36640-12-7

Basic information

• Product Name: 1H-2-Benzopyran-1-one, 8-methoxy-3-(4-methoxyphenyl)-
• CAS NO: 36640-12-7
• Molecular Formula: C17H14O4
• Molecular Weight: 282.296
• Mol File: 36640-12-7.mol
• Article Data: 5

Chemical Properties

• CAS DataBase Reference: 1H-2-Benzopyran-1-one, 8-methoxy-3-(4-methoxyphenyl)-(CAS DataBase Reference)
• NIST Chemistry Reference: 1H-2-Benzopyran-1-one, 8-methoxy-3-(4-methoxyphenyl)-(36640-12-7)
• EPA Substance Registry System: 1H-2-Benzopyran-1-one, 8-methoxy-3-(4-methoxyphenyl)-(36640-12-7)

Safety Data

• Hazardous Substances Data: 36640-12-7(Hazardous Substances Data)

Upstream product

• 1137-31-1 2-carboxy-3-methoxybenzene-1-acetic acid 
• 100-07-2 4-methoxy-benzoyl chloride 
• 42421-12-5 (2-carboxy-3-hydroxyphenyl)acetic acid 
• 115912-88-4 3-<(4-methoxyphenyl)nitromethyl>-7-methoxy-1(3H)-isobenzofuranone 
• 29559-26-0 (p-methoxyphenyl)nitromethane 
• 1214-87-5 methyl (2-carbomethoxy-3-methoxyphenyl)acetate 
• 117970-24-8 3',4-dimethoxydeoxybenzoin ethylene acetal 
• 100-66-3 methoxybenzene 
• 1798-09-0 m-methoxyphenylacetic acid 
• 113345-85-0 3,4'-dimethyl-2-carboxystilbene 
• 113345-84-9 methyl 2-methoxy-6-[2-(4-methoxyphenyl)ethenyl]benzoate 
• 117970-26-0 3',4-dimethoxydeoxybenzoin-2'-carboxylic acid 
• 124-38-9 carbon dioxide 
• 115912-97-5 2-<2-(4-methoxyphenyl)-2-nitroethyl>-7-methoxybenzoic acid 

Downstream Products

• 480-47-7 hydrangenol 
• 82780-51-6 (+/-)-3-(4-methoxyphenyl)-8-methoxy-3,4-dihydroisocoumarin 
• 80458-94-2 3'-Deoxythunberginol A 

Relevant articles and documents

Development of bioactive functions in Hydrangeae Dulcis Folium. VI. Syntheses of thunberginols A and F and their 3'-deoxy-derivatives using regiospecific lactonization of stilbene carboxylic acid: Structures and inhibitory activity on histamine release of hydramacrophyllols A and B

Lactonization reaction of 2-carboxystilbene mediated by copper(II) chloride proceeded regiospecifically to give the five-membered lactone, while the bromolactonizations using N-bromosuccinimide and anodic oxidation were found to furnish the six-membered lactone. Using these regiospecific lactonization reactions as a key step, antiallergic and antimicrobial isocoumarins and the benzylidenephthalides thunberginols A and F and their 3'-deoxyanalogs were synthesized from phyllodulcin and hydrangenol. Two phthalides called hydramacrophyllols A and B were isolated from Hydrangeae Dulcis Folium and their stereostructures were determined on the basis of physicochemical and chemical evidence, which included the syntheses of hydramacrophyllols A and B from hydrangenol by the application of the lactonization method using copper(II) chloride. In addition, hydramacrophyllols A and B were found to exhibit an inhibitory effect on the histamine release from rat peritoneal exudate cells induced by antigen- antibody reaction.

TOTAL SYNTHESIS OF (+/-)-HYDRANGENOL

The title compound 8 has been synthesized in five steps and in about 33percent overall yield from 3-methoxyphenylacetic acid, 1.Acid 1 was condensed with anisole in polyphosphoric acid to give 3',4-dimethoxydeoxybenzoin, 2, which was converted to the ethylene acetal 3.The latter was metallated with buthyllithium and carbonated giving crude 3',4-dimethoxydeoxybenzoin-2'-carboxylic acid, 4, from which 3,4-dihydro-8-methoxy-3-(4'-methoxyphenyl)isocoumarin, 7, was obtained either by reduction with sodium borohydride and dehydration, or dehydration to 8-methoxy-3-(4'-methoxyphenyl)isocoumarin, 6, and catalytic hydrogenation.Finally, demethylation of 6 to 8 was performed with boron tribromide.

Syntheses of antifungal isocoumarins. II. Synthesis and antifungal activity of 3-substituted isocoumarins

-