66185-72-6

Basic information

• Product Name: 2H-1-Benzopyran-2-one, 7-(benzoyloxy)-4-methyl-
• CAS NO: 66185-72-6
• Molecular Formula: C17H12O4
• Molecular Weight: 280.28
• Mol File: 66185-72-6.mol
• Article Data: 10

Chemical Properties

• CAS DataBase Reference: 2H-1-Benzopyran-2-one, 7-(benzoyloxy)-4-methyl-(CAS DataBase Reference)
• NIST Chemistry Reference: 2H-1-Benzopyran-2-one, 7-(benzoyloxy)-4-methyl-(66185-72-6)
• EPA Substance Registry System: 2H-1-Benzopyran-2-one, 7-(benzoyloxy)-4-methyl-(66185-72-6)

Safety Data

• Hazardous Substances Data: 66185-72-6(Hazardous Substances Data)

Upstream product

• 90-33-5 7-hydroxy-4-methyl-chromen-2-one 
• 98-88-4 benzoyl chloride 
• 65-85-0 benzoic acid 
• 93-97-0 benzoic acid anhydride 
• 108-46-3 recorcinol 

Downstream Products

• 68454-14-8 8-benzoyloxy-7-hydroxy-4-methylcoumarin 
• 424807-26-1 (8-benzoyl-4-methyl-2-oxo-2H-chromen-7-yloxy)-acetic acid ethyl ester 
• 113765-91-6 (8-benzoyl-4-methyl-2-oxo-2H-chromen-7-yloxy)-acetic acid 
• 113765-92-7 4-methyl-9-phenylfuro[2,3-h]chromen-2-one 
• 25855-75-8 (2,6-dimethoxyphenyl)(phenyl)methanone 
• 63411-81-4 benzoyl-resorcinol 
• 245728-25-0 8-Benzoyl-7-hydroxy-4-methylcoumarin oxime 
• 20312-83-8 8-Benzoyl-7-hydroxy-4-methylcoumarin 
• 90-33-5 7-hydroxy-4-methyl-chromen-2-one 
• 2555-29-5 8-acetyl-7-hydroxy-4-methyl-2H-chromen-2-one 
• 1140-14-3 2,4-Dimethyl benzophenone 
• 6748-68-1 8-acetyl-7-hydroxycoumarin 
• 90104-85-1 8-Benzoyl-7-hydroxycoumarin 
• 67839-94-5 4-methyl-7-hydroxy-6-benzoylchromen-2-one 

Relevant articles and documents

Synthesis, spectral characterization and α-chymotrypsin activity of 7-O-substituted derivatives of 7-hydroxy-4-methyl-1-benzopyran-2-one

In this work, a series of O-alkyl/arenyl/acyl substituted derivatives of 7-hydorxy-4-methyl-1-benzenpyran-2-one (3a-l) was synthesized. The parent compound 7-hydroxy-4-methyl-1-benzenpyran-2-one (1) was geared up by the coupling of resorcinol (a) with ethylacetoacetate (b) in the presence of conc. sulphuric acid. Further, O-substituted derivatives of parent compound were prepared by treating with different electrophiles (2a-l) using sodium hydride as base and DMF as a solvent. The structure of these synthesized compounds were characterized by IR, EI-MS and 1H NMR. These derivatives were also screened against α-chymotrypsin enzyme to check their enzyme inhibition activity. All the compounds displayed a-chymotrypsin activity to varying degree.

Semisynthesis, ex vivo evaluation, and SAR studies of coumarin derivatives as potential antiasthmatic drugs

Asthma is a chronic inflammatory disorder that causes contraction in the smooth muscle of the airway and blocking of airflow. Reversal the contractile process is a strategy for the search of new drugs that could be used for the treatment of asthma. This work reports the semisynthesis, ex vivo relaxing evaluation and SAR studies of a series of 18 coumarins. The results pointed that the ether derivatives 1-3, 7-9 and 13-15 showed the best activity (E max = 100%), where compound 2 (42 μM) was the most potent, being 4-times more active than theophylline (positive control). The ether homologation (methyl, ethyl and propyl) in position 7 or positions 6 and 7 of coumarins lead to relaxing effect, meanwhile formation of esters generated less active compounds than ethers. The SAR analysis showed that it is necessary the presence of two small ether groups and the methyl group at position 4 (site 3) encourage biological activity through soft hydrophobic changes in the molecule, without drastically affecting the cLogP.

An efficient, mild and scalable synthesis of bioactive compounds containing the angelicin scaffold

An efficient, mild and scalable synthesis of angelicin scaffold based compounds was developed. Particularly, the new synthetic route described here circumvents the need for the previously reported key Fries rearrangement step, which uses impractically har