65745-74-6

Basic information

• Product Name: 2(1H)-Quinolinone,1-(phenylmethyl)-(9CI)
• Synonyms: 2(1H)-Quinolinone,1-(phenylmethyl)-(9CI);1-Benzyl-1,2-dihydroquinoline-2-one;1-Benzyl-2(1H)-quinolone;1-Benzylquinolin-2(1H)-one
• CAS NO: 65745-74-6
• Molecular Formula: C₁₆H₁₃NO
• Molecular Weight: 235.28
• Product Categories: QUINOLINONE
• Mol File: 65745-74-6.mol
• Article Data: 18

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 2(1H)-Quinolinone,1-(phenylmethyl)-(9CI)(CAS DataBase Reference)
• NIST Chemistry Reference: 2(1H)-Quinolinone,1-(phenylmethyl)-(9CI)(65745-74-6)
• EPA Substance Registry System: 2(1H)-Quinolinone,1-(phenylmethyl)-(9CI)(65745-74-6)

Safety Data

• Hazardous Substances Data: 65745-74-6(Hazardous Substances Data)

Usage

Chemical Family

Quinolinones

Core Structure

Quinolinone

Substituent

Phenylmethyl group

Synthetic and Industrial Applications

Building block in the synthesis of pharmaceuticals, agrochemicals, and specialty chemicals

Intermediate in Production

Dyes, pigments, and polymers

Biological Activities and Pharmacological Properties

Potential for medicinal chemistry research

Upstream product

• 195141-05-0 2-(benzyloxy)quinoline 
• 100-39-0 benzyl bromide 
• 15619-48-4 1-benzylquinolin-1-ium chloride 
• 59-31-4 2-quinolone 
• 100-44-7 benzyl chloride 
• 1035669-83-0 C₁₈H₁₇NO 
• 108-88-3 toluene 
• 91-22-5 quinoline 
• 59-31-4 2-hydroxyquinoline 
• 26323-01-3 1-benz-ylquinolin-1-ium bromide 
• 102-92-1 Cinnamoyl chloride 
• 3056-73-3 N-phenylcinnamamide 

Downstream Products

• 22971-20-6 1-benzyl-2(1H)-thioquinolone 
• 890138-48-4 2-[bis(acetyl)methylene]-1-benzyl-1,2-dihydroquinoline 
• 890138-47-3 2-[acetyl(methoxycarbonyl)methylene]-1-benzyl-1,2-dihydroquinoline 
• 890138-43-9 1-benzyl-1,2-dihydro-2-[bis(methoxycarbonyl)methylene]quinoline 

Relevant articles and documents

Visible light-induced one-pot synthesis of CF3/CF2-substituted cyclobutene derivatives

An efficient one-pot approach for the controllable synthesis of trifluoromethyl/gem-difluoromethylene substituted cyclobutene derivatives has been developed. The mechanism may involve visible light-induced [2+2]-cycloaddition of quinolinones with 1-bromo-1-trifluoromethylethene, followed by base-promoted dehydrobromination, [1,3]-H shift and further dehydrofluorination. A variety of CF3/CF2-substituted cyclobutenes that are currently difficult to obtain are afforded in good yields in this protocol, which may find its way into future fluorinated cyclobutene preparation.

Identification of N-acyl quinolin-2(1H)-ones as new selective agents against clinical isolates of Acanthamoeba keratitis

A collection of N-substituted quinolin-2(1H)-ones were screened against a panel of clinically relevant protozoa (Leishmania, Trypanosoma and Acanthamoeba). Three quinolin-2(1H)-one compounds were identified as selective anti-Acanthamoeba agents. Further assessment revealed that these compounds were active against both trophozoite and cyst forms of A. castellanii Neff, and caused protozoa death via apoptosis. The data presented herein identify N-acyl quinolin-2(1H)-ones as a promising new class of selective anti-Acanthamoeba agents.

Highly Enantioselective Catalytic Addition of Grignard Reagents to N-Heterocyclic Acceptors

General methods to prepare chiral N-heterocyclic molecular scaffolds are greatly sought after because of their significance in medicinal chemistry. Described here is the first general catalytic methodology to access a wide variety of chiral 2- and 4-substituted tetrahydro-quinolones, dihydro-4-pyridones, and piperidones with excellent yields and enantioselectivities, utilizing a single catalyst system.