380-71-2

Basic information

• Product Name: Propanedioic acid, (acetylamino)[(4-fluorophenyl)methyl]-, diethyl ester
• CAS NO: 380-71-2
• Molecular Formula: C16H20FNO5
• Molecular Weight: 325.337
• Mol File: 380-71-2.mol

Chemical Properties

• CAS DataBase Reference: Propanedioic acid, (acetylamino)[(4-fluorophenyl)methyl]-, diethyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: Propanedioic acid, (acetylamino)[(4-fluorophenyl)methyl]-, diethyl ester(380-71-2)
• EPA Substance Registry System: Propanedioic acid, (acetylamino)[(4-fluorophenyl)methyl]-, diethyl ester(380-71-2)

Safety Data

• Hazardous Substances Data: 380-71-2(Hazardous Substances Data)

Upstream product

• 13433-00-6 diethyl aminomalonate hydrochloride 
• 105-53-3 diethyl malonate 
• 502-00-1 p-fluorobenzyl acetate 
• 1068-90-2 2-acetylaminomalonic acid diethyl ester 
• 459-46-1 4-Fluorobenzyl bromide 

Downstream Products

• 453-83-8 N-acetyl-4-fluoro-L-phenylalanine-(N'-phenyl-hydrazide) 
• 69216-82-6 (R)-N-acetyl-p-fluorophenylalanine 
• 18125-46-7 (R)-4-fluorophenylalanine 
• 17481-06-0 rac-Ac-p-F-Phe-OH 
• 51-65-0 4-Fluorophenylalanine 

Relevant articles and documents

Organocatalytic Enantioselective Addition of α-Aminoalkyl Radicals to Isoquinolines

With a dual organocatalytic system involving a chiral phosphoric acid and a dicyanopyrazine-derived chromophore (DPZ) photosensitizer and under the irradiation with visible light, an enantioselective Minisci-type addition of α-amino acid-derived redox-active esters (RAEs) to isoquinolines has been developed. A variety of prochiral α-aminoalkyl radicals generated from RAEs were successfully introduced on isoquinolines, providing a range of valuable α-isoquinoline-substituted chiral secondary amines in high yields with good to excellent enantioselectivities.

Use of acetate as a leaving group in palladium-catalyzed nucleophilic substitution of benzylic esters

The palladium complex prepared in situ from [Pd(η3-C3H5)(cod)]BF4 and bidentate phosphine DPPF was a good catalyst for the nucleophilic substitution of benzyl acetate. Significant acceleration of the palladium-catalyzed substitution was observed when an alcohol was employed as a reaction solvent. The palladium catalyst was effective for the benzylation of various stabilized carbanions, amines, and benzenesulfinate with benzylic acetates.

Synthetic and biotransformation studies on prochiral non-proteinogenic amino acids: Diethyl α-acetamido, α-alkylmalonates

Nine diethyl α-acetamido, α-alkylmalonates 3-11 (alkyl=methyl, benzyl, 3-fluorobenzyl, 4-fluorobenzyl, 2,6-difluorobenzyl, 3-trifluoromethylbenzyl, 4-trifluoromethylbenzyi, 2-chlorobenzyl and 3-chlorobenzyl) have been synthesised in three steps starting with diethyl malonate in overall yields of 49-90%. The structures of C-alkylated acetamidomalonates have been established on the basis of their speciral data, the structures of two compounds 9 and 11 are also confirmed on the basis of their X-ray crystallographic studies. Further, the X-ray crystal structure of the chiral monoethyl ester of α-acetamidomalonic acid 1 has been studied. None of our C-alkylated acetamidomalonate has been found to be a substrate for lipase-catalysed enantiodifferentiating deesterification/hydrolysis of the symmetric diester groups.