85094-87-7

Usage

Derivative of indole

Bicyclic heterocyclic organic compound 1H-Indole,2-ethynyl-1-methylis derived from indole, which is a bicyclic (two interconnected rings) heterocyclic (containing at least one non-carbon atom) organic compound.

Ethynyl group

Triple bond between carbon and hydrogen The compound contains an ethynyl group, which is a triple bond (a bond consisting of three shared electron pairs) between a carbon atom and a hydrogen atom.

Methyl group attachment

Carbon atom A methyl group (a group consisting of one carbon atom and three hydrogen atoms) is attached to a carbon atom in the 1H-Indole,2-ethynyl-1-methylcompound.

Application in organic synthesis

Pharmaceutical research 1H-Indole,2-ethynyl-1-methylis used in organic synthesis, which is the study of the synthesis of organic compounds, and in pharmaceutical research for the development of new drugs.

Interest in optoelectronics

Unique chemical structure and properties The compound's unique chemical structure and properties make it of interest in the development of new materials for optoelectronics, which is the study of devices and systems that interact with light.

Potential biological activity

Drug development 1H-Indole,2-ethynyl-1-methylexhibits potential biological activity, meaning it may have an effect on biological systems, and is being studied for its potential use in the development of new drugs.

Upstream product

• 108164-08-5 2,2-dimethyl-5-(1-methylindol-2-ylmethylene)-1,3-dioxane-4,6-dione 
• 603-76-9 1-methylindole 
• 27421-51-8 1-methyl-1H-indole-2-carboxaldehyde 
• 90965-06-3 dimethyl 1-(1-diazo-2-oxopropyl)phosphonate 
• 75833-63-5 2-iodo-1-methyl-1H-indole 
• 85094-83-3 1-(1'-methyl-2'-indolyl)-3-methyl-1-butyn-3-ol 

Downstream Products

• 1192143-12-6 1-(2-((1-methyl-1H-indol-2-yl)ethynyl)phenyl)ethanone 
• 1262153-49-0 C₂₆H₂₅NO₆ 
• 1262153-52-5 C₃₃H₃₀N₂O₆S 
• 1262153-71-8 C₃₀H₂₇NO₄ 
• 128351-01-9 1-methyl-2-(2-phenylethynyl)-1H-indole 
• 1262153-43-4 C₂₄H₂₃NO₄ 
• 1262153-78-5 C₂₂H₂₁NO₂ 
• 1262153-76-3 C₂₄H₂₂⁽²⁾HNO₄ 
• 1262153-48-9 C₂₄H₂₂ClNO₄ 
• 1262153-47-8 C₂₅H₂₅NO₅ 
• 1262153-50-3 C₂₅H₂₂N₂O₄ 
• 1413923-25-7 C₁₉H₁₆N₂O₂ 
• 1413923-26-8 C₁₈H₁₃FN₂O 

Relevant academic research and scientific papers

Iron-Catalyzed Vinylzincation of Terminal Alkynes

Organozinc reagents are among the most commonly used organometallic reagents in modern synthetic chemistry, and multifunctionalized organozinc reagents can be synthesized from structurally simple, readily available ones by means of alkyne carbozincation. However, this method suffers from poor tolerance for terminal alkynes, and transformation of the newly introduced organic groups is difficult, which limits its applications. Herein, we report a method for vinylzincation of terminal alkynes catalyzed by newly developed iron catalysts bearing 1,10-phenanthroline-imine ligands. This method provides efficient access to novel organozinc reagents with a diverse array of structures and functional groups from readily available vinylzinc reagents and terminal alkynes. The method features excellent functional group tolerance (tolerated functional groups include amino, amide, cyano, ester, hydroxyl, sulfonyl, acetal, phosphono, pyridyl), a good substrate scope (suitable terminal alkynes include aryl, alkenyl, and alkyl acetylenes bearing various functional groups), and high chemoselectivity, regioselectivity, and stereoselectivity. The method could significantly improve the synthetic efficiency of various important bioactive molecules, including vitamin A. Mechanistic studies indicate that the new iron-1,10-phenanthroline-imine catalysts developed in this study have an extremely crowded reaction pocket, which promotes efficient transfer of the vinyl group to the alkynes, disfavors substitution reactions between the zinc reagent and the terminal C–H bond of the alkynes, and prevents the further reactions of the products. Our findings show that iron catalysts can be superior to other metal catalysts in terms of activity, chemoselectivity, regioselectivity, and stereoselectivity when suitable ligands are used.

In situ generation of the Ohira-Bestmann reagent from stable sulfonyl azide: Scalable synthesis of alkynes from aldehydes

We report an improved method for in situ generation of the Ohira-Bestmann reagent. Using the recently reported bench-stable imidazole-1-sulfonyl azide as diazotransfer reagent, this new method represents a scalable and convenient approach for the transformation of aldehydes into terminal alkynes. The method features an easier workup compared to the existing in situ protocol due to increased aqueous solubility of waste products.

Tandem cyclopropane ring-opening/conia-ene reactions of 2-alkynyl indoles: A [3 + 3] annulative route to tetrahydrocarbazoles

A Zn(NTf2)2 catalyzed tandem reaction consisting of a nucelophilic ring opening of 1,1-cyclopropanediesters by 2-alkynyl indoles followed by a Conia-ene ring closure results in the efficient one-step synthesis of tetrahydrocarbazoles

Flash Vacuum Pyrolysis of 5-(Indol-2- and -3-ylmethylene)-2,2-dimethyl-1,3-dioxane-4,6-diones

Flash vacuum pyrolysis of 5-(indol-2- and -3-ylmethylene)-2,2-dimethyl-1,3-dioxane-4,6-diones results in the initial formation of indolylmethyleneketenes, which generally either lose carbon monoxide to produce ethynylindoles or undergo -sigmatropic shifts, followed by electrocyclic rearrangements, to yield carbazolols or benzindol-5(1H)-one. 5-(Indol-2-ylmethylene)-2,2-dimethyl-1,3-dioxane-4,6-dione and the 3-methylindol-2-yl derivative both yield 3H-pyrroloindol-3-ones via a -sigmatropic rearrangement of the initially formed ketene.