153864-57-4

Upstream product

• 1603-79-8 phenylglyoxylic acid ethyl ester 
• 100-63-0 phenylhydrazine 
• 52328-57-1 ethyl α-(Z-phenylhydrazono)benzeneacetate 

Downstream Products

• 1603-79-8 phenylglyoxylic acid ethyl ester 
• 52328-57-1 ethyl α-(Z-phenylhydrazono)benzeneacetate 
• 184579-08-6 (Methyl-hydrazono)-phenyl-acetic acid ethyl ester 
• 52328-62-8 C₁₈H₁₈N₂O₄ 

Relevant academic research and scientific papers

Structure Property Analysis of the Solution and Solid-State Properties of Bistable Photochromic Hydrazones

The development of new photochromic compounds and the optimization of their photophysical and switching properties are prerequisites for accessing new functions and opportunities that are not possible with currently available systems. To this end we recen

Photochromic Hydrazone Switches with Extremely Long Thermal Half-Lives

A family of easily accessible light-activated hydrazone switches has been developed having thermal half-lives of up to 2700 years! Structure-property analysis shows that replacing the rotor pyridyl group of our typical hydrazone switch with a phenyl one leads to the long-lived negative photochromic compounds. The switching properties of the hydrazones in both toluene and DMSO were assessed offering insights into the kinetics and thermodynamics of the switching process.

Hydrazone Photoswitches for Structural Modulation of Short Peptides

Molecules that undergo light-driven structural transformations constitute the core components in photoswitchable molecular systems and materials. Among various families of photoswitches, photochromic hydrazones have recently emerged as a novel class of photoswitches with superb properties, such as high photochemical conversion, spectral tunability, thermal stability, and fatigue resistance. Hydrazone photoswitches have been adopted in various adaptive materials at different length scales, however, their utilization for modulating biomolecules still has not been explored. Herein, we present new hydrazone switches that can photomodulate the structures of short peptides. Systematic investigation on a set of hydrazone derivatives revealed that installation of the amide group does not significantly alter the photoswitching behaviors. Importantly, a hydrazone switch comprising an upper phenyl ring and a lower quinolinyl ring was effective for structural control of peptides. We anticipate that this work, as a new milestone in the research of hydrazone switches, will open a new avenue for structural and functional control of biomolecules.

Oxidation of hydrazones by hypervalent organoiodine reagents: Regeneration of the carbonyl group and facile syntheses of α-acetoxy and α-alkoxy azo compounds

Various hydrazone derivatives of α-keto esters were prepared. The carbonyl group was readily regenerated in high yield from phenylhydrazones through oxidative hydrolysis using hypervalent organoiodine(III) reagents either bis(trifluoroacetoxy)-iodobenzene (BTIB) in aqueous acetonitrile or hydroxy(tosyloxy)iodobenzene (HTIB) in chloroform. α-Acotxy phenyl- or methylazo compounds were readily synthesized by oxidation of the corresponding hydrazones with iodobenzene diacetate (IBDA) in dichloromethane or acetic acid. α-Methoxy phenyl- or methylazo compounds were also prepared by oxidation of the hydrazones in methanol. The mechanisms of the oxidation reactions are discussed.