5280-02-4

Basic information

• Product Name: 1-(benzyloxy)-2(1H)-pyridinone
• Synonyms: 1-(benzyloxy)-2(1H)-pyridinone
• CAS NO: 5280-02-4
• Molecular Formula: C₁₂H₁₁NO₂
• Molecular Weight: 201.22124
• Mol File: 5280-02-4.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 1-(benzyloxy)-2(1H)-pyridinone(CAS DataBase Reference)
• NIST Chemistry Reference: 1-(benzyloxy)-2(1H)-pyridinone(5280-02-4)
• EPA Substance Registry System: 1-(benzyloxy)-2(1H)-pyridinone(5280-02-4)

Safety Data

• Hazardous Substances Data: 5280-02-4(Hazardous Substances Data)

Usage

Chemical Family

Pyridinone family

Molecular Weight

201.2 g/mol

Usage

Synthesis of pharmaceuticals

Potential Medicinal Properties

Studied for its potential medicinal properties

Building Block

Used as a building block in organic synthesis

Biological Activities

Shown promising biological activities in research studies

Structure

Contains a pyridine ring with a substituted benzyl ether group

Versatility

A versatile compound in the field of pharmaceutical chemistry

Valuable Compound

Considered valuable in pharmaceutical chemistry due to its structure and potential applications

Upstream product

• 20773-98-2 2-methoxypyridine N-oxide 
• 100-44-7 benzyl chloride 
• 13161-30-3 2-hydroxy-pyridine N-oxide 
• 100-39-0 benzyl bromide 
• 1254765-78-0 1-((4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzyl)oxy)pyridin-2(1H)-one 
• 5033-19-2 2-oxopyridin-1(2H)-yl benzenesulfonate 
• 1325206-84-5 4-(((2-oxopyridin-1(2H)-yl)oxy)methyl)phenylboronic acid 
• 1259401-64-3 4-(((2-oxopyridin-1(2H)-yl)oxy)sulfonyl)benzoic acid 
• 5087-06-9 2-oxopyridin-1(2H)-yl 4-methylbenzene sulfonate 
• 40864-08-2 2-benzyloxypyridine 
• 2402-95-1 2-chloropyridine-N-oxide 
• 109-09-1 2-chloropyridine 
• 2683-67-2 2-benzyloxypyridine 1-oxide 
• 111302-00-2 2,3-dimethoxypyridine N-oxide 

Downstream Products

• 822-89-9 1-Hydroxy-2-pyridon 
• 142-08-5 2-Pyridone 
• 100-52-7 benzaldehyde 
• 100-51-6 benzyl alcohol 
• 40775-55-1 1-methoxy-2-pyridone 

Relevant articles and documents

STIMULUS-TRIGGERED PRODRUGS

Set forth herein, inter alia, are compositions and methods for treating diseases with prodrugs. Provided herein are prodrug compositions for inhibiting the function of proteins, compositions and methods for treating diseases associated with oxidative compounds, oxidatively-sensitive prodrugs of inhibitors of metalloproteases. and methods of inhibiting metalloproteases using oxidatively-sensitive prodrugs.

A topochemical rearrangement with multiple inversions of configuration

Crystalline 2-benzyloxypyridine-1-oxide rearranges slowly at room temperature to crystalline 1-benzyloxy-2-pyridone. No intermediates are detected when the process is followed by solid-state 13C NMR. The crystal structure of the pyridine-1-oxid

Alkyl transfer with retention and inversion of configuration: Reexamination of a putative [1s,4s] sigmatropic rearrangement

The thermal rearrangement of 2-alkoxypyridine-1-oxides to 1-alkoxy-2-pyridones, which has been reported to proceed by an intramolecular [1s,4s] sigmatropic migration of the alkyl group with retention of configuration and first-order kinetics, has been reexamined. The intramolecular barriers have been computed to be at least 20 kcal mol-1 higher than the reported experimental barriers. An alternative bimolecular mechanism, discovered computationally, has been confirmed by a variety of experiments including crossover studies, determination of solvent effects and secondary H/D isotope effects, and new kinetic and stereochemical studies. In the new mechanism there is an initial intermolecular transfer of the alkyl group, with inversion of configuration, to the N-oxide. Depending on the nature of the alkyl group and the solvent, this is followed by a second transfer, also with inversion of configuration, of one of the alkyl groups of the cationic intermediate to one of the oxygens of the anionic intermediate. The product is then formed either without crossover, by a double inversion of one alkyl group, or with crossover by two single inversions of different alkyl groups. The proposed intermediates of this mechanism can be synthesized; they react to form a 1-alkoxy-2-pyridone at room temperature.

STUDIES ON THE THERMAL REARRANGEMENT OF 2-METHOXYPYRIDINE N-OXIDES TO 1-METHOXYPYRIDIN-2-ONES

A study of the influence of the solvent polarity on the rearrangement of 2-methoxypyridine N-oxides to 1-methoxypyridin-2-ones suggests an ionic mechanism.

APPLICATION OF QUARTERNARY PHOSPHONIUM SALTS IN ALKYLATION AND ACYLATION OF N-HYDROXYLACTAMS

Reactions of N-hydroxylactams with alcohols and carboxylic acids in presence of triphenylphosphine and diethyl azodicarboxylate have been described.Contrary to corresponding acyclic amides (hydroxamic acids), cyclic compounds form under these conditions O