108706-25-8

Basic information

• Product Name: 3-benzoyl-2,6-dimethyl-4H-1-benzopyran-4-one
• CAS NO: 108706-25-8
• Molecular Weight: 278.307
• Mol File: 108706-25-8.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: 3-benzoyl-2,6-dimethyl-4H-1-benzopyran-4-one(CAS DataBase Reference)
• NIST Chemistry Reference: 3-benzoyl-2,6-dimethyl-4H-1-benzopyran-4-one(108706-25-8)
• EPA Substance Registry System: 3-benzoyl-2,6-dimethyl-4H-1-benzopyran-4-one(108706-25-8)

Safety Data

• Hazardous Substances Data: 108706-25-8(Hazardous Substances Data)

Upstream product

• 16108-51-3 2,6-dimethyl-chromen-4-one 
• 93-89-0 benzoic acid ethyl ester 
• 1450-72-2 5-methyl-2-hydroxyacetophenone 
• 29976-82-7 1-(2-hydroxy-5-methylphenyl)-3-phenylpropane-1,3-dione 
• 108-24-7 acetic anhydride 

Downstream Products

• 256377-80-7 3-Benzoyl-2-((E)-2-dimethylamino-vinyl)-6-methyl-chromen-4-one 

Relevant articles and documents

Benzopyrans. Part 41.1 Reactions of 2-(2-dimethylaminovinyl)-lbenzopyran-4-ones with various dienophiles

Dienamine 1 with W-phenylmaleimide and chromenone 14 as well as 15 produces, through initial [4 + 2]cycloaddition, xanthenones 10 and 18, respectively. Initial Michael addition of 1 to chromenones 14 and 16, and dimethyl acetylenedicarboxylate (DMAD), triggers the formation of xanthenone 19, 4-azaxanthenone 26 and substituted fumarate 49, respectively. Initial [2 + 2]cycloadducts of dienamines 1-3 with electrophilic acetylenes always undergo further transformations. Thus, 1 with DMAD, dibenzoylacetylene and ethyl propiolate (EP) ultimately gives xanthenones 33, 34 and 37, respectively, the latter being admixed with flavone 43. Enamine 2, cyclisable to xanthenone 11, gives 33 and 35 with DMAD, and 37 and 44 with EP. Reaction of 3 with DMAD affords 36 exclusively. The Royal Society of Chemistry 1999.

β-Deprotonation by Lithium Di-isopropylamide. Vinyl Carbanions from Oxygen Heterocycles in the Synthesis of Carboxylic Acids in the Benzofuran, Flavone, and Coumarin Series and in the Regiospecific Acylation of 2,6-Dimethylchromone

Lithium di-isopropylamide at -70 deg C can remove the α-proton from benzofuran in the absence of activating groups and the β-proton if such groups are present; in flavone and 4-methoxycoumarin β-deprotonation occurs readily and the carbanions are easily carboxylated giving acids not previously accessible, while in 2,6-dimethylchromone β-deprotonation is kinetically favoured allowing 3-acylation to be achieved separately from the conventional acylation at the 2-methyl group.