66223-76-5

Upstream product

• 57-57-8 β-Propiolactone 
• 62-53-3 aniline 
• 34535-98-3 D,L-cis-phenylcyclopropylamine 
• 107-21-1 ethylene glycol 
• 102-07-8 bis(diphenyl)urea 
• 1213268-55-3 (E)-4'-hydroxymethylacetophenone oxime 

Downstream Products

• 2210-24-4 N-acryloylaniline 
• 5099-95-6 1-phenylazetidin-2-one 
• 31121-11-6 3-hydroxy-N-phenylpropylamine 

Relevant academic research and scientific papers

CATALYST FOR CONVERTING ESTER TO AMIDE USING HYDROXYL GROUP AS ORIENTATION GROUP

Provided is a method for amidating a hydroxy ester compound at a high chemical selectivity. The amidation reaction method for a hydroxy ester compound comprises, in the presence of a catalyst containing a compound of a transition metal of the group 4 or group 5 in the periodic table, reacting at least one kind of hydroxy ester compound selected from the group consisting of an α-hydroxy ester compound, a β-hydroxy ester compound, a γ-hydroxy ester compound and a δ-hydroxy ester compound with an amino compound so as to amidate an ester group having a hydroxyl group at the α-, β-, γ- or δ-position of the hydroxy ester compound.

Air oxidation of N-cyclopropylanilines

Air oxidation of N-cyclopropylanilines was shown to occur under either ambient conditions or accelerated conditions (warming or shining light) in an open container. A subsequent fragmentation resulted in formation of the corresponding acetamide. While potential mechanisms have been previously proposed, simple aerobic oxidation to β-hydroxy-propionamides in the absence of a radical promoter has not been previously reported. Copyright Taylor & Francis Group, LLC.

Efficient and regioselective synthesis of 5-hydroxy-2-isoxazolines: Versatile synthons for isoxazoles, β-lactams, and γ-amino alcohols

"Chemical Equation Presented" An efficient and highly regioselective protocol was developed for the preparation of 5-hydroxy2-isoxazolines, which have been proved to be versatile synthons for isoxazles, β-hydroxy oximes, and γ-amino alcohols. β-Lactams, commonly embedded in the skeletons of bioactive natural products, were also synthesized in two steps from β-hydroxy oximes, providing a new strategy for the synthesis of this kind of compounds.

Medium Effects on the Rate of Interaction between N,N′-Diphenylurea and Alcohols

The kinetics and mechanism of alcoholysis of symmetrical diphenylurea in inert solvents was studied. The reaction rate was found to be independent of the nature and concentration of the alcohol, which was evidence of the dissociative character of interactions. The reaction involved the decomposition of urea followed by the interaction of the decomposition product (phenylisocyanate) with alcohols. The activation and transition state parameters that characterized the alcoholysis of diphenylurea in various media were found. The influence of the nature of the solvent on the rate of the reaction under consideration was studied.

Autocatalytic radical ring opening of N-cyclopropyl-N-phenylamines under aerobic conditions - Exclusive formation of the unknown oxygen adducts, N-(1,2-dioxolan-3-yl)-N-phenylamines

In contrast to the high stability of N-alkyl-N-cyclopropylamine derivatives, N-cyclopropyl-N-phenylamine (1a) has been found to slowly convert into the hitherto unknown product N-(1,2-dioxolan-3-yl)-N-phenylamine (1f) at room temperature under aerobic conditions. The rate of this conversion was found to be significantly increased by the presence of a catalytic amount of the single-electron oxidizing agent tris(1,10-phenanthroline)FeIII hexafluorophosphate or of the hydrogen-abstracting agents benzoyl peroxide or tertbutyl peroxide/UV light. Based on the regio- and stereochemical outcomes of aerobic ring-opening reactions of some specifically ring-methylated derivatives of 1a, namely N-(1methylcyclopropyl)-N-phenylamine (2a), N-(trans-2-methylcyclopropyl)-N-phenylamine (3a), and N-(cis-2-methylcyclopropyl)-N-phenylamine (4a), as well as other experimental evidence, an autocatalytic mechanism analogous to that of the oxygenation of vinylcyclopropanes is proposed for the formation of the 1,2-dioxolane product. The oxidative radical ring opening and related chemistry of these novel derivatives could be valuable in mechanistic studies of heteroatom-oxidizing enzymes.

Syntheses d'amidoesters par reaction de Kolbe

The synthesis of amidoesters has been investigated by anodic cooxidation of diacid hemiesters CO2H-CH2-Z-CO2CH3 -CH2-> and amidoacids R1-N(Y)-(CH2)2-CO2H .The scope of this reaction was examined in detail.This synthetic pathway provided very a simple access to a wide range of amidoesters R1-N(Y)-(CH2)3-Z-CO2CH3 by varying Z and R1 as well as n value.