17372-53-1

Usage

Uses

Used in Pharmaceutical Industry:
6-Methoxycoumarin is used as a starting material for the synthesis of pharmaceuticals due to its diverse biological activities and potential therapeutic applications.
Used in Agrochemical Industry:
6-Methoxycoumarin is used as a starting material in the synthesis of agrochemicals, leveraging its unique chemical structure and biological properties for pest control and crop protection.
Used in Anticancer Applications:
6-Methoxycoumarin is used as a potential anticancer agent, exhibiting anti-inflammatory, antioxidant, and anticancer properties that can contribute to the development of novel cancer treatments.
Used in Research and Development:
6-Methoxycoumarin is utilized in research and development for studying its biological activities and exploring its potential applications in various fields, including medicine, agriculture, and other industries.

InChI:InChI=1/C10H8O3/c1-12-8-3-4-9-7(6-8)2-5-10(11)13-9/h2-6H,1H3

Upstream product

• 672-13-9 2-hydroxy-5-methoxybenzaldehyde 
• 108-24-7 acetic anhydride 
• 114106-34-2 3-(2-Hydroxy-5-methoxy-phenyl)-3-(2-methoxycarbonyl-ethylsulfanyl)-propionic acid methyl ester 
• 62536-85-0 2-acetoxy-5-methoxybenzaldehyde 
• 16139-79-0 ethyl diphenylphosphonoacetate 
• 150-76-5 4-methoxy-phenol 
• 471-25-0 Propiolic acid 
• 6093-68-1 6-hydroxycoumarin 
• 77-78-1 dimethyl sulfate 
• 90920-97-1 4-methoxyphenyl propynoate 
• 21204-67-1 methyl (triphenylphosphoranylidene)acetate 
• 5683-31-8 3-(trimethylsilyl)prop-2-ynoic acid 
• 201230-82-2 carbon monoxide 
• 103261-31-0 2-hydroxy-5-methoxystyrene 

Downstream Products

• 22927-97-5 6-methoxy-2,2-dimethyl-2H-chromene 
• 38489-78-0 (E)-2-hydroxy-5-methoxycinnamic acid 
• 225791-33-3 2-hydroxy-5-methoxybenzenepropanoic acid 
• 10538-49-5 3-(2,5-dimethoxyphenyl)propanoic acid 
• 40547-03-3 6-Methoxy-4-phenyl-2H-1-benzopyran-2-one 
• 1462913-93-4 C₁₈H₁₄O₃ 
• 1462914-00-6 C₁₉H₁₆O₄ 
• 1462914-03-9 C₁₉H₁₆O₄ 
• 1462914-07-3 C₁₈H₁₃NO₅ 
• 1462914-09-5 C₁₈H₁₃NO₅ 
• 40546-95-0 3,4-dihydro-6-methoxy-4-phenyl-2H-1-benzopyran-2-one 
• 6468-48-0 6-Methoxy-3-phenyl-coumarin 
• 20920-98-3 6-methoxy-3,4-dihydrocoumarin 

Relevant academic research and scientific papers

A practical one-pot synthesis of coumarins in aqueous sodium bicarbonate via intramolecular Wittig reaction at room temperature

An efficient, simple and relatively inexpensive method for the synthesis of coumarins in aqueous sodium bicarbonate at ambient temperature has been developed. It features an intramolecular Wittig reaction of substituted 2-formylphenyl 2-bromoacetate in saturated aqueous sodium bicarbonate. Its advantages include benign reaction conditions, easy work-up and good overall yield with short reaction time. Various substituted coumarins have been synthesized by utilizing this methodology. This journal is

Amine-catalyzed cascade synthesis of 3,4-diunsubstituted coumarins

We disclose an efficient route to synthesize 3,4-diunsubstituted coumarins through a cascade organocatalytic reaction. The reaction is catalyzed by using of a combination of benzylamine (10 mol-%) and triethylamine (10 mol-%). Various salicylaldehydes were tested, and the corresponding coumarin products were obtained in good to high yields under mild and metal-free reaction conditions. We disclose an efficient route to synthesize 3,4-diunsubstituted coumarins through a cascade organocatalytic reaction. The reaction is catalyzed by using of a combination of benzylamine (10 mol-%) and triethylamine (10 mol-%). Various salicylaldehydes are tested, and the corresponding coumarin products are obtained in good to high yields under mild and metal-free reaction conditions. Copyright

Tandem aldehyde-alkyne-amine coupling/cycloisomerization: A new synthesis of coumarins

Cu-catalyzed A3 coupling of ethoxyacetylene, pyrrolidine and salicylaldehydes led to a concomitant cycloisomerization followed by hydrolysis of the resultant vinyl ether to afford coumarins in a cascade process. The reaction proceeded through exclusive 6-endo-dig cyclization and is compatible with halo and keto groups giving coumarins in good to moderate yields.

