2286-54-6

Usage

Uses

Used in Organic Synthesis:
3,3-Diphenylpropiononitrile is used as a key intermediate in the synthesis of various chemical substances. Its unique structure allows for the formation of a wide range of organic compounds, making it a valuable component in the development of new materials and pharmaceuticals.
Used in Pharmaceutical Research:
3,3-Diphenylpropiononitrile is used as a starting material for the synthesis of potential drug candidates. Its properties and reactivity make it a promising candidate for the development of new therapeutic agents, particularly in the fields of chemistry and pharmaceuticals.
Used in Chemical Research:
3,3-Diphenylpropiononitrile is employed as a model compound in various chemical studies, allowing researchers to explore its properties and potential applications. Its unique structure and reactivity provide insights into the behavior of other diphenylmethane derivatives, contributing to the broader understanding of organic chemistry.

InChI:InChI=1/C15H13N/c16-12-11-15(13-7-3-1-4-8-13)14-9-5-2-6-10-14/h1-10,15H,11H2

Upstream product

• 1885-38-7 cinnamic nitrile 
• 3531-24-6 3,3-diphenylacrylonitrile 
• 7474-19-3 3,3-diphenylpropionamide 
• 1883-32-5 2,2-diphenyl ethanol 
• 75-86-5 2-hydroxy-2-methylpropanenitrile 
• 90-99-3 diphenylchloromethane 
• 75-05-8 acetonitrile 
• 119-61-9 benzophenone 
• 574-45-8 N-(diphenylmethylidene)phenylamine 
• 4360-47-8 cinnamonitrile 
• 28446-70-0 (E/Z)-3-(4-methylphenyl)propenenitrile 
• 71-43-2 benzene 
• 28446-72-2 4-chlorocinnamonitrile 
• 7446-70-0 aluminium trichloride 

Downstream Products

• 66529-16-6 2-(2,2-diphenyl-ethyl)-4,5-dihydro-1H-imidazole 
• 606-83-7 3,3-Diphenylpropionic acid 
• 5586-73-2 3-diphenylpropyl amine 
• 41140-46-9 bis-(3,3-diphenyl-propyl)-amine 
• 7474-19-3 3,3-diphenylpropionamide 
• 4812-80-0 1-cyclohexyl-3,3-diphenylpropan-1-one 
• 149553-59-3 2-(2,2-diphenylethyl)-3-isopropylidene-5,5-dimethyl-1-pyrroline 
• 530-48-3 1,1-Diphenylethylene 
• 119-61-9 benzophenone 
• 3531-24-6 3,3-diphenylacrylonitrile 
• 7476-18-8 3,3-diphenyl-propionic acid ethyl ester 
• 390-64-7 prenylamine 
• 73965-93-2 3,3-diphenyl-propionic acid-(2-amino-ethylamide) 
• 1856-33-3 5-benzhydryl-1H-1,2,3,4-tetrazole 

Relevant academic research and scientific papers

Reactions of 3-arylpropenenitriles with arenes under superelectrophilic activation conditions: Hydroarylation of the carbon-carbon double bond followed by cyclization into 3-arylindanones

Reactions of 3-arylpropenenitriles [ArCH[dbnd]CHCN] with arenes [Ar'H] under the superelectrophilic activation conditions with Br?nsted superacid TfOH (CF3SO3H) or strong Lewis acid AlBr3 result, first, in the formation of products of hydroarylation of the carbon-carbon double bond, 3,3-diarylpropanenitriles [Ar(Ar’)CHCH2CN]. Reactions may go further in TfOH leading to 3-arylindanones, as products of intramolecular aromatic acylation by the electrophilically activated nitrile group. Intermediate cationic species, derived at the protonation of the starting 3-arylpropenenitriles onto the carbon of C[dbnd]C bond and the nitrile nitrogen, have been studied by DFT calculation. A plausible reaction mechanism including the formation of highly reactive dications [(Ar)HC+–CH2C+ = NH] has been proposed. The obtained 3,3-diarylpropanenitriles have been transformed into pharmaceutically valuable 5-(2,2-diarylethyl)-1H-tetrazoles [Ar(Ar’)CHCH2Tetr] and 3-diarylpropylamines [Ar(Ar’)CH(CH2)2NH2] by the reactions with NaN3 and LiAlH4 correspondingly.

Double metal cyanides as heterogeneous Lewis acid catalysts for nitrile synthesis: Via acid-nitrile exchange reactions

A series of transition metal-based double metal cyanides (DMCs) were studied as catalysts for the synthesis of nitriles via acid-nitrile exchange reaction. The best nitrile yields were obtained with Co3[Co(CN6)]2 DMC, which proved to be a versatile, stable, reusable and highly active catalyst, exhibiting an activity comparable to that of homogeneous Lewis acid catalysts.

Cinnamonitrile as a precursor of a bi-centered electrophile in reactions with arenes in triflic acid

The reaction of cinnamonitrile [PhCH = CHCN] with arenes in the superacid TfOH at room temperature for 1 h gave two types of compounds, 3-aryl-3-phenyl propionitriles [Ar(Ph)CHCH2CN] and/or 3-phenylindanones in 28–76% yield. The formation of these two reaction products depends on the nucleophilicity of the arene. In these reactions, carbocations generated upon the protonation of cinnamonitrile in TfOH behave as bi-centered electrophiles possessing reactive centers on the C3 carbon of the double bond and on the C1 carbon of the nitrile group.

