80612-97-1

Basic information

• Product Name: 2-Propenoic acid, 2-amino-3-phenyl-, methyl ester, (2Z)-
• CAS NO: 80612-97-1
• Molecular Formula: C10H11NO2
• Molecular Weight: 177.203
• Mol File: 80612-97-1.mol
• Article Data: 5

Chemical Properties

• CAS DataBase Reference: 2-Propenoic acid, 2-amino-3-phenyl-, methyl ester, (2Z)-(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Propenoic acid, 2-amino-3-phenyl-, methyl ester, (2Z)-(80612-97-1)
• EPA Substance Registry System: 2-Propenoic acid, 2-amino-3-phenyl-, methyl ester, (2Z)-(80612-97-1)

Safety Data

• Hazardous Substances Data: 80612-97-1(Hazardous Substances Data)

Upstream product

• 67-56-1 methanol 
• 74805-42-8 N-carboxy-α-dehydrophenylalanine anhydride 
• 127053-48-9 rac Methyl (2R^*,3S^*)-3-phenyl-1H-aziridine-2-carboxylate 
• 81777-11-9 (Z)-methyl 2-azido-3-phenylacrylate 
• 2577-90-4 methyl (2S)-2-amino-3-phenylpropanoate 
• 72015-61-3 (Z)-2-benzyloxycarbonylaminocinnamic acid 
• 127053-49-0 Methyl (2R^*,3S^*)-2-amino-3-phenyl-3-(phenylthio)propanoate 

Downstream Products

• 6362-58-9 methyl phenylpyruvate 

Relevant articles and documents

Synthesis and preliminary biological evaluation of new phenolic and catecholic dehydroamino acid derivatives

A library of N-phenolic and N-catecholic dehydroamino acid derivatives was prepared using an innovative synthetic strategy that involves mild reaction conditions and simple work-up procedures. The method comprises coupling of phenolic or catecholic acids with β-hydroxyamino acids followed by tert-butyloxycarbonylation of all hydroxyl groups using tert-butyldicarbonate and 4-dimethylaminopyridine as catalyst. Treatment of these amino acids with N,N,N′,N′-tetramethylguanidine affords the corresponding O-tert-butyloxycarbonyldehydroamino acid derivative. Deprotection of the aromatic hydroxyl groups is carried out with trifluoroacetic acid. This synthetic strategy can be applied in a one-pot procedure and yields compounds that can be easily inserted into peptides or other biomolecules after cleavage of the C-protecting group. Preliminary studies of cell viability show that these new compounds display very low or no toxicity. These dehydroamino acids with a phenolic or catecholic moiety can have intrinsic biological activity or used to prepare new hydrogels that mimic mussel adhesive proteins.

Cu/Mn Co-oxidized cyclization for the synthesis of highly substituted pyrrole derivatives from amino acid esters: A strategy for the biomimetic syntheses of lycogarubin c and chromopyrrolic acid

An effective and concise approach to synthesis of tetrasubstituted pyrroles from readily available amino acid esters by the promotion of Cu(OAc) 2 in conjunction with Mn(OAc)3 has been developed. This reaction proceeds through multiple dehydrogenations, deamination, and oxidative cyclization. This oxidized system tolerates substrates bearing various electron-donating or electron-withdrawing groups. With this methodology, several key intermediates of natural products have been effectively prepared, and the total syntheses of lycogarubin C and chromopyrrolic acid have been completed in high efficiency.

Dehydrooligopeptides. V. Synthesis of N-carboxy α-dehydroamino acid anhydrides and their transformation of α-dehydroamino acid and dehydrooligopeptide derivatives

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