191930-41-3

Basic information

• Product Name: Phenylalanine, 4-fluoro-, ethyl ester
• CAS NO: 191930-41-3
• Molecular Formula: C11H14FNO2
• Molecular Weight: 211.236
• Mol File: 191930-41-3.mol
• Article Data: 7

Chemical Properties

• CAS DataBase Reference: Phenylalanine, 4-fluoro-, ethyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: Phenylalanine, 4-fluoro-, ethyl ester(191930-41-3)
• EPA Substance Registry System: Phenylalanine, 4-fluoro-, ethyl ester(191930-41-3)

Safety Data

• Hazardous Substances Data: 191930-41-3(Hazardous Substances Data)

Upstream product

• 61924-52-5 ethyl 3-(4-fluorophenyl)-2-nitroprop-2-enoate 
• 32691-93-3 α,α-dimethoxy-4-fluorotoluene 
• 61924-62-7 ethyl 3-(4-fluorophenyl)-2-nitropropanoate 
• 59223-74-4 1,3-diethyl 2-[(4-fluorophenyl)methyl]propanedioate 
• 1353886-54-0 ethyl 3-(4-fluorophenyl)-2-(hydroxyimino)propanoate 
• 64-17-5 ethanol 
• 51-65-0 4-Fluorophenylalanine 
• 459-57-4 4-fluorobenzaldehyde 
• 136265-10-6 ethyl 4-fluorocinnamate 
• 911301-34-3 ethyl 2-azido-3-(4-fluorophenyl)acrylate 

Downstream Products

• 49759-55-9 ethyl N-benzyloxycarbonyl-4-fluorophenylalaninate 

Relevant articles and documents

Synthesis of unnatural α-amino esters using ethyl nitroacetate and condensation or cycloaddition reactions

We report here on the use of ethyl nitroacetate as a glycine template to produce α-amino esters. This started with a study of its condensation with various arylacetals to give ethyl 3-aryl-2-nitroacrylates followed by a reduction (NaBH4 and then zinc/HCl) into α-amino esters. The scope of this method was explored as well as an alternative with arylacylals instead. We also focused on various [2 + 3] cycloadditions, one leading to a spiroacetal, which led to the undesired ethyl 5-(benzamidomethyl)isoxazole-3-carboxylate. The addition of ethyl nitroacetate on a 5-methylene-4,5-dihydrooxazole using cerium(IV) ammonium nitrate was also explored and the synthesis of other oxazole-bearing α-amino esters was achieved using gold(I) chemistry.

Unnatural α-amino ethyl esters from diethyl malonate or ethyl β-bromo-α-hydroxyiminocarboxylate

We have explored here the scope of the age-old diethyl malonate-based accesses to α-amino esters involving Knoevenagel condensations of diethyl malonate on aldehydes, reductions of the resulting alkylidenemalonates, the preparation of the corresponding α-hydroxyimino esters and their final reduction. This synthetic pathway turned out to be general although some unexpected limitations were encountered. The synthetic modifications of some of the intermediates - using Suzuki-Miyaura coupling or cycloadditions - before undertaking the oximation step - provided accesses to further α-amino esters. Moreover, other pathways to α-hydroxyimino esters were explored including an attempt to improve the cycloadditions between ethyl β-bromo-α-hydroxyiminocarboxylate and various alkylfuranes.

Iron-catalyzed oxidative C - H/C - H cross-coupling: An efficient route to α-quaternary α-amino acid derivatives

Fully loaded: A coordinating activation strategy has been developed to furnish α-quaternary α-amino acids through the iron(III)-catalyzed oxidative functionalization of α-C(sp3) - H bonds of α-tertiary α-amino acid esters. The reaction exhibits a broad substrate scope for both α-amino acids and nucleophiles (Nu) as well as good functional-group tolerance (see scheme, DTBP=di-tert-butyl peroxide, DCE=1,2-dichloroethane). Copyright