Rh-catalyzed 1,4-addition reactions of arylboronic acids accelerated by co-immobilized tertiary amine in silica mesopores

Mesoporous silica-supported Rh complex catalysts were prepared by simple silane-coupling, followed by complexation, and characterized by FT-IR, SEM, Rh K-edge XAFS, and elemental analysis. Local structures of the Rh complexes in each sample were almost similar to those of a nonporous silica-supported diaminorhodium complex. Co-immobilization of a tertiary amine on the same silica surface induced slight changes to the Rh complex structure in the case of the support with smaller pores. The prepared catalysts showed high activity for the 1,4-addition reaction of phenylboronic acids. Co-immobilization of the tertiary amine increased the reaction rate by more than 7-fold, with turnover number of nearly 8500. The catalytic performance achieved with this novel system is with much higher than that reported previously with a nonporous silica-supported catalyst. The mesoporous silica-supported Rh complex-tertiary amine showed a wide substrate scope, including unsaturated ketones and nitriles. This co-immobilized tertiary amine may activate phenylboronic acid to enhance its reactivity in the transmetalation step with Rh-OH species.

Cooperative Palladium/Lewis Acid-Catalyzed Transfer Hydrocyanation of Alkenes and Alkynes Using 1-Methylcyclohexa-2,5-diene-1-carbonitrile

Catalytic transfer hydrocyanation represents a clean and safe alternative to hydrocyanation processes using toxic HCN gas. Such reactions provide access to pharmaceutically important nitrile derivatives starting with alkenes and alkynes. Herein, an efficient and practical cooperative palladium/Lewis acid-catalyzed transfer hydrocyanation of alkenes and alkynes is presented using 1-methylcyclohexa-2,5-diene-1-carbonitrile as a benign and readily available HCN source. A large set of nitrile derivatives (>50 examples) are prepared from both aliphatic and aromatic alkenes with good to excellent anti-Markovnikov selectivity. A range of aliphatic alkenes engage in selective hydrocyanation to provide the corresponding nitriles. The introduced method is useful for chain walking hydrocyanation of internal alkenes to afford terminal nitriles in good regioselectivities. This protocol is also applicable to late-stage modification of bioactive molecules.

Process for the Catalytic Reversible Alkene-Nitrile Interconversion

The present invention refers to processes for catalytic reversible alkene-nitrile interconversion through controllable HCN-free transfer hydrocyanation.

HPLC-based kinetics assay facilitates analysis of systems with multiple reaction products and thermal enzyme denaturation

Glucosinolates are plant secondary metabolites abundant in Brassica vegetables that are substrates for the enzyme myrosinase, a thioglucoside hydrolase. Enzyme-mediated hydrolysis of glucosinolates forms several organic products, including isothiocyanates (ITCs) that have been explored for their beneficial effects in humans. Myrosinase has been shown to be tolerant of non-natural glucosinolates, such as 2,2-diphenylethyl glucosinolate, and can facilitate their conversion to non-natural ITCs, some of which are leads for drug development. An HPLC-based method capable of analyzing this transformation for non-natural systems has been described. This current study describes (1) the Michaelis–Menten characterization of 2,2-diphenyethyl glucosinolate and (2) a parallel evaluation of this analogue and the natural analogue glucotropaeolin to evaluate effects of pH and temperature on rates of hydrolysis and product(s) formed. Methods described in this study provide the ability to simultaneously and independently analyze the kinetics of multiple reaction components. An unintended outcome of this work was the development of a modified Lambert W(x) which includes a parameter to account for the thermal denaturation of enzyme. The results of this study demonstrate that the action of Sinapis alba myrosinase on natural and non-natural glucosinolates is consistent under the explored range of experimental conditions and in relation to previous accounts.

Simple Copper Catalysts for the Aerobic Oxidation of Amines: Selectivity Control by the Counterion

We describe the use of simple copper-salt catalysts in the selective aerobic oxidation of amines to nitriles or imines. These catalysts are marked by their exceptional efficiency, operate at ambient temperature and pressure, and allow the oxidation of amines without expensive ligands or additives. This study highlights the significant role counterions can play in controlling selectivity in catalytic aerobic oxidations.

Deboronative cyanation of potassium alkyltrifluoroborates: Via photoredox catalysis

A photoredox catalytic method was developed for the direct cyanation of alkyltrifluoroborates. This reaction provides a new and useful transformation of the easily available alkyltrifluoroborates. The photocatalytic reaction can tolerate a variety of functional groups with mild reaction conditions. Mechanistic investigations are consistent with the present reaction following a radical pathway.

Nitrile synthesis through catalyzed cascades involving acid-nitrile exchange

Irreversible acid-nitrile exchange reactions using both glutaronitrile and (phenylsulfonyl)acetonitrile may be catalyzed by Lewis acids. Whereas a cyclization towards imides displaces the equilibria in the reaction with dinitriles, a decarboxylation step is involved when using the (phenylsulfonyl)acetonitrile. Georg Thieme Verlag Stuttgart New York.