76311-94-9

Basic information

• Product Name: Propanoic acid, 3-oxo-3-(phenylamino)-, methyl ester
• CAS NO: 76311-94-9
• Molecular Formula: C10H11NO3
• Molecular Weight: 193.202
• Mol File: 76311-94-9.mol
• Article Data: 20

Chemical Properties

• CAS DataBase Reference: Propanoic acid, 3-oxo-3-(phenylamino)-, methyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: Propanoic acid, 3-oxo-3-(phenylamino)-, methyl ester(76311-94-9)
• EPA Substance Registry System: Propanoic acid, 3-oxo-3-(phenylamino)-, methyl ester(76311-94-9)

Safety Data

• Hazardous Substances Data: 76311-94-9(Hazardous Substances Data)

Upstream product

• 59-88-1 phenylhydrazine hydrochloride 
• 105-34-0 methyl 2-cyanoacetate 
• 67-56-1 methanol 
• 15580-32-2 malonanilic acid 
• 62-53-3 aniline 
• 108-59-8 malonic acid dimethyl ester 
• 103-71-9 phenyl isocyanate 
• 102-08-9 N,N-diphenylthiourea 
• 37517-81-0 3-chloro-3-oxopropanoic acid methyl ester 
• 124-38-9 carbon dioxide 
• 5326-87-4 N-(phenyl)bromoacetamide 
• 74-88-4 methyl iodide 
• 587-65-5 N-chloroacetyl-aniline 
• 122347-10-8 4,4-Dimethoxy-1-phenyl-2-azetidinone 

Downstream Products

• 80420-99-1 3-Anilino-2-(phenylcarbamoyl)propensaeure-methylester 
• 15775-59-4 N¹-hydroxy-N³-phenylmalonamide 
• 76311-82-5 2,6-Dioxo-1-phenyl-hexahydro-furo[3,4-b]pyrrole-3-carboxylic acid methyl ester 
• 76311-80-3 3-Methyl-5-oxo-1-phenyl-pyrrolidine-2,4-dicarboxylic acid dimethyl ester 
• 76311-77-8 5-Oxo-1-phenyl-pyrrolidine-2,4-dicarboxylic acid 2-ethyl ester 4-methyl ester 
• 14438-90-5 N-phenylpropanediamide 
• 852619-54-6 N-phenyl-N'-(2-tritylsulfanyl-ethyl)-malonamide 
• 15580-32-2 malonanilic acid 

Relevant articles and documents

Phosphonate as a Stable Zinc-Binding Group for “Pathoblocker” Inhibitors of Clostridial Collagenase H (ColH)

Microbial infections are a significant threat to public health, and resistance is on the rise, so new antibiotics with novel modes of action are urgently needed. The extracellular zinc metalloprotease collagenase H (ColH) from Clostridium histolyticum is a virulence factor that catalyses tissue damage, leading to improved host invasion and colonisation. Besides the major role of ColH in pathogenicity, its extracellular localisation makes it a highly attractive target for the development of new antivirulence agents. Previously, we had found that a highly selective and potent thiol prodrug (with a hydrolytically cleavable thiocarbamate unit) provided efficient ColH inhibition. We now report the synthesis and biological evaluation of a range of zinc-binding group (ZBG) variants of this thiol-derived inhibitor, with the mercapto unit being replaced by other zinc ligands. Among these, an analogue with a phosphonate motif as ZBG showed promising activity against ColH, an improved selectivity profile, and significantly higher stability than the thiol reference compound, thus making it an attractive candidate for future drug development.

Iodine-mediated aryl transfer reaction from arylhydrazine hydrochlorides to nitriles

An iodine-promoted, metal-, base-, and solvent-free cross-coupling reaction was developed for the synthesis of various useful secondary amides via an aryl N-addition reaction of aryl groups to cyano groups. This aryl transfer reaction proceeds with arylhydrazine hydrochlorides serving as the aryl donors. A labelling experiment shows that the N atom in the product comes from the cyano group of the nitriles, which are low in cost. A plausible radical-driven mechanism is also proposed.

Hypervalent Iodine(III)-Promoted Phenyl Transfer Reaction from Phenyl Hydrazides to Nitriles

A useful transformation of nitriles to N-phenyl amides has been achieved through a novel intermolecular phenyl transfer reaction from phenyl hydrazides and N-addition to nitriles in the presence of PIFA under mild and solvent-free conditions. This cross-coupling reaction includes the oxidative cleavage of sp2 C-N bonds of phenyl hydrazides to form a phenyl radical and the subsequent N-addition to cyanos to form new sp2 C-N bonds and provides efficient access to various N-phenyl amides in moderate to good yields under mild reaction conditions.