33965-80-9

Usage

InChI:InChI=1/C3H4ClNO/c4-1-3(6)2-5/h3,6H,1H2

Upstream product

• 107-20-0 2-chloroethanal 
• 74-90-8 hydrogen cyanide 
• 623-46-1 1,2-dichloro-2-ethoxyethane 
• 151-50-8 potassium cyanide 

Downstream Products

• 7673-65-6 5-methylenehydantoin 
• 74-90-8 hydrogen cyanide 
• 6702-21-2 2-acetoxy-3-chloropropanenitrile 
• 859191-23-4 3-chloro-2-hydroxy-propionimidic acid ethyl ester 

Relevant academic research and scientific papers

Synthesis and reactivity of 5-methylenehydantoins

5-Methylenehydantoin, as well as the N-mono- and N,N-di-protected derivatives, can be obtained by different synthetic routes. These compounds can undergo a large variety of reactions, such as Diels-Alder, epoxidation, methanol addition and conjugate addition reactions of different types of nucleophiles, including carbon (cyanide), nitrogen (piperidine) and sulfur (thiols, thioacetate) nucleophiles. The reactivity with electrophilic reagents, such as m-CPBA or methanol in acidic medium, and the need for Lewis acids to promote the conjugate addition reactions indicate that hydantoin is a poor electron-withdrawing group.

Chiral solvating agents for cyanohydrins and carboxylic acids

We have shown that a structure as simple as an ion pair of (R)- or (S)-mandelate and dimethylamminopyridinium ions possesses structural features that are sufficient for NMR enantiodiscrimination of cyanohydrins. Moreover, 1H NMR data of cyanohydrins of known configuration obtained in the presence of the mandelate-dimethylaminopyridinium ion pair point to the existence of a correlation between chemical shifts and absolute configuration of cyanohydrins. Mandelate-DMAPH+ ion pair and mandelonitrile form a 1:1 complex with an association constant of 338 M-1 (ΔG 0, -3.4 kcal/mol) for the (R)-mandelonitrile/(R)-mandelate-DMAPH + and 139 M-1 (ΔG0, -2.9 kcal/mol) for the (R)-mandelonitrile/(S)-mandelate-DMAPH+ complex. To understand the origin of enantiodiscrimination, the geometry optimization and energy minimization of the models of ternary complexes of (S)-mandelonitrile/(R)- mandelate/DMAPH+ and (S)-mandelonitrile/(S)-mandelate/DMAPH + complexes was performed using DFT methodology (B3LYP) with the 6-31+G(d) basis set in Gaussian 3.0. Further, analysis of optimized molecular model obtained from theoretical studies suggested that (i) DMAP may be replaced with other amines, (ii) the hydroxyl group of mandelic acid is not necessary for stabilization of ternary complex and may be replaced with other groups such as methyl, (iii) the ion pair should form a stable ternary complex with any hydrogen-bond donor, provided its OH bond is sufficiently polarized, and (iv) α-H of racemic mandelic acid should also get resolved with optically pure mandelonitrile. These inferences were experimentally verified, which not only validated the proposed model but also led to development of a new chiral solvating agent for determination of ee of carboxylic acids and absolute configuration of aryl but not alkyl carboxylic acids.

Nitrile hydratase and a method for producing amides

An objective of the present invention is to provide a nitrile hydratase capable of producing 2-hydroxy-4-methylthiobutyroamide. The present invention provides a novel nitrile hydratase producing α-hydroxyamide using, α-hydroxnitrile as the substrate, and the encoding DNA thereof. The enzyme can be obtained from Rhodococcus sp. Further, the enzymatic activity of the enzyme can he maintained stably during the reaction. The present invention provides a method for producing amide compounds, the method comprising the step of reacting this enzyme to nitrile compounds. According to the present invention, from hydroxy nitrile compounds, corresponding amide compounds can be produced biochemically without reducing the enzyme activity of nitrile hydratase.