cations is proposed based on preliminary mechanistic studies, which is supported by density functional theory calculations.

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 FOR THE TREATMENT OF PAIN

Provided herein are compounds that are useful in the treatment of pain in a subject.

Enantioselective Radical Ring-Opening Cyanation of Oxime Esters by Dual Photoredox and Copper Catalysis

Catalytic enantioselective chemical reactions involving highly reactive radical species remain largely unexplored. We report herein for the first time a novel enantioselective radical ring-opening cyanation of redox-active oxime esters by dual photoreodox

Visible light-induced palladium-catalyzed ring opening β-H elimination and addition of cyclobutanone oxime esters

A palladium catalyst under visible light irradiation activates cyclobutanone oxime ester through single electron transfer to induce radical ring opening to generate hybrid cyanoalkyl Pd(i) radical species. Hybrid cyanoalkyl Pd(i) radical species can undergo either β-H elimination to deliver (E)-4-arylbut-3-enenitrile or undergo radical addition with silyl enol ether and enamide to generate δ-cyano ketones. A dual ligand system composed of two phosphine ligands is essential for the high reactivity.

Cu-Catalyzed Redox-Neutral Ring Cleavage of Cycloketone O-Acyl Oximes: Chemodivergent Access to Distal Oxygenated Nitriles

A chemodivergent copper-catalyzed ring opening of cycloketone oximes via radical-mediated C-C bond cleavage under redox-neutral conditions is described. This method allows the divergent synthesis of γ- and δ-acyloxylated, alkoxylated, and hydroxylated nitriles while avoiding the use of toxic cyanide reagents. Moreover, these reactions proceed under very mild conditions with good functional group tolerance. Notably, ring-opening reactions of the less-strained substrate cyclopentanone oxime also proceeded well under the established conditions.