5685-39-2

Basic information

• Product Name: phenyl(1-phenylcyclopropyl)methanone
• CAS NO: 5685-39-2
• Molecular Formula: C₁₆H₁₄O
• Molecular Weight: 222.2818
• Mol File: 5685-39-2.mol
• Article Data: 9

Chemical Properties

• Boiling Point: 351.8°C at 760 mmHg
• Flash Point: 152.1°C
• Density: 1.152g/cm³
• Vapor Pressure: 4.01E-05mmHg at 25°C
• Refractive Index: 1.62
• CAS DataBase Reference: phenyl(1-phenylcyclopropyl)methanone(CAS DataBase Reference)
• NIST Chemistry Reference: phenyl(1-phenylcyclopropyl)methanone(5685-39-2)
• EPA Substance Registry System: phenyl(1-phenylcyclopropyl)methanone(5685-39-2)

Safety Data

• Hazardous Substances Data: 5685-39-2(Hazardous Substances Data)

Usage

General Description

Phenyl(1-phenylcyclopropyl)methanone, also known as PACMK, is a chemical compound with a complex structure consisting of a phenyl group attached to a cyclopropyl ring, which in turn is connected to a methanone group. phenyl(1-phenylcyclopropyl)methanone is a ketone derivative and belongs to the class of arylcyclopropyl ketones. PACMK has been studied for its potential pharmacological properties, particularly as a potential drug candidate for treating various neurological disorders. Its unique structure and properties make it a promising candidate for further research and development in the field of medicinal chemistry.

Upstream product

• 935-44-4 1-cyano-1-phenylcyclopropane 
• 451-40-1 phenyl benzyl ketone 
• 107-04-0 1-Bromo-2-chloroethane 
• 70775-39-2 dimethylsulfoxonium methylide 
• 1484-50-0 desyl bromide 
• 20144-21-2 Dimethyl-<4-oxo-3,4-diphenyl-butyl>-sulfonium 
• 3306-02-3 1,2-diphenyl-1-cyclobutene 
• 42540-65-8 6,7,7-triphenyl-4,5,6-triaza-spiro[2.4]hept-4-ene 
• 140-29-4 phenylacetonitrile 
• 876511-09-0 (+)-4-methylsulfanyl-1.2-diphenyl-butanone-⁽¹⁾ 
• 93433-92-2 1,2-Diphenyl-1,2-cyclobutandiol 
• 495-71-6 phenacylacetophenone 
• 4452-11-3 1,2-diphenylprop-2-en-1-one 
• 75-11-6 diiodomethane 

Downstream Products

• 63817-67-4 α,1-Diphenylcyclopropanmethanol 
• 5680-55-7 cis-1,4-Dichlor-1,2-diphenyl-but-1-en 
• 5680-56-8 Dichlor-phenyl-<1-phenyl-cyclopropyl>-methan 
• 54444-11-0 cis-2-phenyl-3-methylindanone 
• 3306-02-3 1,2-diphenyl-1-cyclobutene 
• 107627-03-2 1-(1-Phenyl-cyclopropyl)-1-phenyl-propandiol-(1,3) 

Relevant articles and documents

Bromomethyl Silicate: A Robust Methylene Transfer Reagent for Radical-Polar Crossover Cyclopropanation of Alkenes

A general protocol for visible-light-induced cyclopropanation of alkenes was developed with bromomethyl silicate as a methylene transfer reagent, offering a robust tool for accessing highly valuable cyclopropanes. In addition to α-aryl or methyl-substituted Michael acceptors and styrene derivatives, the unactivated 1,1-dialkyl ethylenes were also shown to be viable substrates. Apart from realizing the cyclopropanation of terminal alkenes, the methyl transfer reaction has been further demonstrated to be amenable to the internal olefins. The photocatalytic cyclopropanation of 1,3-bis(1-arylethenyl)benzenes was also achieved, giving polycyclopropane derivatives in excellent yields. With late-stage cyclopropanation as the key strategy, the synthetic utility of this transformation was also demonstrated by the total synthesis of LG100268.

Oxidative Ring Contraction of Cyclobutenes: General Approach to Cyclopropylketones including Mechanistic Insights

An original oxidative ring contraction of easily accessible cyclobutene derivatives for the selective formation of cyclopropylketones (CPKs) under atmospheric conditions is reported. Comprehensive mechanistic studies are proposed to support this novel, yet unusual, rearrangement. Insights into the mechanism ultimately led to simplification and generalization of the ring contraction of cyclobutenes using mCPBA as an oxidant. This unique and functional group tolerant transformation proceeds under mild conditions at room temperature, providing access to a new library of polyfunctionalized motifs. With CPKs being attractive and privileged pharmacophores, the elaboration of such a simple and straightforward strategy represents a highly valuable tool for drug discovery and medicinal chemistry. Additionally, the described method was employed to generate a pool of bioactive substances and key precursors in a minimum number of steps.

Polymer-mediated pinacol rearrangements

Both poly(3,4-ethylenedioxythiophene) and poly(pyrrole) mediate a pinacol rearrangement of 1,2-diols. The yields of ketone or aldehyde products are comparable to those observed for treatment with mineral acids or Lewis acids. The advantage of this protocol is a two-phase reaction medium in hydrocarbon solvents that allows facile recovery of the products by simple filtration of the polymer and removal of solvents. Both the polymer and the hydrocarbon solvent may be recovered and used in subsequent reactions. Georg Thieme Verlag Stuttgart · New York.