59483-79-3

Usage

Chemical Structure

The compound features a benzene ring with a cyano (CN) group attached.
Attached to the benzene ring is a 2-oxoethyl group ( \text-COCH2\text- ).
A 4-methylphenyl group ( \text-C6\textH4\text-CH3 ) is also present.

Functional Groups

Cyano group (CN)
2-oxoethyl group ( \text-COCH2\text- )
Methyl group ( \text-CH3 )

Applications

Widely used in organic and medicinal chemistry.
Serves as a crucial building block for synthesizing various pharmaceuticals and biologically active compounds.

Chemical Properties

Aromaticity: Due to the presence of a benzene ring.
Electrophilicity: The cyano group ( \textCN ) can act as an electrophile in reactions.
Reactivity: Reacts readily in organic synthesis due to the presence of functional groups.

Biological Activity

Can be tailored for specific biological activities due to its versatile structure.
Potential for designing new molecules with desired pharmacological properties.

Solubility

Solubility in various solvents can vary depending on the specific chemical environment.

Synthetic Utility

Offers synthetic versatility in creating complex molecules.
Can undergo a variety of chemical transformations to yield diverse products.

Commercial Availability

Available commercially for research and industrial purposes.
Often purchased by pharmaceutical and biotech companies for drug development efforts.

Upstream product

• 104-85-8 para-methylbenzonitrile 
• 62044-37-5 4-cyanophenylacetic acid chloride 
• 108-88-3 toluene 
• 106-38-7 para-bromotoluene 
• 101-82-6 2-Benzylpyridine 
• 5462-71-5 4-cyanophenylacetic acid 

Relevant academic research and scientific papers

Preparation method of aryl ketone compound

The invention provides a preparation method of an aryl ketone compound, and belongs to the technical field of compound synthesis. The method comprises the following steps: under the action of a silver catalyst and water, carrying out reaction on aryl alkyne with a structure as shown in a formula 1 in a solvent at 60-120 DEG C for 12-48 hours, and separating and purifying a product after the reaction is finished, so as to obtain the single aryl ketone compound with a structure as shown in a formula I, the raw materials are easy to obtain, the experimental operation is simple, the yield of the prepared single aryl ketone compound is good, and gram-scale experiments can be carried out.

Tautomer-selective derivatives of enolate, ketone and enaminone by addition reaction of picolyl-type anions with nitriles

We describe an efficient for the synthesis of compounds of tautomeric β-pyridyl/quinolyl-enol, -ketone, -enaminone, which were finally characterized by standard methods like NMR, IR or SCXRD. The addition reaction of lithiated intermediates of picoline, 2-ethylpyridine and 2-methylquinoline, respectively, with nitriles followed by acid hydrolysis afforded the corresponding tautomeric compounds of enol, ketone and emaminone. Interestingly, treatment of 2-methylpyridine or 2-ethylpyridine with nitriles, respectively, yielded mostly β-pyridyl ketone and enol tautomers without enaminones, while 2-methylquinoline with nitriles gave β-quinolyl ketone and enaminone tautomers without enols. The reaction of 2-benzylpyridine with nitriles was not available under the same conditions.

Reactivity of 2-benzylpyridyl lithium toward benzonitrile derivatives: Addition versus elimination

This work investigated the reactivity of 2-benzylpyridyl lithium (2-Pyr)C(Ph)(R)Li (R = SiMe3, Li1; R = H, Li2) toward benzonitrile derivatives. Based on the different products, the reaction between lithium salts and nitriles might involve in addition, elimination and bimolecular coupling pathways, respectively. Treatment of Li1 with ArCN (Ar = Ph, p-Tolyl, o-Tolyl, p-OMePh) yielded an addition intermediate pyridyl-1-aza-allyl-lithium [{(2-Pyr)C(Ph)C(Ar)N(SiMe3)}Li]2 (1, Ar = Ph) and its corresponding hydrolysis product 2-benzylpyridyl-ketone 2–5, respectively, in which the reaction involved in a 1,3-shift of -SiMe3 group to form a dimeric pyridyl-1-aza-allyl-lithium then followed by acidic hydrolysis. The MeOLi elimination reaction between Li2 and p-MeO(C6H4)CN resulted in formation of 4-(2-benzylpyridyl)benzonitrile 6. The reaction of Li2 with p-Me(C6H4)CN in the presence of TMEDA generated a 1:2 hydrolysis adduct 2-benzylpyridyl-enaminone 7, however, in the absence of TMEDA it afforded a coupling product of bimolecular nitriles, 1-(4-methylphenyl)-2-cyanophenyl-ethanone 8. We speculated the reaction mechanisms in sequence. The crystal structures of 1 and 5–8 were analyzed.

Highly regioselective, sequential, and multiple palladium-catalyzed arylations of vinyl ethers carrying a coordinating auxiliary: An example of a heck triarylation process

This article describes the development of new auxiliary-accelerated Heck multiarylations by intramolecular presentation of the oxidative addition complex. The introduction of a specific, palladium-coordinating dimethylamino group allows for the desired chelation-accelerated and chelation-controlled tri- and diarylation reactions. We report (a) the first example of a Heck triarylation process, (b) highly selective palladium-catalyzed diarylations of alkyl vinyl ethers, and (c) a very rapid two-phase protocol for the microwave-assisted hydrolysis of amino-substituted, arylated vinyl ethers constituting an entry to diarylated ethanals and substituted desoxybenzoins. X-ray structures and product patterns support the suggested substrate-controlled Heck reaction pathway. The catalyst-directing alkyl dimethylamino functionality was rapidly (1-2 min) and efficiently released by microwave hydrolysis after Heck multiarylation reactions. The liberated aromatic carbonyl compounds were thereafter isolated and fully characterized.