31709-47-4

Basic information

• Product Name: 3-(4-METHOXYPHENYL)-5(4H)-ISOXAZOLONE
• Synonyms: 3-(4-METHOXYPHENYL)-5(4H)-ISOXAZOLONE
• CAS NO: 31709-47-4
• Molecular Formula: C₁₀H₉NO₃
• Molecular Weight: 191.18336
• Mol File: 31709-47-4.mol
• Article Data: 17

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 3-(4-METHOXYPHENYL)-5(4H)-ISOXAZOLONE(CAS DataBase Reference)
• NIST Chemistry Reference: 3-(4-METHOXYPHENYL)-5(4H)-ISOXAZOLONE(31709-47-4)
• EPA Substance Registry System: 3-(4-METHOXYPHENYL)-5(4H)-ISOXAZOLONE(31709-47-4)

Safety Data

• Hazardous Substances Data: 31709-47-4(Hazardous Substances Data)

Usage

General Description

3-(4-Methoxyphenyl)-5(4H)-isoxazolone, also known as mexidol, is a chemical compound that belongs to the class of isoxazolones. It is a drug with neuroprotective and anti-inflammatory properties, and is used for the treatment of various neurological disorders such as stroke, traumatic brain injury, and cognitive impairment. Its mechanism of action involves reducing oxidative stress, increasing the activity of antioxidant enzymes, and enhancing the functioning of cell membranes. It has also been found to have anti-anxiety and antidepressant effects. Mexidol has shown potential for improving cognitive function and memory, making it a promising candidate for the treatment of neurodegenerative diseases.

Upstream product

• 90788-35-5 (Z)-3-amino-3-(4-methoxyphenyl)acrylic acid ethyl ester 
• 616-38-6 carbonic acid dimethyl ester 
• 100-06-1 1-(4-methoxyphenyl)ethanone 
• 22027-50-5 methyl 3-(4-methoxybenzoyl)acetate 
• 123-11-5 4-methoxy-benzaldehyde 
• 33172-00-8 (+/-)-ethyl 3-hydroxy-3-(4-methoxyphenyl)propanoate 
• 104548-24-5 4-acetoxy-3-methoxycarbonyl-4-(4-methoxyphenyl)but-3-ene-2-one 
• 2881-83-6 ethyl 4-methoxybenzoylacetate 
• 124-38-9 carbon dioxide 
• 2475-92-5 4-methoxyacetophenone oxime 

Downstream Products

• 76148-56-6 3,3'-bis(4-methoxyphenyl)-2H,2'H-2,2'-bibenzo[b][1,4]thiazine 
• 52485-97-9 (Z)-4-benzylidene-3-(4-methoxyphenyl)isoxazol-5(4H)-one 
• 35113-43-0 4-benzylidene-3-(4-methoxy-phenyl)-4H-isoxazol-5-one 
• 93041-45-3 3-(4-methoxy)-5-methylisoxazole-4-carboxylic acid 
• 92545-94-3 3-(4-hydroxy-phenyl)-5-methyl-isoxazole-4-carbonyl chloride 
• 92286-62-9 3-(4-hydroxy-phenyl)-5-methyl-isoxazole-4-carboxylic acid 
• 25755-89-9 methyl 3-(4-methoxyphenyl)-2H-azirine-2-carboxylate 

Relevant articles and documents

Palladium Catalyzed Ring Expansion Reaction of Isoxazolones with Isocyanides: Synthesis of 1,3-Oxazin-6-One Derivatives

A palladium catalyzed ring expansion reaction of isoxazolones with isocyanides was disclosed. In the reaction, a cascade process involving ring-opening/cyclization was suggested. The reaction features high atomic economy due to no elimination of CO2 occurred. Moreover, products obtained demonstrate aggregation-induced emission properties with relatively high solid-state emission efficiencies. (Figure presented.).

Suzuki-Miyaura cross-coupling of 3,4-disubstituted 5-bromoisoxazoles: An efficient access to trisubstituted isoxazoles

The Suzuki-Miyaura cross-coupling of 3,4-disubstituted 5-bromoisoxazoles 1 at the C5 position has successfully proceeded in the presence of Pd2(dba)3 and P(t-Bu)3·HBF4 catalysts to give the corresponding trisubstituted isoxazoles 3 in good to high yields while suppressing the formation of ketone 4 as a byproduct. The use of bulky phosphine ligand P(t-Bu)3·HBF4 is essential for the current transformation, and the formation of ketone 4, which was a major product in the previous report, was able to be suppressed under the current conditions.

Cooperative Catalysis with Coupled Chiral Induction in 1,3-Dipolar Cycloadditions of Azomethine Ylides

1,3-Dipolar cycloadditions (1,3-DC) between imino esters (as precursors of N-metallated azomethine ylides) and π-deficient alkenes are promoted by cooperative asymmetric Lewis acid/Br?nsted base catalysis. The components of these catalytic pairs are silver salts derived from enantiopure commercially available BINOL-based phosphoric acids and Cinchona alkaloids. Chiral phosphoric silver(I) salts promote HOMO raising of in situ formed 1,3-dipoles, whereas protonated cinchona alkaloids generate a LUMO lowering for the dipolarophiles resulting in a global acceleration of the 1,3-DC. The best results were obtained with BINOL-derived silver phosphate and hydrocinchonine. Matching between both cooperative metallo- and organocatalyst results in an enhanced enantiomeric excess, superior to that reached by both separate components. NOESY experiments and DFT calculations are compatible with a non-covalent interaction (hydrogen bond) between both catalysts, which results in close contacts and mutually coupled chiral environments.