6963-37-7

Usage

InChI:InChI=1/C9H11NO2/c1-2-9(12)10-7-5-3-4-6-8(7)11/h3-6,11H,2H2,1H3,(H,10,12)

Upstream product

• 64-17-5 ethanol 
• 5260-36-6 2,3-dimethylbenzoxazolium iodide 
• 123-62-6 propionic acid anhydride 
• 95-55-6 2-amino-phenol 
• 18265-75-3 1-(2-hydroxy-phenyl)-propan-1-one oxime 
• 67-64-1 acetone 
• 7732-18-5 water 
• 79-03-8 propionyl chloride 

Downstream Products

• 132283-19-3 Naphthalene-1-carboxylic acid 2-propionylamino-phenyl ester 
• 74251-74-4 Propionsaeure-2-<(E)-2-benzoylvinyloxy>-anilid 

Relevant academic research and scientific papers

Multicatalytic Beckmann rearrangement of 2-hydroxylarylketone oxime: Switchable synthesis of benzo[d]oxazoles and N-(2-hydroxylaryl)amides

A switchable synthesis route is developed for benzo[d]oxazole derivatives and (2-hydroxylaryl)benzamide from 2-hydroxylbenzeneketoxime using organomolecules (BOP-Cl, and CNC) and Lewis acid cocatalyzed Beckmann rearrangement (BR) reaction. Further, this reaction is switched using different organocatalysts.

Carboxyl activation of 2-mercapto-4,6-dimethylpyrimidine through n-acyl-4,6-dimethylpyrimidine-2-thione: A chemical and spectrophotometric investigation

2-Mercapto-4,6-dimethylpyrimidine, as effective carboxyl activating group, has been successfully proved by converting it into respective acyl derivatives and the subsequent conversion to the amides and esters respectively using amines, amino alcohols and alcohols. The aminolysis and esterification were monitored chemically and spectrophotometrically. This paved way to establish that the above mercaptopyrimidine derivative is an efficient carboxyl activating group applicable in solid phase peptide synthesis.

N1,N3-Diacyl-3,4-dihydropyrimidin-2(1H)-ones: neutral acyl group transfer reagents

Readily available N1,N3-diacyl-3,4-dihydropyrimidin-2(1H)-ones efficiently acylate ammonia, primary and secondary amines to furnish primary, secondary and tertiary amides in good to excellent yields. The wide applicability of the procedure is demonstrated

Tertiary Amine-Catalyzed Acyl Group Exchange Reaction of N,O-Diacyl-o-aminophenols. Its Mechanism and Factors Determining the Relative Stability of Acyl Exchanged Isomer Pairs

Acyl substituent effects on the equilibrium and rate constants for the acyl group exchange reactions of various N,O-diacyl-o-aminophenols have been investigated in solvents with different polarities.It was found that the relative stability of acyl exchanged isomer pairs is determined solely by the inductive effect of acyl groups, provided that the steric hindrance of acyl substituents bonded to amide nitrogen affects the stability to the same extent.The importance of steric hindrance exerted by a bulky acyl group in determining the relative stability was demonstrated by analyzing the correlation between the standard free energy change (ΔG0) and pKa, which were used as the measure of the relative stability of isomer pairs and of the electron-with drawing ability of acyl groups, respectively.On the other hand, the logarithms of catalytic rate constants for the acyl migration reactions were correlated well to the pKa values.In addition to this finding, a large negative value of activation entropy (ΔS=-160 J K-1 mol-1) and the Broensted coefficient β of 0.65 for the reaction of N,O-(acetyl)-(1-naphthoyl) pair of N,O-diacyl-o-aminophenol provide a definitive evidence for the rate-determining proton transfer from this derivative to amine catalyst in the transition state.