1117218-57-1

Basic information

• Product Name: N-((S)-1-(2-nitrophenyl)ethyl)acetamide
• Synonyms: N-((S)-1-(2-nitrophenyl)ethyl)acetamide
• CAS NO: 1117218-57-1
• Molecular Weight: 208.217
• Mol File: 1117218-57-1.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: N-((S)-1-(2-nitrophenyl)ethyl)acetamide(CAS DataBase Reference)
• NIST Chemistry Reference: N-((S)-1-(2-nitrophenyl)ethyl)acetamide(1117218-57-1)
• EPA Substance Registry System: N-((S)-1-(2-nitrophenyl)ethyl)acetamide(1117218-57-1)

Safety Data

• Hazardous Substances Data: 1117218-57-1(Hazardous Substances Data)

Upstream product

• 198756-82-0 (S)-1-(2-nitrophenyl)ethylamine 
• 108-24-7 acetic anhydride 
• 2354-91-8 (S)-2,2,2-trifluoro-(α-methylbenzyl)acetamide 

Downstream Products

• 1113041-80-7 (S)-1-⁽²⁾-(nitrophenyl)ethylamine hydrochloride 

Relevant articles and documents

Development of robust heterogeneous chiral rhodium catalysts utilizing acid?base and electrostatic interactions for efficient continuous-flow asymmetric hydrogenations

Heterogeneous chiral Rh catalysts based on acid?base and electrostatic interactions have been developed. The robust catalysts demonstrate high activity and selectivity in the continuous-flow asymmetric hydrogenation of a wide variety of enamides and dehyd

Synthesis and Characterization of Nitroaromatic Peptoids: Fine Tuning Peptoid Secondary Structure through Monomer Position and Functionality

N-Substituted glycine oligomers, or peptoids, have emerged as an important class of foldamers for the study of biomolecular interactions and for potential use as therapeutic agents. However, the design of peptoids with well-defined conformations a priori remains a formidable challenge. New approaches are required to address this problem, and the systematic study of the role of individual monomer units in the global peptoid folding process represents one strategy. Here, we report our efforts toward this approach through the design, synthesis, and characterization of peptoids containing nitroaromatic monomer units. This work required the synthesis of a new chiral amine building block, (S)-1-(2-nitrophenyl)ethanamine (s2ne), which could be readily installed into peptoids using standard solid-phase peptoid synthesis techniques. We designed a series of peptoid nonamers that allowed us to probe the effects of this relatively electron-deficient and sterically encumbered a-chiral side chain on peptoid structure, namely, the peptoid threaded loop and helix. Circular dichroism spectroscopy of the peptoids revealed that the nitroaromatic monomer has a significant effect on peptoid secondary structure. Specifically, the threaded loop structure was disrupted in a nonamer containing alternating V-(S)-1-phenylethylglycine (VVspe) and VVs2ne monomers, and the major conformation was helical instead. Indeed, placement of a single Ns2ne at the N-terminal position of (VVspe)9 resulted in a destabilized form of the threaded loop structure relative to the homononamer (VVspe)9. Conversely, we observed that incorporation of V-(S)-1-(4-nitrophenyl)ethylglycine (VVsnp, a p-nitro monomer) at the VV-terminal position stabilized the threaded loop structure relative to (VVspe)9. Additional experiments revealed that nitroaromatic side chains can influence peptoid nonamer folding by modulating the strength of key intramolecular hydrogen bonds in the peptoid threaded loop structure. Steric interactions were also implicated for the VVs2ne monomer. Overall, this study provides further evidence that aromatic side-chain structure, even if perturbed in a single monomer unit, can strongly influence local peptoid backbone conformation.