78589-68-1

Basic information

• Product Name: methyl 4-oxo-2-phenyl-4H-chromene-3-carboxylate
• Synonyms: methyl 4-oxo-2-phenyl-4H-chromene-3-carboxylate
• CAS NO: 78589-68-1
• Molecular Weight: 280.28
• Mol File: 78589-68-1.mol

Chemical Properties

• CAS DataBase Reference: methyl 4-oxo-2-phenyl-4H-chromene-3-carboxylate(CAS DataBase Reference)
• NIST Chemistry Reference: methyl 4-oxo-2-phenyl-4H-chromene-3-carboxylate(78589-68-1)
• EPA Substance Registry System: methyl 4-oxo-2-phenyl-4H-chromene-3-carboxylate(78589-68-1)

Safety Data

• Hazardous Substances Data: 78589-68-1(Hazardous Substances Data)

Upstream product

• 67-56-1 methanol 
• 5153-67-3 nitrostyrene 
• 1076-38-6 4-hydroxy[1]benzopyran-2-one 
• 75-52-5 nitromethane 
• 100-52-7 benzaldehyde 
• 425686-45-9 methyl 3-(2-hydroxyphenyl)propiolate 
• 1417564-38-5 C₁₇H₁₄O₄ 
• 1607814-54-9 methyl 2-(3-phenylprop-2-ynoyl)phenyl carbonate 
• 16619-68-4 1-(2-hydroxyphenyl)-3-phenylprop-2-yn-1-one 
• 1002130-71-3 methyl 3-[2-(methoxymethoxy)phenyl]propiolate 
• 78589-61-4 Benzoic acid 2-[2-methoxycarbonyl-2-(triphenyl-λ⁵-phosphanylidene)-acetyl]-phenyl ester 

Downstream Products

• 77037-45-7 4-oxo-2-phenyl-4H-1-benzopyran-3-carboxylic acid 
• 19492-11-6 3-benzoyl-4-hydroxy-2H-chromen-2-one 

Relevant articles and documents

A concise total synthesis of biologically active frutinones via tributylphosphine-catalyzed tandem acyl transfer-cyclization

A concise and step-economical total synthesis of biologically active frutinones has been achieved. Tributylphosphine (PBu3) efficiently induced the tandem acyl transfer-cyclization of carbonates 5 to afford 3-methoxycarbonylflavone derivatives 4 in excellent yields. Finally, concomitant deprotection and lactonization under acidic conditions furnished the desired frutinones A (1a), B (1b), and the proposed structure of frutinone C (1c).

One-pot synthesis of 2-aryl-3-alkoxycarbonyl chromones through a cascade Lewis acid-catalyzed aldehyde olefination/oxa-Michael addition/oxidation

2-Aryl-3-alkoxycarbonyl chromones were effectively constructed from aryl aldehydes and 3-(2-(methoxymethoxy) phenyl)propiolates via a cascade Lewis acid catalyzed phenol ether deprotection/aldehyde olefination/intramolecular oxa-Michael addition reaction, and a sequential oxidation. This four-step reaction could be conducted in one-pot with high atom efficiency.

Alcohol mediated synthesis of 4-oxo-2-aryl-4H-chromene-3-carboxylate derivatives from 4-hydroxycoumarins

The unusual alcohol mediated formation of 4-oxo-2-aryl-4H-chromene-3- carboxylate (flavone-3-carboxylate) derivatives from 4-hydroxycoumarins and β-nitroalkenes in an alcoholic medium is described. The transformation occurs via the in situ formation of a Michael adduct, followed by the alkoxide ion mediated rearrangement of the intermediate. The effect of the different alcohol and nonalcohol media on the reaction was investigated.

NOUVEAU MODE DE CYCLYSATION DE CETO-YLURES. APPLICATION A UNE SYNTHESE IGINALE D'ACYL-3 HYDROXY-4-COUMARINES ET DE L'HYDROXY-11 BENZO-(b) 12 XANTHONE-12

The thermal decomposition of keto-ylides resulting from the reaction of m- and p-acetoxy benzoyl chlorides with Ph3P=CH-COOMe leads, after saponification to m- and p-phenylpropiolic acid respectively.Ortho substitution by an acyl group generally changes the orientation of the reaction.Thus o-acetoxy-, benzoyloxy- or phenylacetoxy benzoyl chlorides respectively afford: and (R=Me,Ph) in satisfactory yields.Saponification of the first and second ones gives: (R=Me, Ph).This constitutes a new, convenient route to 3-acyl 4-hydroxy cumarins and 11-hydroxy 12H-benzoxanthene 12-one.Formation of these last products involves the carbonyl of the acyloxy-substituent and not of the acyl chloride as previously observed in these series.