216753-06-9

Usage

Uses

Used in Organic Synthesis:
(E)-1-(pyridin-2-yl)ethanone O-benzyl oxime is used as a reagent in organic synthesis for its ability to form stable complexes with transition metal ions, which aids in various chemical reactions and the creation of new compounds.
Used in Catalysis:
In the field of catalysis, (E)-1-(pyridin-2-yl)ethanone O-benzyl oxime is used as a catalyst or a catalyst precursor. Its interaction with transition metal ions enhances the efficiency of catalytic reactions, making it a valuable component in this application.
Used in Drug Discovery:
(E)-1-(pyridin-2-yl)ethanone O-benzyl oxime is used as a compound in drug discovery due to its pharmacological properties. It has been investigated for its potential as an antitumor agent, showcasing its importance in the development of new therapeutics for cancer treatment.
Used in Pharmaceutical Industry:
Within the pharmaceutical industry, (E)-1-(pyridin-2-yl)ethanone O-benzyl oxime is utilized as a key intermediate in the synthesis of various drugs, particularly those targeting cancer. Its potential as an antitumor agent and its reactivity make it a promising candidate for the development of novel pharmaceuticals.
Used in Chemical Research:
(E)-1-(pyridin-2-yl)ethanone O-benzyl oxime is also used in chemical research as a model compound to study the interactions between organic molecules and transition metal ions. This research contributes to the understanding of reaction mechanisms and the design of new catalysts and pharmaceuticals.

Upstream product

• 100-39-0 benzyl bromide 
• 79462-42-3 2-[1-(hydroxyimino)ethyl]pyridine 

Relevant academic research and scientific papers

Highly enantioselective borane reduction of heteroaryl and heterocyclic ketoxime ethers catalyzed by novel spiroborate ester derived from diphenylvalinol: Application to the synthesis of nicotine analogues

(Chemical Equation Presented) An asymmetric synthesis for the preparation of nonracemic amines bearing heterocyclic and heteroaromatic rings is described. A variety of important enantiopure thionyl and arylalkyl primary amines were afforded by the borane-mediated enantioselective reduction of O-benzyl ketoximes using 10% of catalyst 10 derived from (S)-diphenylvalinol and ethylene glycol with excellent enantioselectivity, in up to 99% ee. The optimal condition for the first asymmetric reduction of 3- and 4-pyridyl-derived O-benzyl ketoxime ethers was achieved using 30% of catalytic loading in dioxane at 10°C. (S)-N-ethylnornicotine (3) was also successfully synthesized from the TIPS-protected (S)-2-amino-2-pyridylethanol in 97% ee.

CATALYTIC ASYMMETRIC SYNTHESIS OF PRIMARY AMINES VIA BORANE REDUCTION OF OXIME ETHERS USING SPIROBORATE ESTERS

Asymmetric reduction of arylalkyl and pyridylalkyl ketoxime ether with borane catalyzed by several chiral spiroborates derived from non-racemic 1,2-amino alcohols are presented. Complete conversion of oxime to primary amine is highly dependant of the catalyst, source and amount of borane and temperature. The conversion and enantioselectivity is determined by the benzylic substitution of the oxime. After optimization, a catalyst derived from diphenyl valinol could, successfully, afford primary amines with good yield and enantioselectivity up to 99% ee. Using the developed methodology, other related non-racemic primary pyridyl alkyl methanamines were also prepared in high chemical yield and excellent enantioselectivity.