1413433-55-2

Basic information

• Product Name: C₁₉H₁₄O₂
• Synonyms: C₁₉H₁₄O₂
• CAS NO: 1413433-55-2
• Molecular Weight: 274.319
• Mol File: 1413433-55-2.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: C₁₉H₁₄O₂(CAS DataBase Reference)
• NIST Chemistry Reference: C₁₉H₁₄O₂(1413433-55-2)
• EPA Substance Registry System: C₁₉H₁₄O₂(1413433-55-2)

Safety Data

• Hazardous Substances Data: 1413433-55-2(Hazardous Substances Data)

Upstream product

• 125574-15-4 1-hydroxy-2-naphthyl styryl ketone 
• 3262-89-3 triphenylboroxine 
• 3528-23-2 4H-benzo[h]chromen-4-one 
• 711-79-5 1-hydroxy-2-acetonaphthone 

Relevant articles and documents

Preparation method of chiral flavanone

The invention relates to the technical field related to flavonoid compounds, and particularly provides a preparation method of chiral flavanone. The first aspect of the invention provides a preparation method of chiral flavanone, which comprises the following steps: carrying out hydroacylation reaction on salicylaldehyde of which the hydroxyl is vinylated as shown in the formula (1) under the action of transition metal and chiral ligand to form a chiral flavanone compound as shown in the formula (2); wherein the R and R1 in the formula (1) and the formula (2) are independently hydrogen, alkylor aryl respectively, and the R' is any one of hydrogen, alkyl, aryl, alkoxy, aryloxy, ester group, nitro, halogen, cyano, benzyl and heterocyclic substituent.

Asymmetric ion-pairing catalysis of the reversible cyclization of 2'-hydroxychalcone to flavanone: Asymmetric catalysis of an equilibrating reaction

The asymmetric catalytic cyclization of the simple 2'-hydroxychalcone (1) to flavanone (2), a model for the chalcone isomerase reaction, has been realized as a catalytic asymmetric ion-pairing process with chiral quaternary ammonium salts (e.g., 9-anthracenylmethlycinchoninium chloride; 9-Am-CN-Cl) and NaH as small-molecule co-catalyst. In toluene/CHCl3 solution, the process reaches an intrinsic enantioselectivity of up to S = 14.4 (er = 93.5:6.5). The reversible reaction proceeds in two steps: A fast initial reaction approaches a quasi-equilibrium with KR/S = 4.5, followed by a second, slow racemization phase approaching Krac = 9. A simple mechanistic model featuring a living ion-pairing catalysis with full reversibility is proposed. Deuterium transfer from co-solvent CDCl3 to product 2 and isolation of a Michael conjugate formed from 2 and 1 demonstrate the intermediacy of flavanone enolate ion pairs. A kinetic model shows good agreement with the experimentally observed, peculiar, time-dependent evolution of the species concentrations and the enantiomeric excess of 2. The reaction is a chemical model of the chalcone isomerase enzymatic reaction. Furthermore, it is an ideal model for studying the characteristic behavior of reversible asymmetric catalyses close to their equilibria.