77953-17-4

Upstream product

• 583-06-2 3-benzoylacrylic acid 
• 22536-46-5 2-((2-oxo-2-phenylethyl)thio)acetic acid 
• 65245-10-5 2-hydroxy-4-oxo-4-phenylbutanoic acid 
• 50459-71-7 Ethyl 2-cyano-4-oxo-2-(2-oxo-2-phenylethyl)-4-phenylbutanoate 
• 98-86-2 acetophenone 
• 298-12-4 Glyoxilic acid 
• 90655-57-5 3-phenacyl-5-phenyl-3H-furan-2-one 
• 13505-41-4 4,4,4-trichloro-3-hydroxy-1-phenylbutan-1-one 
• 71198-97-5 1,5-diphenyl-3,3-dimethoxycarbonyl-1,5-pentanedione 
• 3360-54-1 3-bromo-2-phenylprop-1-ene 
• 172980-64-2 methyl 2-(2-oxo-2-phenylethyl)-4-phenylpent-4-enoate 
• 53515-22-3 3-bromo-4-oxo-4-phenylbutanoic acid 
• 172980-58-4 methyl 4,4-dimethoxy-4-phenylbutanoate 
• 25333-24-8 3-benzoylpropionic acid methyl ester 

Downstream Products

• 90655-57-5 3-phenacyl-5-phenyl-3H-furan-2-one 
• 172980-60-8 1-diazo-3-(2-oxo-2-phenylethyl)-5-phenylpentane-2,5-dione 
• 753454-19-2 2,6-diphenyl-4H-pyran-4-carboxylic acid methyl ester 
• 172980-59-5 methyl 4-oxo-2-(2-oxo-2-phenylethyl)-4-phenylbutanoate 
• 874528-17-3 3,4-dihydroxy-3,4-diphenyl-cyclopentanecarboxylic acid 
• 38947-57-8 2,6-diphenyl-isonicotinic acid 

Relevant academic research and scientific papers

1,5-Diaryl-3,3-disubstituted-1,5-pentanedione - A synthon for 2,4,6-trisubstituted heterocycles

2,4,6-Trisubstituted heterocycles are prepared by the functionalization of gem-disubstituents and keto functionalities in 1,5-diaryl-3,3-dimethoxycarbonyl- 1,5-pentane-dione (1) and 1,5-diaryl-3-cyano-3-ethoxycarbonyl-1,5-pentanedione (4).

Ligand-induced selectivity in the rhodium(II)-catalyzed reactions of α-diazo carbonyl compounds

3-Allyl-2,5-diazopentanedione and 3-butenyl-2,5-diazopentanedione were allowed to react with a trace amount of a rhodium(II) catalyst in methylene chloride at room temperature. The major products isolated correspond to the internal trapping of a carbonyl ylide as well as intramolecular cyclopropanation. Changing the catalyst from Rh2(OAc)4 to Rh2(cap)4 to Rh2(tfa)4 caused a significant alteration in product distribution. A rather unusual and unexpected regiochemical crossover in the cycloaddition occurred when Rh2(tfa)4 was used and is most likely due to complexation of the metal with the dipole. A computational approach to rationalize the observed product distribution was carried out. The thermodynamic stabilities of cycloaddition transition states were approximated from the computationally derived strain energies of ground state molecules using traditional force-field techniques. Globally minimized ground state energies were obtained for all possible cycloaddition products, and final strain energies were calculated. In all cases studied, the lower energy isomer corresponded to the cycloadduct actually isolated. A study of the regiochemical aspects of the Rh(II)-catalyzed reaction of 1-diazo-3-(2-oxo-2-phenylethyl)hexane-2,5-dione was also carried out. Cyclization of the initially formed rhodium carbenoid occurred exclusively across the acetyl rather than the benzoyl group. The structure of the internal cycloadduct was assigned on the basis of a proton-detected multiple-bond heteronuclear multiple-quantum coherence experiment.

SYNTHESIS OF SUBSTITUTED 2- AND 4-CARBOXYPYRYLIUM SALTS

Modified methods for the synthesis of substituted 2- and 4-carboxypyrylium perchlorates and the necessary diphenacylacetic acids are proposed.