5840-59-5

Usage

Uses

Used in Organic Synthesis:
(2Z)-2-(4-methoxyphenyl)-3-phenylprop-2-enenitrile is used as a building block in organic synthesis for the creation of various complex organic molecules. Its nitrile and alkene groups facilitate participation in a range of chemical reactions, making it a versatile component in the synthesis of pharmaceuticals, agrochemicals, and other specialty chemicals.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, (2Z)-2-(4-methoxyphenyl)-3-phenylprop-2-enenitrile is used as an intermediate in the development of new drugs. Its aromatic rings and functional groups can be modified to create bioactive molecules with potential therapeutic applications.
Used in Materials Science:
(2Z)-2-(4-methoxyphenyl)-3-phenylprop-2-enenitrile is utilized in materials science for the development of novel materials with specific properties. Its aromatic and functional groups can be incorporated into polymers, coatings, and other materials to enhance their performance characteristics.

Upstream product

• 141-52-6 sodium ethanolate 
• 100-52-7 benzaldehyde 
• 104-47-2 p-methoxybenzylnitrile 
• 100-51-6 benzyl alcohol 

Downstream Products

• 1086-43-7 2-(4-methoxyphenyl)-2,3-dihydro-1H-inden-1-one 
• 1769-85-3 (±)-2-(4-methoxyphenyl)-3-phenylpropanoic acid 
• 39104-22-8 3-Phenyl-2-<4-methoxy-phenyl>-propionsaeure-chlorid 
• 145962-41-0 2-(4-methoxyphenyl)indanamine 
• 145962-42-1 2-(4-methoxyphenyl)-1-indanone oxime methyl ether 
• 7497-45-2 2-(4-methoxyphenyl)-3-phenylsuccinonitrile 
• 5840-58-4 2-(4-methoxyphenyl)-3-phenylpropanenitrile 

Relevant academic research and scientific papers

α-Alkylation of arylacetonitriles with primary alcohols catalyzed by backbone modified N-heterocyclic carbene iridium(i) complexes

A series of backbone-modified N-heterocyclic carbene (NHC) complexes of iridium(i) (1d-f) have been synthesized and characterized. The electronic properties of the NHC ligands have been assessed by comparison of the IR carbonyl stretching frequencies of thein situprepared [IrCl(CO)2(NHC)] complexes in CH2Cl2. These new complexes (1d-f), together with previously prepared1a-c, were applied as catalysts for the α-alkylation of arylacetonitriles with an equimolar amount of primary alcohols or 2-aminobenzyl alcohol. The catalytic activities of these complexes could be controlled by modifying the N-substituents and backbone of the NHC ligands. The NHC-IrIcomplex1fbearing 4-methoxybenzyl substituents on the N-atoms and 4-methoxyphenyl groups at the 4,5-positions of imidazole exhibited the highest catalytic activity in the α-alkylation of arylacetonitriles with primary alcohols. Various α-alkylated nitriles and aminoquinolines were obtained in high yields through a borrowing hydrogen pathway by using 0.1 mol%1fand a catalytic amount of KOH (5 mol%) under an air atmosphere within significantly short reaction times.

Switchable Cobalt-Catalyzed α-Olefination and α-Alkylation of Nitriles with Primary Alcohols

The first switchable α-olefination and α-alkylation of nitriles with primary alcohols catalyzed by a well-defined base transition-metal Co complex was presented. A broad variety of nitriles and primary alcohols are selectively and efficiently converted to the corresponding products by this method. It is noteworthy that the transformation is environmentally benign and atom efficient with H2and H2O being the sole byproducts.

Synthesis of non-symmetrical 3,4-diaryl-substituted pyrroles: Implementation for the preparation of lamellarin R

A straightforward method for synthesising symmetrical and non-symmetrical 3,4-diaryl-substituted pyrroles is proposed, consisting of (i) the condensation reaction between phenylacetonitriles and aldehydes to give acrylonitriles, (ii) the conjugate additio

Application of group v polyoxometalate as an efficient base catalyst: A case study of decaniobate clusters

The base catalytic activity of the decaniobate cluster (TMA)6[Nb10O28]·6H2O (TMA+ = tetramethylammonium cation) was studied theoretically and experimentally. Density functional theory calculations showed that the oxygen atoms in the cluster are highly negatively charged and suggested the possibility that the cluster can act as a base catalyst. We demonstrated for the first time that [Nb10O28]6- actually exhibits base catalytic activity for aldol-type condensation reactions including Knoevenagel and Claisen-Schmidt condensation reactions. The catalytic reactions proceeded under ambient conditions, suggesting that [Nb10O28]6- holds promise as a practical strong base catalyst.

A Paal-Knorr approach to 3,4-diaryl-substituted pyrroles: Facile synthesis of lamellarins O and Q

A very simple, yet efficient synthetic methodology, to obtain 3,4-diaryl-substituted pyrroles is described. The approach is based on the Knoevenagel condensation between arylacetonitriles and substituted aromatic aldehydes, followed by conjugate addition of cyanide to afford succinonitriles in excellent yields. The products thus obtained were subjected to DIBAL-H reduction, followed by cyclization under acidic conditions to produce the corresponding pyrroles in good overall yields. The utility of this protocol is exemplified by the synthesis of the marine alkaloids lamellarins O and Q.

Dialkylamino cyclopentadienyl ruthenium(II) complex-catalyzed α-alkylation of arylacetonitriles with primary alcohols

Aminocyclopentadienyl ruthenium complexes, [(η5-C 5H4NMe2)Ru(PPh3)2(CH 3CN)]+BF4- and [(η5- C5H4NEt2)Ru(PPh3) 2(CH3CN)]+BF4-, are moderately active catalysts for α-alkylation of arylacetonitriles with primary alcohols; on the other hand, the analogous unsubstituted cyclopentadienyl ruthenium complex [(η5-C5H 5)Ru(PPh3)2(CH3CN)] +BF4- shows very low catalytic activity. On the basis of experimental results and theoretical calculations, rationalization for the much higher catalytic activity of the aminocyclopentadienyl complexes over that of the unsubstituted Cp complex is provided. In the catalytic systems with the former, it is possible to regenerate the active solvento complexes via protonation of the metal hydride intermediates and subsequent ligand substitution; this process is, however, very nonfacile in the catalytic system with the latter. The Royal Society of Chemistry 2010.

Heteroaryl β-tetralin ureas as novel antagonists of human TRPV1

We report on a series of α-substituted-β-tetralin-derived and related phenethyl-based isoquinolinyl and hydroxynaphthyl ureas as potent antagonists of the human TRPV1 receptor. The synthesis and Structure-activity relationships (SAR) of the series are described.

Inhibitors of acyl CoA:cholesterol acyltransferase

Conformational restriction of previously disclosed acyclic diphenylethyl)diphenylacetamides led to the discovery of several potent inhibitors of acyl CoA:cholesterol acyltransferase (ACAT). cis-[2-(4- Hydroxyphenyl)-1-indanyl]diphenylacetamide (4a) was the most potent ACAT inhibitor identified (IC50 = 0.04 μM in an in vitro rat hepatic microsomal ACAT assay, ED50 = 0.72 mg/kg/day in cholesterol-fed hamsters).