28172-58-9

Basic information

• Product Name: 5(4H)-Oxazolone, 2-(4-methoxyphenyl)-4-phenyl-
• CAS NO: 28172-58-9
• Molecular Formula: C16H13NO3
• Molecular Weight: 267.284
• Mol File: 28172-58-9.mol
• Article Data: 13

Chemical Properties

• CAS DataBase Reference: 5(4H)-Oxazolone, 2-(4-methoxyphenyl)-4-phenyl-(CAS DataBase Reference)
• NIST Chemistry Reference: 5(4H)-Oxazolone, 2-(4-methoxyphenyl)-4-phenyl-(28172-58-9)
• EPA Substance Registry System: 5(4H)-Oxazolone, 2-(4-methoxyphenyl)-4-phenyl-(28172-58-9)

Safety Data

• Hazardous Substances Data: 28172-58-9(Hazardous Substances Data)

Upstream product

• 15028-40-7 DL-2-phenylglycine methyl ester hydrochloride 
• 125700-07-4 (4-Methoxy-benzoylamino)-phenyl-acetic acid methyl ester 
• 2835-06-5 phenylglycin 
• 100-07-2 4-methoxy-benzoyl chloride 
• 28172-53-4 DL-2-(4-methoxybenzamido)-2-phenylacetic acid 

Downstream Products

• 110315-03-2 2-(4-methoxyphenyl)-4-phenyl-4-(2,4,6-trinitrophenyl)-5(4H)-oxazolone 
• 50709-69-8 2-(2,4-dinitrophenyl)-4-isopropyl-2-phenyl-5(2H)-oxazolone 
• 110315-04-3 4-<2-(methoxycarbonyl)-4,6-dinitrophenyl>-2-(4-methoxyphenyl)-4-phenyl-5(4H)-oxazolone 
• 110698-99-2 4-[1-(4-Chloro-phenyl)-1H-[1,2,3]triazol-4-ylmethyl]-2-(4-methoxy-phenyl)-4-phenyl-4H-oxazol-5-one 
• 110699-09-7 4-Methoxy-N-(2-morpholin-4-yl-2-oxo-1-phenyl-ethyl)-benzamide 
• 110699-06-4 5-(4-Methoxy-phenyl)-2-phenyl-1H-pyrrole-3-carbaldehyde 
• 110699-11-1 3-[1-(4-Chloro-phenyl)-1H-[1,2,3]triazol-4-yl]-2-(4-methoxy-benzoylamino)-2-phenyl-propionic acid methyl ester 
• 110699-01-9 2-(4-Methoxy-phenyl)-4-phenyl-4-[1-(3-trifluoromethyl-phenyl)-1H-[1,2,3]triazol-4-ylmethyl]-4H-oxazol-5-one 
• 128732-18-3 2-(4-Methoxy-phenyl)-4-phenyl-4-(3-phenyl-isoxazol-4-ylmethyl)-4H-oxazol-5-one 

Relevant articles and documents

Chemoselective activation of sp3 vs sp2 C-H bonds with Pd(II)

The first selective coupling of a carbon nucleophile with methyl, ethyl, propyl, and butyl arenes in the absence of a directing group is described. Pd(OAc)2 double C-H activation displays remarkable selectivity for the terminal methyl sites in alkyl arenes, rather than the more commonly observed arene sp2 C-H activation. Mechanistic studies indicate the intermediacy of an azlactone dimer, obtained from oxidation with Pd(OAc)2, and are consistent with a Pd-catalyzed C-H activation vs a radical process. The observed reactivity establishes that typical reaction solvents (e.g., toluene) can readily participate in C-H activation chemistry.

Amino Acid Schiff Base Bearing Benzophenone Imine As a Platform for Highly Congested Unnatural α-Amino Acid Synthesis

Unnatural α-amino acids are invaluable building blocks in synthetic organic chemistry and could upgrade the function of peptides. We developed a new mode for catalytic activation of amino acid Schiff bases, serving as a platform for highly congested unnatural α-amino acid synthesis. The redox active copper catalyst enabled efficient cross-coupling to construct contiguous tetrasubstituted carbon centers. The broad functional group compatibility highlights the mildness of the present catalysis. Notably, we achieved successive β-functionalization and oxidation of amino acid Schiff bases to afford dehydroalanine derivatives bearing tetrasubstituted carbon. A three-component cross-coupling reaction of an amino acid Schiff base, alkyl bromides, and styrene derivatives demonstrated the high utility of the present method. The diastereoselective reaction was also achieved using menthol derivatives as a chiral auxiliary, delivering enantiomerically enriched α-amino acid bearing α,β-continuous tetrasubstituted carbon. The synthesized highly congested unnatural α-amino acid could be derivatized and incorporated into peptide synthesis.

Strategy for Catalytic Chemoselective Cross-Enolate Coupling Reaction via a Transient Homocoupling Dimer

A new strategy, a transient homocoupling dimer strategy, for direct catalytic oxidative cross-enolate coupling reactions is developed. Cross-enolate coupling products bearing a (contiguous) tetrasubstituted carbon center were obtained chemoselectively without the need for stoichiometric amounts of strong bases/metal oxidants, and thus, the present catalysis provides a general method for the synthesis of unnatural α,α-disubstituted amino acid motifs. The distinct transformation of azlactone and 2-acylimidazole units highlighted the synthetic utility of the present catalysis.