13141-48-5

Usage

Uses

Used in Pharmaceutical Industry:
2-Cyclohexyl-1H-indole is used as a chemical intermediate for the synthesis of various pharmaceuticals, leveraging its indole core structure to contribute to the development of new drugs.
Used in Agrochemical Industry:
2-Cyclohexyl-1H-indole is used as a building block in the creation of agrochemicals, potentially enhancing crop protection and yield through its incorporation into novel compounds.
Used in Research and Development:
2-Cyclohexyl-1H-indole serves as a valuable research compound for studying the effects of cyclohexyl substitution on indole-based molecules, which can lead to advancements in both medicinal chemistry and materials science.
Used in Chemical Synthesis:
2-Cyclohexyl-1H-indole is used as a reagent in the synthesis of complex organic molecules, where its cyclohexyl group may impart unique properties to the final product, such as improved stability or reactivity.

Upstream product

• 53535-83-4 B-cyclohexyl-9-borabicyclo<3.3.1>nonane 
• 54698-11-2 1-methoxyindole 
• 123-91-1 1,4-dioxane 
• 948-65-2 2-phenyl-indole 
• 615-43-0 2-iodophenylamine 
• 823-76-7 Cyclohexyl methyl ketone 
• 26686-10-2 4,7-dihydro-1H-indole 
• 108-94-1 cyclohexanone 
• 695-12-5 vinylcyclohexane 
• 615-36-1 2-bromoaniline 
• 120-72-9 indole 
• 110-82-7 cyclohexane 
• 931-48-6 2-cyclohexylacetylene 
• 2727-71-1 N-(2-bromophenyl)-2,2,2-trifluoroacetamide 

Downstream Products

• 115692-33-6 3-(2-Cyclohexyl-1H-indol-3-yl)-2-[(Z)-hydroxyimino]-propionic acid ethyl ester 
• 84543-21-5 2-cyclohexyl-1-methoxymethylindole-3-carbaldehyde 
• 84543-31-7 ethyl 2-amino-3-(2-cyclohex-1-enyl-1-methoxymethylindol-3-yl)propenoate 
• 84543-25-9 ethyl 2-azido-3-(2-cyclohexyl-1-methoxymethylindol-3-yl)propenoate 
• 1416576-67-4 C₂₃H₂₇NO₃S 
• 1416576-68-5 C₂₄H₂₇NO₄ 
• 68051-20-7 2-cyclohexyl-1-methyl-1H-indole 
• 26216-92-2 2-cyclohexanylindoline 
• 1397585-87-3 (E)-2-cyclohexyl-3-styryl-1H-indole 
• 938326-31-9 2-cyclohexyl-1H-indole-3-carbonitrile 
• 1234333-44-8 (+)-(S)-2-cyclohexanylindoline 
• 1374408-58-8 (R)-2-cyclohexanylindoline 

Relevant academic research and scientific papers

Nickel-Catalyzed Regioselective Cross-Dehydrogenative Coupling of Inactive C(sp3)-H Bonds with Indole Derivatives

A nickel-catalyzed regiosepecific C2- versus C3-oxidative cross-coupling reaction of indoles with 1,4-dioxane and other inactive C(sp3)-H bonds is described. The divergent synthesis of C(sp3)-C(sp2) bonds was achieved in satisfactory yields with di-tert-butyl peroxide (DTBP) as the oxidant, which provides an efficient strategy for the selective construction of cyclic ethers containing heteroaromatic core structures.

A facile one-pot method to synthesise 2-alkylated indole and 2,2′-bis(indolyl)methane derivatives using ketones as electrophiles and their anion sensing ability

Indole derivatives are of great importance because of their biological activity and application in technology. This study explores the synthesis of 2-alkylated indoles derivatives and 2,2′-bis(indolyl)methanes, and their application in anion sensing. The synthesis of a wide range of 2-alkylated indoles and some 2,2′-bis(indolyl)methanes, which cannot be synthesized by previously reported methods, was for the first time accomplished employing dipole exchange of the indole ring towards electrophilic substitution. Some of the indole derivatives exhibited selective recognition and sensing ability towards F- and HSO4- anions through naked-eye detectable color changes. The sensing details of the indole derivatives were also evaluated using UV-Vis spectroscopy and 1H NMR titration techniques.