Gold(I)-Catalyzed Intramolecular Hydroarylation of Phenol-Derived Propiolates and Certain Related Ethers as a Route to Selectively Functionalized Coumarins and 2 H-Chromenes

Methods are reported for the efficient assembly of a series of phenol-derived propiolates, including the parent system 56, and their Au(I)-catalyzed cyclization (intramolecular hydroarylation) to give the corresponding coumarins (e.g., 1). Simple syntheses of natural products such as ayapin (144) and scoparone (145) have been realized by such means, and the first of these subject to single-crystal X-ray analysis. A related process is described for the conversion of propargyl ethers such as 156 into the isomeric 2H-chromene precocene I (159), a naturally occurring inhibitor of juvenile hormone biosynthesis.

Fe(III)-Catalyzed Decarboxylative C3-Difluoroarylmethylation of Coumarins with α,α-Difluoroarylacetic Acids

A facile Fe(III)-catalyzed oxidative decarboxylative radical coupling reaction of α,α-difluoroarylacetic acids with coumarins has been developed. This transformation, which provides a series of C-3 difluoroarylmethylated coumarins containing various functional groups in moderate-to-good yields, features easily accessible starting materials and operational simplicity.

Visible-light-induced regioselective alkylation of coumarins via decarboxylative coupling with N-hydroxyphthalimide esters

An efficient photocatalytic decarboxylative 3-position alkylation of coumarins by using alkyl N-hydroxyphthalimide esters as alkylation reagents has been developed. A variety of NHP esters derived from aliphatic carboxylic acids (primary, secondary, and tertiary) has been proved to be tolerated for this decarboxylation process, affording a broad scope of 3-alkylated coumarin derivatives in moderate to excellent yields. This protocol was highlighted by its mild conditions, readily available starting materials, operational simplicity, and wide functional group tolerance.

Iron-Catalyzed Regioselective Decarboxylative Alkylation of Coumarins and Chromones with Alkyl Diacyl Peroxides

A facile iron-catalyzed decarboxylative radical coupling of alkyl diacyl peroxides with coumarins or chromones has been developed, affording a highly efficient approach to synthesize a variety of α-alkylated coumarins and β-alkylated chromones. The reaction proceeded smoothly without adding any ligand or additive and provided the corresponding products containing a wide scope of functional groups in moderate to excellent yields. This protocol was highlighted by its high regioselectivity, readily available starting materials, and operational simplicity.

Fabrication of an amyloid fibril-palladium nanocomposite: A sustainable catalyst for C-H activation and the electrooxidation of ethanol

Amyloids are highly ordered nanofibrils and their tensile strength is similar to that of steel, which makes them resistant to extreme pH and temperature. Based on this rationale, we demonstrate a facile synthesis of palladium, copper, platinum, gold and silver nanocomposites using α-Synuclein (α-Syn) fibrils as a template. We showed that an α-Syn-fibril-palladium nanoparticles (α-Syn-PdNPs) composite can be used as a heterogeneous catalyst in C-H bond activation and the electrooxidation of ethanol. The study demonstrated α-Syn-PdNPs to be a superior heterogeneous catalyst for the synthesis of pharmaceutically valuable benzofuran, naphthofuran, coumarin and N-arylindole via C-H activation. Further, the electrooxidation of ethanol using α-Syn-PdNPs displayed an electrochemically active surface area of 160.6 m2 g-1, which is much higher than the previously reported values for supported Pd nanocomposites.

Microwave-Assisted Synthesis of Phenylpropanoids and Coumarins: Total Synthesis of Osthol

Herein we describe a one-pot microwave-assisted method for the synthesis of cinnamic acid and coumarin derivatives. The synthesis begins with an aldehyde synthon, and the chosen reaction conditions determine whether a cinnamic acid or coumarin derivative is formed. A regioselective Claisen rearrangement was also efficiently incorporated into the synthetic sequence to further increase the complexity of the product. Notably, this approach provides high product yields and selectivities without the need of a phenol protecting group.

Metal-free, Br?nsted acid-mediated synthesis of coumarin derivatives from phenols and propiolic acids

A novel synthesis of coumarin derivatives by Br?nsted acid-mediated condensation and intramolecular cyclization of phenols and propiolic acids was reported. This transformation requires the use of TfOH in place of a conventional metal mediator, and it occurs under mild conditions and provides rapid access to coumarin derivatives in good yields.