63405-13-0

Usage

Chemical structure

A bicyclic heterocyclic compound consisting of a six-membered benzene ring fused to a five-membered nitrogen-containing pyrrole ring, with a cyclohexyl group attached to the first carbon of the indole ring.

Usage

Commonly used in organic synthesis and pharmaceutical research as a building block for the preparation of various bioactive molecules and pharmaceuticals.

Biological activities

Exhibits a diverse range of biological activities, including antiviral, antibacterial, antifungal, and anticancer properties.

Importance

An important chemical intermediate in the production of various drugs, agricultural chemicals, and dyes.

Upstream product

• 120-72-9 indole 
• 4545-18-0 N'-cyclohexylidene-4-methylbenzene-1-sulfonohydrazide 
• 496-15-1 1-indoline 
• 930-68-7 cyclohexenone 
• 108-95-2 phenol 
• 108-91-8 cyclohexylamine 
• 10468-40-3 cyclohexanone N-cyclohexylimine 
• 108-94-1 cyclohexanone 
• 51072-16-3 1-cyclohexyl-4,5,6,7-tetrahydroindole 

Downstream Products

• 1002320-02-6 1-cyclohexyl-2-(4-methylphenyl)-1H-indole 

Relevant academic research and scientific papers

Hydrogen-Transfer-Mediated N-Arylation of Naphthols Using Indolines as Hydrogen Donors

Using a hydrogen-transfer-mediated activation mode, we report a new catalytic system for the transfer hydrogenation of naphthols. In the presence of the Pd/C catalyst and base, various naphthols reacted with indolines to afford N-aryl-substituted heterocyclic compounds. Indolines were found to act as novel hydrogen donors for naphthols under palladium catalysis. This method features good functional tolerance, operational simplicity, and a readily available catalyst.

Ir-Catalyzed Reversible Acceptorless Dehydrogenation/Hydrogenation of N-Substituted and Unsubstituted Heterocycles Enabled by a Polymer-Cross-Linking Bisphosphine

The polystyrene-cross-linking bisphosphine ligand PS-DPPBz was effective for the Ir-catalyzed reversible acceptorless dehydrogenation/hydrogenation of N-heterocycles. Notably, this protocol is applicable to the dehydrogenation of N-substituted indoline derivatives with various N-substituents with different electronic and steric natures. A reaction pathway involving oxidative addition of an N-adjacent C(sp3)-H bond to a bisphosphine-coordinated Ir(I) center is proposed for the dehydrogenation of N-substituted substrates.

The impact of the nature of amine reactants in the palladium catalyzed conversion of phenol to N-substituted anilines

Anilines and cyclohexylamines are currently produced from fossil feedstocks. Phenol would be an attractive alternative feedstock that can be obtained from renewable resources. We herein clarify the influence of the amine on the course of the amination of phenol using a hydrogen borrowing strategy. Amines can in this case act as a reductant which can be dehydrogenated to initiate the partial hydrogenation of phenol which is required for the reaction to take place. The nature of the amine reactant can have a larger effect than the presence of additional reductants like sodium formate. The results in this report do not only present a method for the amination of phenol without addition of an extra reductant, but also rationalize the reactivity of amines in their reaction with phenol.

Formal aromaticity transfer for palladium-catalyzed coupling between phenols and pyrrolidines/indolines

We herein describe a palladium-catalyzed formal aromaticity transfer coupling reaction between phenols and pyrrolidines or indolines to generate the corresponding N-cyclohexyl pyrroles or indoles. In this transformation, the aromaticity of phenols is formally passed on to the pyrrolidine or indoline units. Substituted phenols thus can serve as latent cyclohexyl equivalents for the fast construction of various N-cyclohexyl pyrroles and indoles.

Copper-catalyzed: N -alkylation of indoles by N -tosylhydrazones

An efficient method for the direct N-alkylation of indoles via copper-catalyzed reductive cross coupling between N-tosylhydrazones and indole reagents has been developed. The reaction was performed in the presence of copper iodide and potassium hydroxide by utilization of tri(p-tolyl)phosphine as a ligand. A wide variety of N-alkylated indoles were obtained in moderate to good yields. The application of the current method to the synthesis of biologically active N-alkylated indole derivatives has also been demonstrated.

A Mild Cu(I)-Catalyzed Oxidative Aromatization of Indolines to Indoles

A novel method for the oxidation of indolines to indoles is described. The method uses a Cu(I) catalyst and an organic percarbonate as the stoichiometric oxidant. The procedure was successfully applied at 0.5 kg scale in the production of a key intermediate in the synthesis of Elbasvir, which is a novel therapy for the treatment of hepatitis C virus infection.

Synthesis of N-Alkylated Indolines and Indoles from Indoline and Aliphatic Ketones

A survey of redox aminations of indoline with aliphatic ketones using bismuth nitrate as catalyst is described. A reaction of an equivalent amount of indoline and aliphatic cyclic and acyclic ketones provides a mixture of excessive alkylated indole derivatives over typically redox isomerization and reductive alkylation pathways while using of the five equivalent of indoline provides N-alkylated indolines as a reductive alkylation product. The desired N-alkyl indoles from the oxidation of N-alkyl indolines were obtained in excellent yields.

Discovery and optimization of a new class of potent and non-chiral indole-3-carboxamide-based renin inhibitors

Selective inhibition of the aspartyl protease renin has gained attraction as an interesting approach to control hypertension and associated cardiovascular risk factors given its unique position in the renin-angiotensin system. Using a combination of high-throughput screening, parallel synthesis, X-ray crystallography and structure-based design, we identified and optimized a novel series of potent and non-chiral indole-3-carboxamides with remarkable potency for renin. The most potent compound 5k displays an IC50 value of 2 nM.

Palladium-catalysed N-annulation routes to indoles: The synthesis of indoles with sterically demanding N-substituents, including demethylasterriquinone A1

Tandem palladium-catalysed aryl and alkenyl C-N bond formation allows the synthesis of a variety of indoles bearing sterically demanding N-substituents, including the natural product demethylasterriquinone A1. The Royal Society of Chemistry.

2-(2-Haloalkenyl)-aryl halides as substrates for palladium-catalysed tandem C-N bond formation: Efficient synthesis of 1-substituted indoles

2-(2-Haloalkenyl)-aryl halides, conveniently prepared in a single step from the corresponding o-halobenzaldehydes, are combined with amines under Pd catalysis to provide 1-substituted indoles. All combinations of Br and Cl leaving groups can be employed,