2860-03-9

Upstream product

• 4487-15-4 benzylidine-2-methoxy-5,6-benzoacetophenone 
• 40649-77-2 3-phenyl-1-(2'-hydroxynaphthyl)-2-propen-1-one 
• 40649-77-2 (E)-1-(2-hydroxynaphthalen-1-yl)-3-phenylprop-2-en-1-one 
• 76339-56-5 2-naphthylcinnamate 
• 75-15-0 carbon disulfide 
• 7446-70-0 aluminium trichloride 
• 621-82-9 Cinnamic acid 
• 93-04-9 2-Methoxynaphthalene 
• 941-98-0 1'-naphthacetophenone 
• 100-52-7 benzaldehyde 
• 88034-35-9 pentacarbonyl{1-(1-methoxy-3(E)-phenyl-2-propenylidene)}chromium⁽⁰⁾ 
• 1076-26-2 1-methyl-2-naphthol 
• 135-19-3 β-naphthol 
• 60983-66-6 2'-difluoroboroxy-5',6'-benzochalcone 

Downstream Products

• 6051-87-2 3-phenyl-1H-naphtho[2,1-b]pyran-1-one 
• 40649-77-2 (E)-1-(2-hydroxynaphthalen-1-yl)-3-phenylprop-2-en-1-one 
• 166761-74-6 3-(2-hydroxy-1-naphthyl)-5-(phenyl)-2-isoxazoline 
• 1413433-51-8 C₁₉H₁₄O₂ 
• 40649-77-2 3-phenyl-1-(2'-hydroxynaphthyl)-2-propen-1-one 
• 152598-54-4 Co(OC₁₀H₆C₃H₄N₂C₆H₅)2(C₅H₅N)2 
• 152579-16-3 Ni(OC₁₀H₆C₃H₄N₂C₆H₅)2(C₅H₅N)2 
• 152579-10-7 Cu(OC₁₀H₆C₃H₄N₂C₆H₅)2 
• 152579-19-6 Co(OC₁₀H₆C₃H₄N₂C₆H₅)2(H₂O)2 
• 152598-57-7 Zn(OC₁₀H₆C₃H₄N₂C₆H₅)2 

Relevant academic research and scientific papers

Convenient synthesis of flavanone derivatives via oxa-Michael addition using catalytic amount of aqueous cesium fluoride

A total of 36 flavanones, which included polycyclic aromatic and heterocyclic rings, were readily synthesized via oxa-Michael addition from the corresponding hydroxychalcones with a catalytic amount of aqueous cesium fluoride solution under mild conditions. This method could be applied to the scalable synthesis of eriodictyol as a known potent inhibitor of the SARS-CoV-2 spike protein.

Palladium-Catalyzed [3+3] Annulation of Vinyl Chromium(0) Carbene Complexes through Carbene Migratory Insertion/Tsuji–Trost Reaction

Vinyl chromium(0) Fischer carbene complexes were employed as the source of π-allylic palladium species for catalytic [3+3] annulation under palladium catalysis. Mechanistically, this transformation is proposed to involve carbene migratory insertion and intramolecular Tsuji–Trost reaction as the key steps. Substituted six-membered heterocyclic flavonones and quinolines are obtained, depending on the nucleophilic functional group on the coupling partners.

Extended Aromatic and Heteroaromatic Ring Systems in the Chalcone-Flavanone Molecular Switch Scaffold

Previous work on the o-hydroxychalcone/flavanone molecular switching scaffold showed that simple substitutions alter the pH range in which rapid interconversion occurs. Herein, more impactful structural modifications were performed via alteration of the characteristic phenyl rings to alternative aromatic systems. It was determined that the scaffold was still viable after these changes and that the range of accessible midpoint pH values was markedly increased. To further explore the switch's scope, scaffolds able to have multiple switching events were also investigated.

Microwave-assisted synthesis of chalcones, flavanones and 2-pyrazolines: Theoretical and experimental study

Condensation of 2-acetyl-1-naphthol and 1-acetyl-2-naphthol with benzaldehydes under microwave irradiation gave chalcones or flavanones depending on the type of ketone. Also, 2-pyrazolines were synthesized by the condensation of chalcones with phenyl hydrazine under microwave irradiation in presence of dry acetic acid as a cyclizing agent. The results obtained indicated that, unlike classical heating, microwave irradiation resulted in higher yields, shorter reaction times and cleaner reactions. The structures of the synthesized compounds were elucidated using various spectroscopic methods. Theoretical studies explained the behaviour and reactivity observed for 1-acetyl-2-naphthol with benzaldehydes considering geometries, and electron densities of the formed flavanones.

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.

Solution phase photocyclisation reaction of 2-hydroxychalcones to 4-flavanones

The photochemical cyclisation of 2-hydroxychalcones leading to the synthesis of 4-flavanones in solution phase has been investigated. The formation of photoproducts has been explained on the basis of excited state intramolecular proton transfer (ESIPT) and the cyclisation efficiency of the chalcones has been found to depend upon the electron density on the phenolic oxygen as well as on the carbonyl group. This synthesis of flavanones by photoirradiation is an eco-friendly route with comparative yield to those of thermal methods. Although the molecular skeletons of these substrates is amenable to cis-trans isomerisations and cycloadditions but no photoproducts corresponding to these reactions have been realized.

The Kinetics and Mechanism of the Cyclisation of Some 2'-Hydroxychalcones to Flavanones in Basic Aqueous Solution

Rate coefficients for the chalcone-flavanone equilibration reaction have been established for some 2'-hydroxychalcones over the pH range (ca. 8-11) in which their 2'-hydroxy-groups undergo ionisation.The chalcones studied were the parent 2'-hydroxychalcone (I) and its following derivatives: 4'-OMe (II), 6'-OMe (III), 4'-OH (IV), 4',6'-Me2 (V), and 5',6'-benzo (VI).Pseudo-first-order rate coefficients (kobs) which, for the reversible reactions concerned, are the sum of the forward and reverse rate coefficients, were fitted to the kinetic form, kobs=kfA+k'fB+k''aOH- in which k and k' are the rate coefficients for the unimolecular cyclisation of neutral and of ionised chalcones respectively (fA and fB are the fractions of total chalcone present in the neutral and ionised forms at the pH concerned) and where k'' is the second-order rate coefficient for the reverse reaction of flavanone which involves hydroxide ion (activity aOH-).Data analysis gave rate coefficients and pKa values for all but chalcone (IV) which has a different kinetic form.A conjugate addition-elimination mechanism is proposed to account for the pH-rate profiles, one of which differs from that previously reported.Possible effects on rate coefficients of non-bonded interactions between 6'-substituents and carbonyl oxygen are briefly considered but the differences between chalcones with and without 6'-substituents are sufficiently small to deter prolonged discussion.There seems to be little serious hindrance of cyclisation for any of the 6'-substituted chalcone anions.

n-Butylamine Catalysed Conversion of 2'-Hydroxychalkones into Flavanones

Isomerisation of 2'-hydroxychalkones (Ia-f) to flavanones (IIa-f) in boiling ethanol in the presence of catalytic amount of n-butylamine is described.