4091-14-9

Usage

InChI:InChI=1/C10H11NO/c1-3-11(9(2)12)10-7-5-4-6-8-10/h3-8H,1H2,2H3

Upstream product

• 13534-87-7 N-(2-acetoxyethyl)acetanilide 
• 103-84-4 Acetanilid 
• 74-86-2 acetylene 
• 593-60-2 Vinyl bromide 

Downstream Products

• 1180843-97-3 C₁₆H₁₅NO 
• 58668-64-7 β--acrolein 
• 1429936-74-2 (E)-N-phenyl-N-(2-(4-(trifluoromethyl)phenylsulfonyl)vinyl)acetamide 
• 1440570-72-8 (E)-ethyl 2,2-difluoro-4-(N-phenylacetamido)but-3-enoate 
• 1440570-60-4 (E)-diethyl 2-[2-(N-phenylacetamido)vinyl]malonate 
• 134919-19-0 N-((E)-4,4-Dicyano-3,3-bis-trifluoromethyl-but-1-enyl)-N-phenyl-acetamide 

Relevant academic research and scientific papers

N-Ethynylation of Anilides Decreases the Double-Bond Character of Amide Bond while Retaining trans-Conformation and Planarity

Activated amide bonds have been attracting intense attention; however, most of the studied moieties have twisted amide character. To add a new strategy to activate amide bonds while maintaining its planarity, we envisioned the introduction of an alkynyl group on the amide nitrogen to disrupt amide resonance by nN→Csp conjugation. In this context, the conformations and properties of N-ethynyl-substituted aromatic amides were investigated by DFT calculations, crystallography, and NMR spectroscopic analysis. In contrast to the cis conformational preference of N-ethyl- and vinyl-substituted acetanilides, N-ethynyl-substituted acetanilide favors the trans conformation in the crystal and in solution. It also has a decreased double bond character of the C(O)?N bond, without twisting of the amide. N-Ethynyl-substituted acetanilides undergo selective C(O)?N bond or N?C(sp) bond cleavage reactions and have potential applications as activated amides for coupling reactions or easily cleavable tethers.

Enamide-benzyne-[2 + 2] cycloaddition: Stereoselective tandem [2 + 2]-pericyclic ring-opening-intramolecular N-tethered [4 + 2] cycloadditions

Image Presented Benzyne-[2 + 2] cycloadditions with enamides are described. This effort led to the development of a highly stereoselective tandem [2 + 2] cycloaddition-pericyclic ring-opening-intramolecular-N-tethered-[4 + 2] cycloaddition for rapid assembly of nitrogen heterocycles.

INVESTIGATION OF THE STRUCTURES OF AND THE INTRAMOLECULAR INTERACTIONS IN N-VINYLAMIDES BY MEANS OF MULTINUCLEAR NMR SPECTROSCOPIC (1H, 13C, 15N, 17O) DATA AND THE RESULTS OF QUANTUM-CHEMICAL CALCULATIONS

As a result of an analysis of the parameters of the 1H, 13C, 15N, and 17O NMR spectra of a number of N-vinylanilides it was established that the phenyl ring is orthogonal to the plane of the amido group, while the vinyl and carbonyl groups are coplanar.Th

SINGLE-STAGE SYNTHESIS OF 3-ARYLAMINO-1-BUTYNES FROM ANILIDES AND ACETYLENE

3-Arylamino-1-butynes were obtained with 20-50percent yields by the reaction of anilides and acetylene (130-160 deg C, initial pressure 12 atm) in the presence of the superbasic system formed during the hydrogenolysis of the anilide by metallic potassium in tetrahydrofuran or dioxane.