39262-02-7

Usage

Uses

Used in Organic Synthesis:
(2E)-3,4-dihydronaphthalene-1,2-dione 2-oxime is used as a building block for the synthesis of various organic compounds, contributing to the development of new chemical entities with potential applications in different industries.
Used in Medicinal Chemistry:
(2E)-3,4-dihydronaphthalene-1,2-dione 2-oxime is utilized as a ligand in coordination chemistry, which is essential for the design and synthesis of metal complexes with potential therapeutic properties.
Used in Research:
(2E)-3,4-dihydronaphthalene-1,2-dione 2-oxime is the subject of ongoing research for its potential biological activity and therapeutic applications, as it may possess properties that can be harnessed for the development of new drugs and treatments.

Upstream product

• 529-34-0 3,4-dihydronaphthalene-1(2H)-one 
• 110-46-3 isopentyl nitrite 

Downstream Products

• 51908-28-2 2-(β-cyanoethyl)benzoic acid 
• 41772-23-0 1-hydroxy-2-naphthylamine hydrochloride 
• 6298-95-9 2-amino-1,2,3,4-tetrahydronaphthalen-1-one hydrochloride 
• 645-59-0 dihydrocinnamonitrile 
• 501-52-0 3-Phenylpropionic acid 
• 904316-34-3 C₁₅H₂₁NO₃ 
• 60505-03-5 2-amino-1,2,3,4-tetrahydronaphthalen-1-one 

Relevant academic research and scientific papers

Enolate-Based Regioselective Anti-Beckmann C-C Bond Cleavage of Ketones

The Baeyer-Villiger or Beckmann rearrangements are established methods for the cleavage of ketone derivatives under acidic conditions, proceeding for unsymmetrical precursors selectively at the more substituted site. However, the fragmentation regioselectivity cannot be switched and fragmentation at the less-substituted terminus is so far not possible. We report here that the reaction of ketone enolates with commercial alkyl nitrites provides a direct and regioselective way of fragmenting ketones into esters and oximes or ω-hydroxyimino esters, respectively. A comprehensive study of the scope of this reaction with respect to ketone classes and alkyl nitrites is presented. Control over the site of cleavage is gained through regioselective enolate formation by various bases. Oxidation of kinetic enolates of unsymmetrical ketones leads to the otherwise unavailable "anti-Beckmann"cleavage at the less-substituted side chain, while cleavage of thermodynamic enolates of the same ketones represents an alternative to the Baeyer-Villiger oxidation or the Beckmann rearrangement under basic conditions. The method is suited for the transformation of natural products and enables access to orthogonally reactive dicarbonyl compounds.