Inverting Conventional Chemoselectivity in the Sonogashira Coupling Reaction of Polyhalogenated Aryl Triflates with TMS-Arylalkynes

A newly developed phosphine ligand with a C2-cyclohexyl group on the indole ring was successfully applied in a chemoselective Sonogashira coupling reaction with excellent chemoselectivity, affording an inversion of the conventional chemoselectivity order of C–Br > C–Cl > C–OTf. This study also provided an efficient approach to the synthesis of polycyclic aromatic hydrocarbons (PAHs) and the natural product analogue trimethyl-selaginellin L by merging of chemoselective Sonogashira and Suzuki–Miyaura coupling reactions.

Phosphine ligand 2 - alkyl - indole skeleton as well as preparation method and application thereof

The invention discloses a phosphine ligand 2 - alkyl - indole skeleton and a preparation method and application thereof, wherein the structural formula of the phosphine ligand 2 - alkyl - indole skeleton is shown I. , Wherein R. 1 . R2/su

Modular counter-Fischer?indole synthesis through radical-enolate coupling

A single-electron transfer mediated modular indole formation reaction from a 2-iodoaniline derivative and a ketone has been developed. This transition-metal-free reaction shows a broad substrate scope and unconventional regioselectivity trends. Moreover, important functional groups for further transformation are tolerated under the reaction conditions. Density functional theory studies reveal that the reaction proceeds by metal coordination, which converts a disfavored 5-endo-trig cyclization to an accessible 7-endo-trig process.

A Divergent Approach to Indoles and Oxazoles from Enamides by Directing-Group-Controlled Cu-Catalyzed Intramolecular C-H Amination and Alkoxylation

A directing-group-controlled, copper-catalyzed divergent approach to indoles and oxazoles from enamides has been developed. The picolinamide-derived enamides undergo the intramolecular aromatic C-H amination in the presence of a Cu(OPiv)2 catalyst and an MnO2 oxidant to form the corresponding indoles in good yields. On the other hand, simpler aryl- or alkyl-substituted enamides are converted to the 2,4,5-trisubstituted oxazole frameworks via vinylic C-H alkoxylation under identical conditions. The copper catalysis can provide uniquely divergent access to indole and oxazole heteroaromatic cores of great importance in medicinal and material chemistry.

Palladium-Catalyzed Oxidation-Hydroxylation and Oxidation-Methoxylation of N -Boc Indoles for the Synthesis of 3-Oxoindolines

The palladium-catalyzed oxidation-hydroxylation and oxidation-methoxylation of N -Boc indoles for the synthesis of tert -butyl 2-hydroxy(methoxy)-3-oxoindoline-1-carboxylates and their derivatives is developed. The process occurs readily using PdCl 2 as the catalyst and acetonitrile as the solvent to afford 3-oxoindolines in moderate to high yields. A mechanism for this Pd-catalyzed oxidation-hydroxylation and oxidation-methoxylation of N -Boc indoles is proposed.

Iron-Catalyzed Intramolecular C(sp2)-H Amination

The nucleophilic iron complex Bu4N[Fe(CO)3(NO)] (TBA[Fe]) catalyzes the direct intramolecular C-H amination of α-azidobiaryls and (azidoaryl)alkenes into the corresponding carbazoles and indoles, respectively, under mild conditions and with low catalyst loadings. These features and the broad functional-group tolerance render this method a particularly attractive alternative to established noble-metal-based procedures.

One-pot and regiospecific synthesis of 2,3-disubstituted indoles from 2-bromoanilides via consecutive palladium-catalyzed sonogashira coupling, amidopalladation, and reductive elimination

A practical one-pot and regiospecific three-component process for the synthesis of 2,3-disubstituted indoles from 2-bromoanilides was developed via consecutive palladium-catalyzed Sonogashira coupling, amidopalladation, and reductive elimination.

Toward highly potent cancer agents by modulating the C-2 group of the arylthioindole class of tubulin polymerization inhibitors

New arylthioindole derivatives having different cyclic substituents at position 2 of the indole were synthesized as anticancer agents. Several compounds inhibited tubulin polymerization at submicromolar concentration and inhibited cell growth at low nanomolar concentrations. Compounds 18 and 57 were superior to the previously synthesized 5. Compound 18 was exceptionally potent as an inhibitor of cell growth: it showed IC50 = 1.0 nM in MCF-7 cells, and it was uniformly active in the whole panel of cancer cells and superior to colchicine and combretastatin A-4. Compounds 18, 20, 55, and 57 were notably more potent than vinorelbine, vinblastine, and paclitaxel in the NCI/ADR-RES and Messa/Dx5 cell lines, which overexpress P-glycoprotein. Compounds 18 and 57 showed initial vascular disrupting effects in a tumor model of liver rhabdomyosarcomas at 15 mg/kg intravenous dosage. Derivative 18 showed water solubility and higher metabolic stability than 5 in human liver microsomes.