5631-75-4

Upstream product

• 1469-94-9 1-(2-hydroxyphenyl)-3-phenyl-1,3-propanedione 
• 64-17-5 ethanol 
• 46117-36-6 but-3-enoic acid phenyl ester 
• 5751-48-4 2-methylchromone 

Downstream Products

• 129410-09-9 2,3-dihydro-2-methyl-4H-1-benzopyran-4-one 2,4-dinitrophenylhydrazone 
• 5751-48-4 2-methylchromone 
• 62756-35-8 2,3-dihydro-2-methyl-2-phenyl-4H-1-benzopyran-4-one 

Relevant academic research and scientific papers

A Borane-Catalyzed Metal-Free Hydrosilylation of Chromones and Flavones

A Piers-type hydrosilylation of chromones and flavones has been successfully realized for the first time using 0.1 mol % of borane catalyst generated in situ by hydroboration of pentafluorostyrene with HB(C 6 F 5) 2 to afford a variety of chromanones and flavanones in 60-99% yields. An attempt for the asymmetric transformation with chiral diyne and HB(C 6 F 5) 2 gave chromanones and flavanones in high yields with up to 32% ee.

Gold-catalyzed intramolecular hydroarylation of olefins. Scope evaluation and preliminary mechanistic studies

We report a gold-catalyzed intramolecular hydroarylation of unactivated olefins using a combination of AuCl3/AgOTf as the catalytic system affording dihydrobenzopyrans, tetralins and tetrahydroquinolines in good yields. For our preliminary mechanistic studies, we have investigated the kinetic isotope effects with deuterated arene compounds and found that this catalytic hydroarylation is consistent with an electrophilic aromatic substitution process.

3-Hydroxy-(4H)-benzopyran-4-ones as potential iron chelating agents in vivo

Increasing evidence suggests that iron plays an important role in tissue damage both during chronic iron overload diseases (i.e., hemochromatosis) and when, in the absence of actual tissue iron overload, iron is delocalised from specific carriers or intracellular sites (inflammation, eurodegenerative diseases, post-ischaemic reperfusion, etc.). In order to be used for therapeutical purposes in vivo, a reliable iron chelator should be capable of preventing the undesired effects that follow the electrochemical activation of iron (see below). Bearing in mind the molecular structure of some flavonols that are able to chelate iron, we synthesised a new oral iron-chelator, 2-methyl-3-hydroxy-4H-benzopyran-4-one (MCOH). We demonstrate that MCOH chelates iron in a 2:1 ratio showing a stability constant of ～1010. MCOH is able to cross cell membranes (erythrocytes, ascite tumour cells) in both directions. Following intraperitoneal administratio to rats, it is quickly taken up by the liver and excreted in the urine withi 24 h. A similar behaviour has bee documented after oral administration. We propose that MCOH may represent the prototype of a new class of iron chelating agents to be developed for iron-removal therapy in vivo with the goal of preventing tissue damage caused by the iron redox cycle. Copyright

Photolysis of 3-bromochroman-4-ones

Photolysis of 3-bromochroman-4-ones (1a-f) leads to debrominated chromanones (2a-f) and chromones (3a-f) as major products. Their formation is accounted for in terms of primary cleavage of the carbon halogen bond to give α-carbonyl radicals (I) and/or cations (II). In the case of the 2,2-disubstituted compounds (1d-f), intermediates (II) undergo rearrangement with 1,2-shift of the phenyl or benzyl substituent prior to deprotonation. Minor by-products are the pentacyclic pyrone (4e) or 2-methylchromone (3a) (starting from 1e and 1f, respectively).

Cobalt schiff base complex promoted retro-claisen reaction of 1-(2-hydroxyphenyl)-3-phenyl-1,3-propanediones and flavone formation

Co(salpr) promotes the conversion of 1-(2-hydroxyphenyl)-3-phenyl-1,3-propanediones to retro-Claisen reaction products and flavones in methanol under oxygen. Base catalysis by Co(salpr)(OH) produced in situ is responsible for the reaction.