151990-53-3

Basic information

• Product Name: 3-Methyl-3-phenylcyclobutanone
• Synonyms: 3-Methyl-3-phenylcyclobutanone
• CAS NO: 151990-53-3
• Molecular Formula: C₁₁H₁₂O
• Molecular Weight: 160
• Mol File: 151990-53-3.mol

Chemical Properties

• Boiling Point: 258℃
• Flash Point: 104℃
• Appearance: /
• Density: 1.067
• CAS DataBase Reference: 3-Methyl-3-phenylcyclobutanone(CAS DataBase Reference)
• NIST Chemistry Reference: 3-Methyl-3-phenylcyclobutanone(151990-53-3)
• EPA Substance Registry System: 3-Methyl-3-phenylcyclobutanone(151990-53-3)

Safety Data

• Hazardous Substances Data: 151990-53-3(Hazardous Substances Data)

Usage

Uses

Used in Food Industry:
3-Methyl-3-phenylcyclobutanone is used as a flavoring agent for its fruity, raspberry-like flavor, enhancing the taste profiles of various food products.
Used in Perfumery and Fragrance Industry:
Leveraging its aromatic characteristics, 3-Methyl-3-phenylcyclobutanone is utilized in the production of perfumes and other fragrance applications, contributing to the creation of complex and appealing scents.
Used in Pharmaceutical Research:
3-Methyl-3-phenylcyclobutanone is studied for its potential therapeutic properties, particularly its ability to inhibit the growth of certain cancer cells. However, further research is necessary to fully explore its medicinal potential and safety profile.

Upstream product

• 136527-27-0 2,2-dichloro-3-methyl-3-phenylcyclobutan-1-one 
• 98-83-9 isopropenylbenzene 
• 98-86-2 acetophenone 
• 4279-76-9 phenoxyacetylene 
• 76-02-8 trifluoroacetyl chloride 

Downstream Products

• 85662-51-7 (rac)-3-phenyl-3-methylcyclopentanone 
• 827-69-0 (E)-4-phenyl-3-penten-2-one 
• 880551-39-3 2,5,7-trimethyl-5-phenylbicyclo[6.3.0]undeca-1,7-dien-3-one 
• 880551-37-1 dimethyl 5-methyl-5-phenylbicyclo[6.3.0]undeca-1,7-dien-3-one-10,10-dicarboxylate 
• 880551-41-7 2,5,7-trimethyl-5-phenyl-10-oxabicyclo[6.3.0]undeca-1,7-dien-3-one 
• 880551-32-6 dimethyl 2,5,7-trimethyl-5-phenylbicyclo[6.3.0]undeca-1,7-dien-3-one-10,10-dicarboxylate 
• 880551-44-0 dimethyl 2,5-dimethyl-5-phenylbicyclo[6.3.0]undeca-1,7-dien-3-one-10,10-dicarboxylate 
• 880551-45-1 dimethyl 5,7-dimethyl-5-phenylbicyclo[6.3.0]undeca-1,7-dien-3-one-10,10-dicarboxylate 
• 880551-42-8 10-(4-tolylsulfonyl)-2,5,7-trimethyl-5-phenyl-10-azabicyclo[6.3.0]undeca-1,7-dien-3-one 
• 880551-40-6 10,10-bis(methoxymethyl)-2,5,7-trimethyl-5-phenylbicyclo[6.3.0]undeca-1,7-dien-3-one 
• 880551-38-2 dimethyl 2,7-diethyl-5-methyl-5-phenylbicyclo[6.3.0]undeca-1,7-dien-3-one-10,10-dicarboxylate 
• 1357271-42-1 1-(2-bromophenyl)-3-methyl-3-phenylcyclobutanol 

Relevant articles and documents

Palladium-Catalyzed Carbene Coupling Reactions of Cyclobutanone N-Sulfonylhydrazones

Described herein are the palladium-catalyzed cross-coupling reactions of cyclobutanone-derived N-sulfonylhydrazones with aryl or benzyl halides, suggesting that the metal carbene process and β-hydride elimination can smoothly occur in strained ring system

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.

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.

Lewis Acid Catalyzed Ring-Opening Reaction of Cyclobutanones towards Conjugated Enones

An unprecedented Fe-catalyzed ring-opening reaction of simple cyclobutanones is developed, which provides access to conjugated enones with good functional group tolerance in high yields under mild conditions. The product derivatization and gram-scale expe

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.

Absence of Intermediates in the BINOL-Derived Mg(II)/Phosphate-Catalyzed Desymmetrizative Ring Expansion of 1-Vinylcyclobutanols

The catalyzed desymmetrizative ring expansion of alkenylcyclobutanols promoted by halofunctionalization of the alkene moiety with N-bromosuccinimide has been experimentally and computationally studied. The reaction yields highly enantioenriched cyclopenta

Synthesis of Cyclobutanones by Gold(I)-Catalyzed [2 + 2] Cycloaddition of Ynol Ethers with Alkenes

A broad scope synthesis of cyclobutanones by gold(I)-catalyzed [2 + 2] cycloaddition of ynol ethers with alkenes has been developed. We also found that internal aryl ynol ethers can undergo (4 + 2) cycloaddition reaction with alkenes leading to the corres

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.