113567-28-5

Basic information

• Product Name: 4(1H)-Quinolinone, 2,3-dihydro-2-phenyl-, (S)-
• CAS NO: 113567-28-5
• Molecular Formula: C15H13NO
• Molecular Weight: 223.274
• Mol File: 113567-28-5.mol

Chemical Properties

• CAS DataBase Reference: 4(1H)-Quinolinone, 2,3-dihydro-2-phenyl-, (S)-(CAS DataBase Reference)
• NIST Chemistry Reference: 4(1H)-Quinolinone, 2,3-dihydro-2-phenyl-, (S)-(113567-28-5)
• EPA Substance Registry System: 4(1H)-Quinolinone, 2,3-dihydro-2-phenyl-, (S)-(113567-28-5)

Safety Data

• Hazardous Substances Data: 113567-28-5(Hazardous Substances Data)

Upstream product

• 16619-14-0 2-phenyl-2,3-dihydro-1H-quinolin-4-one 
• 1256493-43-2 (S)-2-phenyl-1-tosyl-2,3-dihydroquinolin-4(1H)-one 
• 78396-00-6 1-(2-aminophenyl)-3-phenylprop-2-en-1-one 
• 551-93-9 2-aminoacetophenone 
• 100-52-7 benzaldehyde 
• 4187-87-5 1-Phenyl-2-propyn-1-ol 
• 161117-84-6 tert-butyl 2-iodophenylcarbamate 
• 3066-75-9 allyl diethyl phosphate 
• 1203590-65-1 1-acetyl-2-phenyl-2,3-dihydroquinolin-4(1H)-one 
• 78396-00-6 2-aminochalcone 
• 113544-25-5 2-Oxo-2-{N'-[(S)-2-phenyl-2,3-dihydro-1H-quinolin-(4E)-ylidene]-hydrazino}-N-(1-phenyl-ethyl)-acetamide 

Downstream Products

• 1256493-43-2 (S)-2-phenyl-1-tosyl-2,3-dihydroquinolin-4(1H)-one 

Relevant articles and documents

Primary amino acid catalyzed asymmetric intramolecular Mannich reaction for the synthesis of 2-aryl-2,3-dihydro-4-quinolones

Primary amino acids are found to be good enantioselective catalysts for the direct asymmetric Mannich reaction between 2-amino acetophenone and aldehydes. The 2-aryl-2,3-dihydro-4-quinoline products are obtained in moderate to good yields and good to high enantioselectivities with 10 mol% of the primary amino acid catalyst under mild reaction conditions.

Gold(i) catalyzed tandem cyclization of propargylic esters to 4-acyloxy-1,2-dihydroquinolines

An effective synthetic protocol for structurally diverse 4-acyloxy-1,2-dihydroquinoline compounds has been accomplished by a gold(i)-catalyzed tandem [3,3]-rearrangement and intramolecular hydroamination of propargylic esters, affording the desired products in good yields. Moreover, the asymmetric variant of this cyclization has also been achieved using a chiral nitrogen acyclic carbene (NAC) gold(i) complex. These products have application in the enantioselective synthesis of an aromatase inhibitor within three simple steps.

Organocatalytic one-pot asymmetric synthesis of 2-aryl-2,3-dihydro-4-quinolones

A highly efficient organocatalytic one-pot enantioselective synthesis of (R)-2-aryl-2,3-dihydro-4-quinolones from o-aminoacetophenones and aryl aldehydes has been developed. The approach is characterized by being metal free, solvent free and protecting group free. A variety of 2-aryl-2,3-dihydro-4-quinolones could be obtained in good yields up to 99% ee.

Chiral Phosphoric Acid Catalyzed Asymmetric Synthesis of 2-Substituted 2,3-Dihydro-4-quinolones by a Protecting-Group-Free Approach

Chiral 2-substituted 2,3-dihydro-4-quinolones were synthesized based on the chiral phosphoric acid catalyzed intramolecular aza-Michael addition reaction using N-unprotected 2-aminophenyl vinyl ketones as substrates in good yields with high enantioselectivities. (Chemical Equation Presented).

Per-6-amino-β-cyclodextrin as a chiral base catalyst promoting one-pot asymmetric synthesis of 2-Aryl-2,3-dihydro-4-quinolones

A highly efficient one-pot synthesis of enantiomerically enriched 2-aryl-2,3-dihydroquinolin-4(1H)-ones has been carried out for the first time using per-6-ABCD as a supramolecular host, chiral base catalyst, and a reusable promoter to give the corresponding scaffold with high yield (up to 99%) and enantiomeric excess (up to 99%). The catalyst is recovered and reused without loss in its activity.

One-pot asymmetric synthesis of 2-aryl-2,3-dihydro-4-quinolones catalyzed by amino acid-derived sulfonamides

An organocatalyzed approach to the asymmetric synthesis of 2-aryl-2,3-dihydro-4-quinolones using amino-acid derived sulfonamides as organocatalysts, which can be easily prepared starting from l-proline, l-alanine, and l-phenylalanine, has been developed i

Asymmetric synthesis of 2-Aryl-2,3-dihydro-4-quinolones via bifunctional thiourea-mediated intramolecular cyclization

A novel asymmetric preparation of optically enriched 2-aryl-2,3- dihydroquinolin-4(1H)-ones has been developed. By installing a sulfonyl group on the nitrogen of the anilines and an ester function on the unsaturated ketones, an intramolecular organocataly

Kinetic resolution of 2,3-dihydro-2-substituted 4-quinolones by palladium-catalyzed asymmetric allylic alkylation

(Chemical Equation Presented) The kinetic resolution of a carbon nucleophile is realized for the first time via Pd-catalyzed asymmetric allylic alkylation with "unstabilized" ketone enolates as the nucleophile, providing both allylated 2,3-disubstituted 2

RESOLUTION OF (+/-)-2,3-DIHYDRO-2-PHENYL-4(1H)-QUINOLONE

The resolution of (+/-)-2,3-dihydro-2-phenyl-4(1H)-quinolone into individual enantiomers was achieved using the optically active oxo reagent (-)-5-(α-phenethyl)semioxamazide.The enantiomeric purity was checked by 1H NMR using the chiral lanthanide shift reagent Eu(hfc)3.