6345-62-6

Basic information

• Product Name: 6-Hydroxy-7-methoxy-4-methyl-2H-1-benzopyran-2-one
• Synonyms: 6-Hydroxy-7-methoxy-4-methyl-2H-1-benzopyran-2-one
• CAS NO: 6345-62-6
• Molecular Formula: C₁₁H₁₀O₄
• Molecular Weight: 206.19
• Mol File: 6345-62-6.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 411.3°C at 760 mmHg
• Flash Point: 167.1°C
• Appearance: /
• Density: 1.309g/cm³
• Vapor Pressure: 2.37E-07mmHg at 25°C
• Refractive Index: 1.588
• CAS DataBase Reference: 6-Hydroxy-7-methoxy-4-methyl-2H-1-benzopyran-2-one(CAS DataBase Reference)
• NIST Chemistry Reference: 6-Hydroxy-7-methoxy-4-methyl-2H-1-benzopyran-2-one(6345-62-6)
• EPA Substance Registry System: 6-Hydroxy-7-methoxy-4-methyl-2H-1-benzopyran-2-one(6345-62-6)

Safety Data

• Hazardous Substances Data: 6345-62-6(Hazardous Substances Data)

Usage

InChI:InChI=1/C11H10O4/c1-6-3-11(13)15-9-5-10(14-2)8(12)4-7(6)9/h3-5,12H,1-2H3

Upstream product

• 2555-28-4 4-methyl-7-methoxy-2H-1-benzopyran-2-one 
• 529-84-0 6,7-dihydroxy-4-methylcoumarin 
• 77-78-1 dimethyl sulfate 
• 75514-03-3 2-methoxy-p-hydroquinone diacetate 
• 141-97-9 ethyl acetoacetate 
• 74-88-4 methyl iodide 
• 824-46-4 methoxyhydroquinone 
• 121-33-5 vanillin 

Downstream Products

• 172798-42-4 methyl (E)-4,5-dihydroxy-2-methoxy-β-methylcinnamate 
• 1453104-65-8 (E)-5-methoxy-3-(4-methoxybenzylideneamino)-1-(4-methoxyphenyl)-10-methyl-8-oxo-1,8-dihydropyrano[3,2-f]chromene-2-carbonitrile 
• 1453104-64-7 (E)-3-(4-chlorobenzylideneamino)-5-methoxy-1-(4-methoxyphenyl)-10-methyl-8-oxo-1,8-dihydropyrano[3,2-f]chromene-2-carbonitrile 
• 1453104-63-6 (E)-3-(benzylideneamino)-5-methoxy-1-(4-methoxyphenyl)-10-methyl-8-oxo-1,8-dihydropyrano[3,2-f]chromene-2-carbonitrile 
• 1453104-68-1 C₂₃H₁₈N₂O₆ 
• 1453104-67-0 C₂₄H₂₀N₂O₆ 
• 1453104-66-9 N-(2-cyano-5-methoxy-1-(4-methoxyphenyl)-10-methyl-8-oxo-1,8-dihydropyrano[3,2-f]chromen-3-yl)acetamide 
• 1453104-62-5 ethyl 3-amino-5-methoxy-1-(4-methoxyphenyl)-10-methyl-8-oxo-1,8-dihydropyrano[3,2-f]chromene-2-carboxylate 
• 1453104-61-4 ethyl 3-amino-1-(4-chlorophenyl)-5-methoxy-10-methyl-8-oxo-1,8-dihydropyrano[3,2-f]chromene-2-carboxylate 
• 1453104-60-3 ethyl 3-amino-5-methoxy-10-methyl-8-oxo-1-phenyl-1,8-dihydropyrano[3,2-f]chromene-2-carboxylate 
• 1453104-59-0 3-amino-5-methoxy-1-(4-methoxyphenyl)-10-methyl-8-oxo-1,8-dihydropyrano[3,2-f]chromene-2-carbonitrile 
• 1453104-58-9 3-amino-1-(4-chlorophenyl)-5-methoxy-10-methyl-8-oxo-1,8-dihydropyrano[3,2-f]chromene-2-carbonitrile 
• 1453104-57-8 3-amino-5-methoxy-10-methyl-8-oxo-1-phenyl-1,8-dihydropyrano[3,2-f]chromene-2-carbonitrile 
• 4281-40-7 6,7-dimethoxy-4-methylcoumarin 

Relevant articles and documents

Study of the Oxidative Cleavage Proposed in the Biogenesis of Transtaganolides/Basiliolides: Pyran-2-one Aromaticity-Mediated Regioselective Control and Biogenetic Implications

The synthetic feasibility of the oxidative cleavage: epoxidation of 7-O-geranylscopoletin followed by electrocyclic ring-opening, proposed in the biogenesis of transtaganolides/basiliolides is studied. Unlike the proposed pericyclic reactions, this pathway has not yet been addressed. Three synthetic strategies have been tested consisting of: i) Baeyer–Villiger oxidation of p-quinoids, ii) hydrolysis of quinone monoketals, or iii) direct fragmentation by using oxygen donors. Oxidation of the benzene ring of hydroxylated coumarins has been achieved using peroxyacids, but cleavage took place between undesired positions. The aromaticity conservation of the pyran-2-one cycle during oxidation is the controlling factor of these observed regioselectivities. The use of a 4,5-dihydroxy-2-methoxycinnamate model, in which the pyran-2-one ring does not exert influence on oxidation, has allowed the design of a synthetic sequence toward an analogue of the natural pyran-2-one isolated from Thapsia transtagana, key in the biogenesis. Mechanistic proposals for the obtained results as well as their biogenetic implications are raised.

Regioselective Mono-O-alkylation of some Pyrocatechoxide Dianions

In dimethyl sulphoxide the dianions derived from 2,3- or 3,4-dihydroxybenzaldehydes and 4-methylesculetin afford products corresponding to alkylation at the less acidic site while the monoanions give the isomeric phenols.