28319-04-2

Basic information

• Product Name: N-ethyl-N-phenylmethacrylamide
• Synonyms: N-ethyl-N-phenylmethacrylamide
• CAS NO: 28319-04-2
• Molecular Weight: 189.257
• Mol File: 28319-04-2.mol

Chemical Properties

• CAS DataBase Reference: N-ethyl-N-phenylmethacrylamide(CAS DataBase Reference)
• NIST Chemistry Reference: N-ethyl-N-phenylmethacrylamide(28319-04-2)
• EPA Substance Registry System: N-ethyl-N-phenylmethacrylamide(28319-04-2)

Safety Data

• Hazardous Substances Data: 28319-04-2(Hazardous Substances Data)

Upstream product

• 56-23-5 tetrachloromethane 
• 294642-59-4 α-bromo-isobutyric acid-(N-ethyl-anilide) 
• 139-02-6 sodium phenoxide 
• 103-69-5 N-ethyl-N-phenylamine 
• 920-46-7 Methacryloyl chloride 
• 1611-83-2 2-methyl-N-phenylacrylamide 
• 75-03-6 ethyl iodide 

Downstream Products

• 1588429-85-9 1-ethyl-3-methyl-3-((phenylsulfonyl)methyl)indolin-2-one 
• 1638143-34-6 3-(4-nitrobenzyl)-1-ethyl-3-methylindolin-2-one 

Relevant articles and documents

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The synthesis, structure and catalytic activity of a benzene-bridged divanadium complex were comprehensively studied. The reduction of (Nacnac)VCl2(1) (Nacnac = (2,6-iPr2C6H3NCMe)2HC) supported by β-diketiminate with potassium graphite (KC8) by employing benzene as the solvent allows access to the benzene-bridged inverted-sandwich divanadium complex (μ-η6:η6-C6H6)[V(Nacnac)]2(2a), which can catalyze alkene alkylarylation with hypervalent iodine(iii) reagents (HIRs)viadecarboxylation to generate regioselectively diverse indolinones. Furthermore, the mild nature of this reaction was amenable to a wide range of functionalities on alkenes and HIRs. Mechanistic studies revealed a relay sequence of decarboxylative radical alkylation/radical arylation/oxidative re-aromatization.

Synthesis of Dichlorocyanomethyl-Functionalized Oxindoles by Cascade Reactions Initiated by Copper(I)-Catalytically Generated Dichlorocyanomethyl Radical

An efficient and convenient protocol for synthesis of dichlorocyanomethyl-functionalized oxindoles through the cascade reactions of dichlorocyanomethyl radical with N-arylacrylamides is reported. The electrophilic dichlorocyanomethyl radical, which is gen

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Hydroxyl-containing compounds are highly value-Added organic molecules, and the establishment of novel methodologies for their elaboration is a long-standing challenge in organic synthesis. Here the first oxone-mediated direct arylhydroxylation of activat

Catalyst-free and selective trifluoromethylative cyclization of acryloanilides using PhICF3Cl

Trifluoromethylation-triggered cyclization of alkenes provides a useful route to CF3-containing cyclic compounds. Current approaches to generate CF3-based initiators from a CF3 source require a catalyst or an activator. This work describes a catalyst-free protocol to innately produce electrophilic CF3 species from PhICF3Cl for trifluoromethylative cyclization of acryloanilides. A new domino biscyclization of dienes has been developed leading to trifluoroethylated tetrahydroindenoquinolinones with chemo- and stereo-selectivity.

Photocatalytic C-C Bond Activation of Oxime Ester for Acyl Radical Generation and Application

A unified strategy to generate acyl radical from oxime ester via selective C-C bond activation is reported. Under visible-light irradiation, single-electron transfer from fac-Ir(ppy)3 to related oxime takes place followed by a fast β-fragment of C-C bond to yield aryl and aliphatic acyl radicals, subsequently captured by diverse Michael acceptors. More interestingly, the single-electron transfer enables coupling with energy transfer of the excited fac-Ir(ppy)3 via enone intermediate formed in situ for cyclobutane formation.

Dehydrogenative Silylation of Alkenes for the Synthesis of Substituted Allylsilanes by Photoredox, Hydrogen-Atom Transfer, and Cobalt Catalysis

A synergistic catalytic method combining photoredox catalysis, hydrogen-atom transfer, and proton-reduction catalysis for the dehydrogenative silylation of alkenes was developed. With this approach, a highly concise route to substituted allylsilanes has been achieved under very mild reaction conditions without using oxidants. This transformation features good to excellent yields, operational simplicity, and high atom economy. Based on control experiments, a possible reaction mechanism is proposed.

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Visible light sensitization of benzoyl azides was examined in reaction with N-phenylmethacrylamides to afford biologically important oxindoles and spirooxindoles via a cascade cyclization under mild reaction conditions. Mechanistic studies suggested a non-nitrene pathway, where triplet benzoyl azides act as the reactive intermediate.

Light-induced BiOBr nanosheets accelerated highly regioselective intermolecular trifluoromethylation/arylation of alkenes to synthesize CF3-containing aza-heterocycles

A light-induced, BiOBr nanosheets accelerated intermolecular one-pot tandem trifluoromethylation/arylation of alkenes was presented. With this method, a series of CF3-containing aza-heterocycles with high selectivity were fabricated in moderate to good yields. Preliminary mechanistic studies revealed that the exceptional transformation was originated from the synergistic effect of photogenerated electrons and holes. Density function theory (DFT) was adopted to understand the high selectivity of this photocatalytic chemical transformation.

Visible-Light Photoredox Catalysis: Direct Synthesis of Sulfonated Oxindoles from N-Arylacrylamides and Arylsulfinic Acids by Means of a Cascade C-S/C-C Formation Process

A novel photocatalytic synthesis of sulfonated oxindoles from N-arylacrylamides and arylsulfinic acids was developed by means of a cascade C-S/C-C bond-formation process. This method provides mild, efficient, and atom-economical access to various sulfonated oxindoles in water. Let there be light! A novel photocatalytic synthesis of sulfonated oxindoles from N-arylacrylamides and arylsulfinic acids was developed by means of a cascade C-S/C-C bond-formation process. This method provides mild, efficient, and atom-economical access to various sulfonated oxindoles in water (see scheme).

Iron-catalyzed aerobic difunctionalization of alkenes: A highly efficient approach to construct oxindoles by C-S and C-C bond formation

A novel iron-catalyzed efficient approach to construct sulfone-containing oxindoles, which play important roles in the structural library design and drug discovery, has been developed. The use of readily available benzenesulfinic acids, an inexpensive iron salt as the catalyst, and air as the oxidant makes this sulfur incorporation protocol very efficient and practical. This journal is the Partner Organisations 2014.