1646-99-7

Upstream product

• 119-26-6 (2,4-dinitro-phenyl)-hydrazine 
• 1509-34-8 D-allo-isoleucine 
• 319-78-8 D-Isoleucine 
• 1730-97-8 (S)-2-methylbutyraldehyde 
• 1565-80-6 (2S)-2-methyl-1-butanol 
• 96-15-1 2-Methylbutylamine 
• 96-17-3 2-Methylbutyraldehyde 
• 33204-49-8 (R)-2-methyl-butyraldehyde-(2,4-dinitro-phenylhydrazone) 
• 1730-96-7 2,4-dinitrophenylhydrazone of (2S)-2-methyl-1-butanal 

Relevant academic research and scientific papers

Oxidative Degradation of l-Isoleucine by Au3+ Complexes in Weakly Acid Medium: A Kinetic and Mechanistic Investigation

Oxidative degradation of l-isoleucine (Ileu) by Au3+ complexes has been studied spectrophotometrically in weakly acid medium (acetic acid–sodium acetate buffer, pH range 3.72–4.80) in the temperature range 288–308 K. The reaction is first order with respect to AuIII but complex order (+ and Cl? ions have been found to show inhibiting effect on the reaction rate. Decreasing solvent polarity exerts an adverse effect on the reaction. Au3+ complexes react with the zwitterion form of isoleucine in a one-step two-electron transfer redox process. The reaction passes through intermediate formation of iminic cation, which hydrolyzes to produce 2-methyl butanal, identified by 1H NMR. The activation parameters ΔH≠ and ΔS≠ related to the rate-limiting step of the reaction are evaluated. The derived rate law is in excellent agreement with the experimental results. The kinetic and activation parameters of this investigation have been compared and analyzed with those of the oxidation of l-leucine by gold(III).

A modification of a conventional technique for the synthesis of hydrazones of racemic carbonyls: Prevention of spontaneous chiral inversion

Conventionally hydrazones and other derivatives of carbonyls are synthesized under acidic conditions when spontaneous chiral inversion is a common problem if the carbonyl compound is chiral. A new method has been developed involving solid phase microwave-assisted conditions for the synthesis of 2,4-dinitrophenyl hydrazone(s) of chiral carbonyl compounds wherein there occurred no inversion of configuration. The method provided high yields (91-95%) in short reaction times (4-6 min). The method proposed clearly has synthetic advantages over current practices. The hydrazones were characterized by IR, 1H NMR and CHN analysis. The hydrazones represent enantiomeric pairs tagged with a strong chromophore rather than diastereomers. The enantiomeric pairs were separated by HPLC using an α1-acid glycoprotein column and the best resolution of all the analytes was achieved with a mobile phase containing 0.5% 2-propanol in 10 mM citrate phosphate buffer at pH 6.5. The chromatographic peaks clearly showed base line separation with comparable peak areas and thus the results confirmed that there was no spontaneous inversion of configuration during derivatization. The chromatograms corresponding to the products obtained by conventional procedure (from the racemic mixtures of analytes) showed peaks with unequal areas suggesting formation of enantiomers in unequal amounts (i.e., non racemic mixtures) because of spontaneous inversion of the configuration during derivatization.

Oxidation of unactivated primary aliphatic amines catalyzed by an electrogenerated 3,4-azaquinone species: A small-molecule mimic of amine oxidases

High catalytic performance of the electrogenerated amine oxidase mimic 3,4-iminoquinone 1ox is observed under metal-free conditions in the chemoselective oxidation reaction of unactivated primary aliphatic amines.