82780-51-6

Basic information

• Product Name: (+/-)-3-(4-methoxyphenyl)-8-methoxy-3,4-dihydroisocoumarin
• Synonyms: (+/-)-3-(4-methoxyphenyl)-8-methoxy-3,4-dihydroisocoumarin
• CAS NO: 82780-51-6
• Molecular Weight: 284.312
• Mol File: 82780-51-6.mol
• Article Data: 9

Chemical Properties

• CAS DataBase Reference: (+/-)-3-(4-methoxyphenyl)-8-methoxy-3,4-dihydroisocoumarin(CAS DataBase Reference)
• NIST Chemistry Reference: (+/-)-3-(4-methoxyphenyl)-8-methoxy-3,4-dihydroisocoumarin(82780-51-6)
• EPA Substance Registry System: (+/-)-3-(4-methoxyphenyl)-8-methoxy-3,4-dihydroisocoumarin(82780-51-6)

Safety Data

• Hazardous Substances Data: 82780-51-6(Hazardous Substances Data)

Upstream product

• 113345-85-0 3,4'-dimethylstilbene-2-carboxylic acid 
• 123-11-5 4-methoxy-benzaldehyde 
• 82780-48-1 N,N-Dimethyl-2-methoxy-6-methylbenzamide 
• 7291-34-1 2-methoxy-N,N-dimethylbenzamide 
• 3462-97-3 (4-methoxybenzyl)triphenylphosphonium bromide 
• 53015-08-0 2-formyl-6-methoxy-benzoic acid 
• 66947-61-3 5-methoxybicyclo[4.2.0]octa-1,3,5-trien-7-ol 
• 117970-24-8 3',4-dimethoxydeoxybenzoin ethylene acetal 
• 100-66-3 methoxybenzene 
• 1798-09-0 m-methoxyphenylacetic acid 
• 79383-44-1 methyl 2-methyl-6-methoxybenzoate 
• 943595-13-9 methyl 2-(bromomethoxy)-6-methoxybenzoate 
• 117970-26-0 3',4-dimethoxydeoxybenzoin-2'-carboxylic acid 
• 36640-12-7 3-(4-methoxyphenyl)-7-methoxy-2-benzopyran-1(1H)-one 

Downstream Products

• 480-47-7 hydrangenol 
• 52213-49-7 (+/-)-3-(4-methoxyphenyl)-8-hydroxy-3,4-dihydroisocoumarin 
• 113345-85-0 3,4'-dimethyl-2-carboxystilbene 
• 55555-33-4 phyllodulcin 

Relevant articles and documents

Titanocene(III) chloride mediated radical-induced synthesis of 3,4-dihydroisocoumarins: synthesis of (±)-hydrangenol, (±)-phyllodulcin, (±)-macrophyllol and (±)-thunberginol G

A radical-promoted synthesis of 3,4-dihydroisocoumarins has been achieved in moderate to good yields using titanocene(III) chloride (Cp2TiCl) as the radical initiator. The total synthesis of four naturally occurring dihydrocoumarins hydrangenol, phyllodulcin, macrophyllol and thunberginol G has been accomplished using the radical technology. Cp2TiCl was prepared in situ from commercially available titanocene dichloride (Cp2TiCl2) and Zn-dust in THF under argon.

Reaction of Benzocyclobutenoxides with Aldehydes: Synthesis of Peshawarine and Other 3,4-Dihydroisocoumarins

Deprotonation of benzocyclobutenols 6 in presence of aromatic aldehydes affords benzopyranols 7 in high yield.In the key step of this process, an o-tolualdehyde anion generated by the known ring-opening of benzocyclobutenoxides adds to the aldehyde to give 7 which is easily oxidized to 3-substituted 3,4-dihydroisocoumarins 8 including intermediates in some natural product syntheses.For example, reaction of 6-methoxybenzocyclobutenol (1) with LTMP and p-anisaldehyde gave in 96percent yield to benzopyranol 16, which subsequently was converted to (+/-)-hydrangenol (17).Similar treatment of 1 with LDA and isovanillin benzyl ether afforded the benzopyranol 19 (87percent yield) which already has been converted to (+/-)-phyllodulcin (21).Finally, reaction of 5,6-(methylenedioxy)benzocyclobutenol (10) with LTMP and the aldehyde 26 (from treatment of hydrastinine with ClCO2Me) followed by methanolysis produced the acetal 28 in 96percent yield.The overall yield was 65percent for the five-step synthesis of the alkaloid (+/-)-peshawawine (24) from 10 and 26.Extension of the process to aliphatic aldehydes was illustrated by the preparation of 32 from benzocyclobutenol and isobutyraldehyde in 69percent overall yield after oxidation with PCC.

o-Toluate carbanions: Facile synthesis of hydrangenol and phyllodulcin

The carbanion generated from the ester 1c on the reaction with appropriate aromatic aldehydes gives the title compounds which are naturally occuring dihydroisocoumarins of pharmacological interest.