27421-43-8

Basic information

• Product Name: Ethanone, 1-(1-phenyl-1H-indol-3-yl)-
• CAS NO: 27421-43-8
• Molecular Formula: C16H13NO
• Molecular Weight: 235.285
• Mol File: 27421-43-8.mol

Chemical Properties

• CAS DataBase Reference: Ethanone, 1-(1-phenyl-1H-indol-3-yl)-(CAS DataBase Reference)
• NIST Chemistry Reference: Ethanone, 1-(1-phenyl-1H-indol-3-yl)-(27421-43-8)
• EPA Substance Registry System: Ethanone, 1-(1-phenyl-1H-indol-3-yl)-(27421-43-8)

Safety Data

• Hazardous Substances Data: 27421-43-8(Hazardous Substances Data)

Upstream product

• 703-80-0 3-acetylindole 
• 16096-33-6 1-phenyl-1H-indole 
• 141-78-6 ethyl acetate 
• 120-72-9 indole 
• 108-86-1 bromobenzene 
• 591-50-4 iodobenzene 
• 815-57-6 3-Methyl-2,4-pentanedione 
• 98-80-6 phenylboronic acid 

Relevant articles and documents

Diversification of Indoles via Microwave-assisted Ligand-free Copper-catalyzed N-Arylation

A simple, efficient Cu2O catalyst system under microwave irradiation was developed for N-arylation of various indoles without ligands and additives. Diverse N-heteroarylated indoles were prepared by coupling indoles with various heteroaryl hali

Cascade Reaction for the Synthesis of Carbolines from O-Methylketoximes and Styrenes via Palladium-Catalyzed C–H Activation and Sequential Annulation

A novel cascade reaction has been described for the synthesis of Carbolines via palladium-catalyzed successive C–C/C–N formation from O-methylketoximes and styrenes. The oxime ether auxiliary not only serves as a traceless directing group, but is also partly transformed into the value-added pharmacophore in a two-step, one-pot fashion.

Cascade Access to Carboline Carboxylates from Indolyl Ketoximes and Acrylates via Palladium-Catalyzed C-H Bond Alkenylation/Annulation

An efficient palladium-catalyzed C-H bond alkenylation/annulation strategy to access carboline carboxylates from indolyl ketoximes and acrylates through C-C/C-N bond formation is reported. Indolyl ketoximes not only direct ortho -olefination with acrylate

Rhodium(III)-catalyzed C4-amidation of indole-oximes with dioxazolones: Via C-H activation

A novel method for the Rh(III)-catalyzed oxime-directed C-H amidation of indoles with dioxazolones has been developed. This strategy provides an exclusive site selectivity and the directing group can be easily removed. This transformation features a wide substrate scope, good functional group tolerance and excellent yields, and may serve as a significant tool to construct structurally diverse indole derivatives for the screening of potential pharmaceuticals in the future. This journal is

Rapid access to 3-acyl indoles using ethyl acetate/triflic acid couple as the acylium donor and Cu(OAc)2catalysed aerial oxidation of indole benzoins

Esters are potential acyl donors but are relatively unexplored for that purpose. A facile installation of acyl groups at the C-3 position of indoles under triflic acid catalysed conditions with easily available and cheap esters as new acylating agents is described herein. Furthermore, heterocycles like N-protected pyrrole, furan and thiophene were also suitable substrates for similar C-2 acylation. Analogous C-3 benzoylated products of indole were obtained, albeit in lower yields, by using methyl benzoate as a benzoyl donor. The benzoylated products were synthesised in much better yields via a copper(ii) catalysed aerial oxidation of indole containing benzoins. This journal is

Scope, Kinetics, and Mechanism of “On Water” Cu Catalysis in the C–N Cross-Coupling Reactions of Indole Derivatives

A simple and cost-effective protocol for the C–N cross coupling of indole derivatives with aryl iodides using CuI/phenanthroline catalytic system in aqueous and DME/H2O solvent mixture is described. The reactions were performed in the absence of phase-transfer catalyst, and afforded N-arylated products in moderate to excellent yields under mild reaction conditions. A systematic tuning of reaction conditions using DME as a co-solvent enables to improve product yields of N-arylation reactions. The broad substrate scope, easy performance, and low loading of catalyst as well as ligand render this approach appropriate for large scale processes. The mechanism of “on water” Cu-catalyzed N-arylation reaction is investigated using kinetic and computational studies, which reveal interesting mechanistic aspects of the reaction. A series of kinetic experiments showed significant rate enhancement for “on water” Cu-catalyzed N-arylation over the reaction performed in the organic solvent (DME). Computational studies corroborated “on water” rate acceleration by delineating the role of water in the reaction. The water induces rate acceleration by stabilizing the transition state of oxidative addition through hydrogen bonding interactions, presumably at the oil-water interface, and thus helps to reduce the free energy of activation of oxidative addition of iodobenzene to the Cu complex, which is identified as the rate-limiting step of reaction.

Selective C-H acylation of indoles with α-oxocarboxylic acids at the C4 position by palladium catalysis

The first Pd-catalyzed direct C-H acylation of indoles at the C4 position with α-oxocarboxylic acids using a ketone directing group is described. This reaction exhibits high regioselectivity with the tolerance of a wide scope of functional groups to afford diverse acylated indoles in moderate-to-good yields. The control experiments evidence the generation of acyl radicals via K2S2O8 promoted decarboxylation of α-oxocarboxylic acids and the involvement of a PdII/PdIV catalytic cycle. Importantly, the synthetically useful selectivity observed might be applied to prepare indole derivatives with anti-tumor activity as tubulin inhibitors.

Rhodium(III)-Catalyzed Regioselective Direct C4-Alkylation and C2-Annulation of Indoles: Straightforward Access to Indolopyridone

A straightforward RhIII-catalyzed strategy was developed for the site-selective C4-alkylation and C2-annulation of indole by using electronically variable diazo esters. The transformation was accomplished with the assist of an oxime directing group at the C3 position of the indole core with wide scope and functional-group tolerance. The method directly provided an indolopyridone core. The selectivity was triggered by the reactivity of the diazo coupling partner.

Regiocontrolled direct C4 and C2-methyl thiolation of indoles under rhodium-catalyzed mild conditions

A straightforward Rh(iii)-catalyzed general strategy was developed for the site-selective remote C4 (sp2) and C2 (sp3)-methyl thiolation of an indole core, keeping the oxime directing group at the C3 position. The transformation was accomplished under mild conditions with a wide scope and functional group tolerance. The directing group can easily be removed after operation. Methyl substitution at the C2 position of the indole core led to C2 (sp3)-methyl thiolation.

A carbon nitride supported copper nanoparticle composite: a heterogeneous catalyst for the N-arylation of hetero-aromatic compounds

A graphitic carbon nitride supported copper nanoparticle composite (Cu-gCN) has been found to be an active catalyst for the N-arylation of hetero-aromatic systems (pyrrole, pyrazole, and substituted indole) and benzamide molecules, with high product selectivity and good to excellent yields, using substituted aryl bromide as a coupling partner. The intercalated structure and the amine functional group of the carbon nitride prevent the aggregation of the catalytically active copper species during the reaction, and the recyclability study shows the stable performance of the catalyst without a significant loss of catalytic activity.