57740-69-9

Basic information

• Product Name: 2H-Pyran-2,5(6H)-dione, 3-hydroxy-4-phenyl-6-(phenylmethylene)-
• CAS NO: 57740-69-9
• Molecular Formula: C18H12O4
• Molecular Weight: 292.291
• Mol File: 57740-69-9.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: 2H-Pyran-2,5(6H)-dione, 3-hydroxy-4-phenyl-6-(phenylmethylene)-(CAS DataBase Reference)
• NIST Chemistry Reference: 2H-Pyran-2,5(6H)-dione, 3-hydroxy-4-phenyl-6-(phenylmethylene)-(57740-69-9)
• EPA Substance Registry System: 2H-Pyran-2,5(6H)-dione, 3-hydroxy-4-phenyl-6-(phenylmethylene)-(57740-69-9)

Safety Data

• Hazardous Substances Data: 57740-69-9(Hazardous Substances Data)

Upstream product

• 1589-82-8 phenylmagnesium bromide 
• 100-44-7 benzyl chloride 
• 137532-11-7 3-oxo-1,4-diphenylbutan-2-yl ethyl oxalate 
• 6838-54-6 3-hydroxy-1,4-diphenyl-2-butanone 
• 103-80-0 phenylacetyl chloride 
• 57740-65-5 Oxalsaeure-(ethyl)(2-oxo-3-phenylpropyl)ester 
• 20772-12-7 1-bromo-3-phenyl-2-propanone 
• 57740-67-7 3,4-dehydro-3-hydroxy-5-oxo-4-phenyl-δ-valerolactone 
• 100-52-7 benzaldehyde 
• 131146-48-0 3-methoxy-4-phenyl-6-(phenylmethylene)-2H-pyran-2,5(6H)-dione 
• 131146-47-9 6-bromo-3-methoxy-4-phenyl-6-(phenylmethyl)-2H-pyran-2,5(6H)-dione 
• 131146-44-6 3-methoxy-4-phenyl-6-(phenylmethyl)-2H-pyran-2,5(6H)-dione 
• 131146-41-3 3-hydroxy-4-phenyl-6-(phenylmethyl)-2H-pyran-2,5(6H)-dione 
• 93554-96-2 α-<(trimethylsilyl)oxy>benzenepropanenitrile 

Downstream Products

• 137532-17-3 3-(4-aminophenyl)-5-hydroxy-4,7-diphenylbenzofuran-2,6-dione 
• 6273-79-6 Pulvinic acid lacton 
• 26548-70-9 (E)-5-(α-carboxybenzylidene)-4-hydroxy-3-phenylfuran-2(5H)-one 
• 7611-34-9 xylerythrin 
• 114590-95-3 5-hydroxy-3,4,7-triphenylbenzofuran-2,6-dione 
• 22628-22-4 (E)-4-methoxy-5-(α-methoxycarbonylbenzylidene)-3-phenylfuran-2(5H)-one 
• 521-52-8 vulpic acid 
• 548-59-4 2,5-dihydroxy-3,6-diphenyl-1,4-benzoquinone 

Relevant articles and documents

Synthesis of Grevillins, Novel Pyrandione Pigments of Fungi. Biogenetic Interrelationships between Grevillins, Pulvinic Acids, Terphenylquinones and Xylerythrins

A synthesis of the grevillin group of pyrandione pigments, e.g. 3, 23 and 24 present in fungi is described.The synthesis, which is based on a biogenetic model, uses bis-benzylacyloins 9 and their corresponding oxalate derivatives as key intermediates (Scheme 3).Treatment of the grevillins 25a-c with sodium ethoxide in ethanol effects their quantitative isomerisation into the corresponding terphenylquinone pigments 4a-c.Perkin-type condensations between the terphenylquinones 4 and arylacetic acids in the presence of sodium acetate-acetic anhydride then produces the xylerythrin pigments 29a-e, whereas rearrangements of 4 in the presence of dimethyl sulphoxide leads to pulvinic acid derivative, e.g. 31, 32 and 5.These synthetic studies interrelate the biosynthetic origins of the pigment types 3, 4, 5 and 8 together with the related pulvinones 6 and furanone 7 fungal pigments.

Fungal Pigments, 49. - Synthesis of Grevillins and Related 2H-Pyran-2,5(6H)-diones

A convergent synthesis of grevillins 1 starts from diazoesters 6 which are converted into 3-aryl-2-oxopropyl ethyl oxalates 4 via bromoketones 7.Cyclization of 4 leads to pyrandiones 2 which are condensed with aromatic aldehydes to yield 4-aryl-2-benzylid