100717-32-6

Basic information

• Product Name: 3-Cyclohexyl-1H-indole
• Synonyms: 3-cyclohexyl-1H-Indole
• CAS NO: 100717-32-6
• Molecular Formula: C₁₄H₁₇N
• Molecular Weight: 199.29
• Mol File: 100717-32-6.mol

Chemical Properties

• Boiling Point: 366.8 °C at 760 mmHg
• Flash Point: 160.7 °C
• Appearance: /
• Density: 1.088
• Vapor Pressure: 3.02E-05mmHg at 25°C
• Refractive Index: 1.62
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• CAS DataBase Reference: 3-Cyclohexyl-1H-indole(CAS DataBase Reference)
• NIST Chemistry Reference: 3-Cyclohexyl-1H-indole(100717-32-6)
• EPA Substance Registry System: 3-Cyclohexyl-1H-indole(100717-32-6)

Safety Data

• Hazardous Substances Data: 100717-32-6(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
3-Cyclohexyl-1H-indole is used as a key intermediate in the synthesis of various pharmaceuticals for its potential analgesic, anti-inflammatory, and anti-cancer properties. Its unique structure allows it to interact with biological targets, offering therapeutic benefits in pain management, reducing inflammation, and combating cancer cells.
Used in Agrochemical Industry:
In the agrochemical sector, 3-Cyclohexyl-1H-indole is utilized as a precursor in the development of compounds with pesticidal or herbicidal activities. Its chemical structure can be modified to target specific pests or weeds, contributing to more effective and selective crop protection agents.
Used in Research and Development:
3-Cyclohexyl-1H-indole serves as a valuable compound in scientific research, particularly in the fields of medicinal chemistry and drug discovery. It is used to explore new chemical entities and investigate their mechanisms of action, potentially leading to the development of novel therapeutic agents.

InChI:InChI=1/C14H17N/c1-2-6-11(7-3-1)13-10-15-14-9-5-4-8-12(13)14/h4-5,8-11,15H,1-3,6-7H2

Upstream product

• 120-72-9 indole 
• 108-93-0 cyclohexanol 
• 1027208-32-7 3-cyclohexyl-2-ethylsulfanyl-1H-indole 
• 64126-56-3 1-(Indol-3-yl)-cyclohexen 
• 110-83-8 cyclohexene 
• 79202-15-6 diethyl (hydroxy)(2-nitrophenyl)methylphosphonate 
• 552-89-6 2-nitro-benzaldehyde 
• 108-94-1 cyclohexanone 
• 1262588-92-0 3-cyclohexyl-2-(triethylsilyl)-1H-indole 
• 931-48-6 2-cyclohexylacetylene 
• 148991-61-1 triethylsilyl(cyclohexylethynyl)silane 
• 1431934-77-8 1,2-bis(2-cyclohexylideneethyl)-1,2-bis(2-iodophenyl)hydrazine 
• 496-15-1 1-indoline 
• 15121-84-3 2-nitro-benzeneethanol 

Downstream Products

• 1262588-67-9 3-cyclohexyl-2-(3-methoxyphenyl)-1-methylindole 
• 172983-86-7 3-cyclohexyl-1-methyl-1H-indole 
• 1311205-18-1 C₁₆H₁₈F₃N 
• 1428236-58-1 C₂₅H₂₇NO₃ 
• 1504-16-1 3-phenyl-1H-indole 
• 92250-13-0 3-cyclohexylindolin-2-one 

Relevant articles and documents

Highly diastereoselective oxa-[3+3] cyclization with C,N-cyclic azomethine imines: Via the copper-catalyzed aerobic oxygenated CC bond of indoles

Herein, a copper-catalyzed highly diastereoselective aerobic oxygenated [3+3] cyclization of 3-substituted indoles with C,N-cyclic azomethine imines using oxygen as the sole oxidant under mild conditions has been developed. This protocol provides a simple and convenient approach for constructing [2,3]-fused indoline O-heterocycles bearing two pharmaceutically intriguing parts, tetrahydroisoquinoline and indoline. Good yields and excellent diastereoselectivity under mild reaction conditions were observed.

Palladium-catalyzed intermolecular alkenylation of indoles by solvent-controlled regioselective C-H functionalization

(Chemical Equation Presented) Either the C2- or the C3-substituted product can be obtained with the same palladium(II) catalyst in an oxidative intermolecular alkenylation of indoles. A variety of conditions can be used for derivatization at the 3-positio

Annulative π-Extension (APEX) of Indoles to Pyrido[1,2- a]indoles Using 4-Oxo Peroxides as C4 Units

Annulative π-extension (APEX) of 3-substituted indoles to pyrido[1,2-a]indoles is developed by using 4-oxo peroxides as π-extending reagents, which are employed as versatile C4 building blocks. This transformation is initiated by Br?nsted acid-mediated Hock rearrangement of the peroxyl group. Notably, the pyrido[1,2-a]indole products are obtained by elimination of the indole moiety from the corresponding dihydropyrido[1,2-a]indoles, which could be selectively formed at room temperature.

