53243-59-7

Usage

Uses

Used in Organic Synthesis:
(Z)-3-methyl-5-phenylpent-2-enenitrile is used as a versatile intermediate in organic synthesis for its ability to participate in a wide range of chemical reactions, facilitating the creation of more complex compounds.
Used in Pharmaceutical Production:
In the pharmaceutical industry, (Z)-3-methyl-5-phenylpent-2-enenitrile is used as a key building block for the synthesis of various pharmaceuticals, owing to its unique chemical reactivity and structural properties that can be leveraged to develop new medicinal compounds.
Used in Agrochemical Production:
Similarly, in agrochemicals, (Z)-3-methyl-5-phenylpent-2-enenitrile serves as an important intermediate, contributing to the development of effective and novel agrochemical products that can enhance crop protection and yield.
Used in the Production of Fine Chemicals:
(Z)-3-methyl-5-phenylpent-2-enenitrile is also utilized in the manufacture of fine chemicals, where its unique structural attributes and reactivity are harnessed to produce specialty chemicals for specific applications in various industries.

InChI:InChI=1/C12H13N/c1-11(9-10-13)7-8-12-5-3-2-4-6-12/h2-6,9H,7-8H2,1H3/b11-9-

Upstream product

• 2537-48-6 diethyl 1-cyanomethylphosphonate 
• 2550-26-7 4-Phenyl-2-butanone 
• 928-53-0 maleonitrile 
• 72485-49-5 (E)-(3-methylpent-3-en-1-yl)benzene 
• 72485-50-8 (Z)-(3-methylpent-3-en-1-yl)benzene 

Relevant academic research and scientific papers

E- and Z-, di- and tri-substituted alkenyl nitriles through catalytic cross-metathesis

Nitriles are found in many bioactive compounds, and are among the most versatile functional groups in organic chemistry. Despite many notable recent advances, however, there are no approaches that may be used for the preparation of di- or tri-substituted alkenyl nitriles. Related approaches that are broad in scope and can deliver the desired products in high stereoisomeric purity are especially scarce. Here, we describe the development of several efficient catalytic cross-metathesis strategies, which provide direct access to a considerable range of Z- or E-di-substituted cyano-substituted alkenes or their corresponding tri-substituted variants. Depending on the reaction type, a molybdenum-based monoaryloxide pyrrolide or chloride (MAC) complex may be the optimal choice. The utility of the approach, enhanced by an easy to apply protocol for utilization of substrates bearing an alcohol or a carboxylic acid moiety, is highlighted in the context of applications to the synthesis of biologically active compounds.

Chemoselective silylative reduction of conjugated nitriles under metal-free catalytic conditions: β-silyl amines and enamines

Abstract The B(C6F5)3-catalyzed silylative reduction of conjugated nitriles has been developed to afford synthetically valuable β-silyl amines. The reaction is chemoselective and proceeds under mild conditions. Mechanistic elucidation indicates that it proceeds by rapid double hydrosilylation of the conjugated nitrile to an enamine intermediate which is subsequently reduced to the β-silyl amine, thus forming a new C(sp3)-Si bond. Based on this mechanistic understanding, a preparative route to enamines was also established using bulky silanes. Triple whammy: The B(C6F5)3-catalyzed silylative reduction of conjugated nitriles has been developed to afford synthetically valuable β-silyl amines. Based on the mechanistic understanding, a preparative route to enamines was also established using bulky silanes. The reaction is chemoselective, has a broad scope, and proceeds under mild reaction conditions. The mechanism of the triple hydrosilylation is discussed.

Asymmetric hydrogenation of α,β-unsaturated nitriles with base-activated iridium N,P ligand complexes

Although many chiral catalysts are known that allow highly enantioselective hydrogenation of a wide range of olefins, no suitable catalysts for the asymmetric hydrogenation of α,β-unsaturated nitriles have been reported so far. We have found that Ir N,P ligand complexes, which under normal conditions do not show any reactivity towards α,β-unsaturated nitriles, become highly active catalysts upon addition of N,N- diisopropylethylamine. The base-activated catalysts enable conjugate reduction of α,β-unsaturated nitriles with H2 at low catalyst loadings, affording the corresponding saturated nitriles with high conversion and excellent enantioselectivity. In contrast, alkenes lacking a conjugated cyano group do not react under these conditions, making it possible to selectively reduce the conjugated C=C bond of an α,β-unsaturated nitrile, while leaving other types of C=C bonds in the molecule intact.

82. Enantioselective reduction of electrophilic C=C bonds with sodium tetrahydroborate and 'semicorrin' cobalt catalysts

'Semicorrin' cobalt complexes, prepared in situ from cobalt(II) chloride and the corresponding ligands, are efficient catalysts for the enantioselective reduction of electrophilic C=C bonds with NaBH4. The best selectivities (> 90% ee) are achieved with α,β-unsaturated carboxamides and carboxylates. Analogous α,β-unsaturated nitriles, sulfones, and phosphonates afford enantiomenc excesses of 50-70%. Interestingly, in the reduction of α,β-unsaturated sulfones, the highest enantioselectivities were obtained with unsymmetrical 'semicorrins', whereas in all other cases C2-symmetric 'semicorrins' proved to be superior.

Nitriles with odorant properties

Compound of the formula STR1 in which n stands for 0 or 1 and, where "n" stands for 0, a double bond is present as indicated by the chain line, and R represents a cyclohexyl radical, or a phenyl radical which may optionally be substituted in the p-position by a lower alkyl radical. The compounds are produced by reaction of methylethyl ketone substituted in the β-position by R with cyanoacetic acid in the presence of a basic catalyst. The compounds are useful as perfumes.