2555-28-4

Usage

Uses

Used in Biochemical Applications:
7-Methoxy-4-methylcoumarin is used as a biochemical marker for the determination of Cytochrome P450 activity. This application is crucial in understanding and studying the metabolic processes involving this essential enzyme family, which plays a vital role in drug metabolism and detoxification in living organisms.
Used in Organic Synthesis:
7-Methoxy-4-methylcoumarin is also utilized as a compound in organic synthesis. Its unique chemical structure makes it a valuable building block for the creation of more complex molecules and compounds, contributing to the advancement of chemical research and development in various industries.

InChI:InChI=1/C11H10O3/c1-7-5-11(12)14-10-6-8(13-2)3-4-9(7)10/h3-6H,1-2H3

Upstream product

• 150-19-6 O-methylresorcine 
• 590-93-2 2-Butynoic acid 
• 141-97-9 ethyl acetoacetate 
• 151-10-0 1,3-Dimethoxybenzene 
• 77067-28-8 3-bromo-4-bromomethyl-7-methoxycoumarin 
• 91-66-7 N,N-diethylaniline 

Downstream Products

• 54283-64-6 3-<2,4-Dimethoxy-phenyl>-trans-crotonsaeure 
• 7706-67-4 3-(2,4-dimethoxy-phenyl)-cis-crotonic acid 
• 66611-99-2 7-methoxy-4-methyl-8-nitrocoumarin 
• 1413412-77-7 C₂₆H₂₀N₂O₅ 
• 1413412-87-9 4-(7-methoxy-4-methyl-2-oxo-2H-chromen-3-yl)benzaldehyde 
• 1413412-81-3 C₃₃H₂₆N₂O₅ 
• 1413412-93-7 5-(7-methoxy-2-oxo-2H-chromen-4-yl)cyclohexane-1,3-dione 
• 1456809-34-9 7-hydroxy-3-((4-hydroxy-3,5-dimethylphenyl)ethynyl)-4-methyl-2H-chromen-2-one 
• 1456809-27-0 (E)-3-(4-hydroxy-3,5-dimethylstyryl)-7-methoxy-4-methyl-2H-chromen-2-one 
• 1456809-41-8 (E)-7-methoxy-3-(4-((2-methoxyethoxy)methoxy)-3,5-dimethylstyryl)-4-methyl-2H-chromen-2-one 
• 1456809-44-1 7-methoxy-3-((4-((2-methoxyethoxy)methoxy)-3,5-dimethylphenyl)ethynyl)-4-methyl-2H-chromen-2-one 
• 1456809-29-2 (E)-7-hydroxy-3-(4-hydroxy-3,5-dimethylstyryl)-4-methyl-2H-chromen-2-one 
• 1456809-32-7 3-((4-hydroxy-3,5-dimethylphenyl)ethynyl)-7-methoxy-4-methyl-2H-chromen-2-one 
• 1594100-97-6 C₁₈H₁₄N₂O₄ 

Relevant academic research and scientific papers

Photochemical release of amines by C,N-bond cleavage

A method for the photorelease of primary and secondary amines using coumarin as chromophore was developed. This mild C,N-bond cleavage reactions liberates the amine not only in solution but also on solid support.

Environmentally friendly synthesis of coumarin derivatives employing heterogeneous catalysis

Zeolite H-BEA and other solid acids have been shown to be effective catalysts for the production of coumarin derivatives from activated phenols and acids or esters possessing an additional alkylation function, or β-keto esters (Pechmann reaction). These heterogeneous catalysts eliminate the production of acidic waste streams associated with conventional (Lewis) acid catalysts. Zeolite H-BEA proved to be the preferred catalyst.

Synthesis of Highly Functionalized Flavones and Chromones Using Cycloacylation Reactions and C-3 Functionalization. A Total Synthesis of Hormothamnione

The cycloacylations of hydroxy- and methoxy-substituted phenols with aryl- and alkylpropiolic acids using Eaton's reagent (10percent phosphorus pentoxide in methanesulfonic acid) gives highly substituted flavones and chromones in up to 63 percent yield.Styrylchromones were prepared from 2-methylchromones by condensation reactions of the 2-methyl group with various substituted benzaldehydes in sodium ethoxide and ethanol in almost quantitative yield.Methylation or hydroxylation at C-3 of these highly substituted flavones and styrylchromones was accomplished in a highly regioselective manner employing lithium diisopropylamide followed by quenching with an electrophile.Quenching of the initial anion with methyl triflate gave 3-methyl products while quenching of the initial anion with trimethylborate followed by oxidation gave 3-hydroxy products.A total synthesis of the naturally occurring styrylchromone hormothamnione, containing a 3-methyl substituent, is reported by use of these synthetic techniques.

SOME REACTIONS OF 3-BROMO-4-BROMOMETHYL-7-METHOXYCOUMARIN AND 3-BROMO-4-METHYL-7-METHOXYCOUMARIN WITH REFLUXING N,N-DIETHYLANILINE.

N,N-diethylaniline effectively debrominated 3-bromo-4-methyl-7-methoxycoumarin and 3-bromo-4-bromomethyl-7-methoxycoumarin, at reflux.This and other reactions of the above-mentioned coumarins in refluxing N,N-diethylaniline provided supporting evidence for the mechanism of the fragmentation of simple 4-aryloxy-2-bromobut-2-enoates which occurred during their attempted Claisen rearrangement in refluxing N,N-diethylaniline.