Aerobic C-H olefination of indoles via a cross-dehydrogenative coupling in continuous flow

Herein, we report the first site-selective, Pd(II)-catalyzed, cross-dehydrogenative Heck reaction of indoles in micro flow. By use of a capillary microreactor, we were able to boost the intrinsic kinetics to accelerate former hour-scale reaction condition

Transition-Metal-Catalyzed Regioselective Alkylation of Indoles with Alcohols

The regioselective alkylation of indoles with alcohols as alkylating reagents was developed by using Pd/C or RuCl2(PPh3) 3/DPEphos {DPEphos = bis[(2-diphenylphosphanyl)phenyl] ether}as catalysts. The reaction of indole with benzyl alcohol in the presence of Pd/C and K2CO3 at 80 °C for 24 h without any solvent under in air yielded 90 % of 3-benzylindole. The corresponding 3-benzylindole was obtained in 99 % yield when the reaction was catalyzed by RuCl 2(PPh3)3/DPEphos in the presence of K 3PO4 at 165 °C for 24 h under argon. Several types of alcohols were treated with indoles under these conditions to give the corresponding 3-alkylated indoles in high yields (up to 99 %). This reaction may involve the catalyst-mediated transformation of alcohols to aldehydes, nucleophilic addition of indole to the resulting aldehydes accompanied by dehydration, and then hydrogenation. Copyright

Nickel-catalyzed C3-alkylation of indoles with alcohols: Via a borrowing hydrogen strategy

An efficient method for the Ni-catalyzed C3-alkylation of indoles using readily available alcohols as the alkylating reagents has been developed. The alkylation was addressed with an air and moisture-stable binuclear nickel complex ligated by tetrahydroquinolin-8-one as the effective pre-catalyst. The newly developed transformation could accommodate a broad substrate scope including primary/secondary benzylic and aliphatic alcohols and substituted indoles. Mechanistic studies suggested that the reaction proceeds through a borrowing hydrogen pathway.

Ruthenium Pincer Complex Catalyzed Selective Synthesis of C-3 Alkylated Indoles and Bisindolylmethanes Directly from Indoles and Alcohols

Herein, we presented Ru-SNS complex that serves as a useful catalyst for C-3 alkylation of 1H-indoles with various aliphatic primary and secondary alcohols including cyclic alcohols as well as benzylic alcohols. The selective synthesis of bisindolylmethane derivatives is also achieved from the same set of indole and alcohol just by altering the reaction parameters. Furthermore, the sustainable synthesis of C-3 alkylated indoles directly from 2-(2-nitrophenyl)ethan-1-ol and alcohols catalysed by a Ru-complex via “borrowing hydrogen” strategy is reported. This protocol provides an atom-economical sustainable route to access structurally important compounds like arundine, vibrindole A and tryptamine based derivatives. (Figure presented.).

Arylation of indoles using cyclohexanones dually-catalyzed by niobic acid and palladium-on-carbons

3-Arylindoles were easily constructed from indoles and cyclohexanone derivatives using a combination of catalytic niobic acid-on-carbon (Nb2O5/C) and palladium-on-carbon (Pd/C) under heating conditions without any oxidants. The Lewis acidic Nb2O5/C promoted the nucleophilic addition of indoles to the cyclohexanones, and the subsequent dehydration and Pd/C-catalyzed dehydrogenation produced the 3-arylindoles. The additive 2,3-dimethyl-1,3-butadiene worked as a hydrogen acceptor to facilitate the dehydrogenation step.

Preparation method of 3-substituted oxidized indole and derivative

The invention belongs to the technical field of organic chemistry and pharmaceutical chemistry and particularly relates to a method of preparing 3-substituted oxidized indole and a derivative. In themethod, with a 3-substituted indole derivative as a raw material and one or more of a tetrabutyl ammonium halide compound/sodium chloride/sodium iodide/potassium iodide as additives, and one or more of dichloromethane/1,2-dichloroethane/tetrahydrofurane/methylbenzene/1,4-dioxane/ethyl acetate/methanol are added as solvents; then one or more of [bis(trifluoroacetoxyl)iodine]benzene/iodosobenzene diacetate are added as oxidants in order to carry out a reaction with reaction temperature being controlled, thus producing the 3-substituted oxidized indole derivative. The method has gentle reaction conditions, simple operations, short reaction time and high yield, and is free of a metal catalyst and is environment-friendly.

Ether Synthesis through Reductive Cross-Coupling of Ketones with Alcohols Using Me 2 SiHCl as both Reductant and Lewis Acid

We report that a Lewis acidic silane, Me 2 SiHCl, can mediate the direct cross-coupling of a wide range of carbonyl compounds with alcohols to form dialkyl ethers. The reaction is operationally simple, tolerates a range of polar functional groups, can be utilized to make sterically hindered ethers, and is extendable to sulfur and nitrogen nucleophiles.