53243-60-0

Usage

Uses

Used in Organic Synthesis:
(E)-3-methyl-5-phenylpent-2-enenitrile is used as a building block in organic synthesis for the creation of various chemical compounds. Its unique structure allows for the formation of new molecules with different properties and applications.
Used in Pharmaceutical Production:
In the pharmaceutical industry, (E)-3-methyl-5-phenylpent-2-enenitrile is used as a chemical intermediate. Its role in the synthesis of various drugs makes it a valuable component in the development of new medications.
Used in Agrochemicals:
(E)-3-methyl-5-phenylpent-2-enenitrile is also utilized in the production of agrochemicals, which are chemicals specifically designed to benefit crop production. Its contribution to the development of these products highlights its importance in the agricultural sector.
Used in Dye Production:
(E)-3-methyl-5-phenylpent-2-enenitrile is used as a chemical intermediate in the production of dyes. Its involvement in the creation of various dyes for different industries, such as textiles and plastics, showcases its versatility.
Used in Perfumery:
(E)-3-methyl-5-phenylpent-2-enenitrile is employed in the perfume industry as a component in the synthesis of various fragrances. Its unique chemical properties contribute to the creation of distinct and appealing scents.
Used in Industrial Chemicals:
In addition to its applications in dyes and perfumes, (E)-3-methyl-5-phenylpent-2-enenitrile is also used as a chemical intermediate in the production of other industrial chemicals. Its role in the synthesis of these chemicals further emphasizes its importance in various industries.
Safety Precautions:
Due to its potential hazards and toxicological properties, (E)-3-methyl-5-phenylpent-2-enenitrile should be handled with care. Proper safety measures and handling protocols should be followed to minimize risks associated with its use.

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

• 928-53-0 maleonitrile 
• 72485-50-8 (Z)-(3-methylpent-3-en-1-yl)benzene 
• 72485-49-5 (E)-(3-methylpent-3-en-1-yl)benzene 
• 72681-06-2 (E)-3-methyl-5-phenyl-2-penteneamide 
• 72681-05-1 (E/Z)-3-methyl-5-phenylpent-2-enoic acid 
• 36805-43-3 ethyl (E)-3-methyl-5-phenylpent-2-enoate 
• 2550-26-7 4-Phenyl-2-butanone 
• 2537-48-6 diethyl 1-cyanomethylphosphonate 

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.

Highly efficient Rh-catalyzed asymmetric hydrogenation of α,β-unsaturated nitriles

A highly efficient enantioselective hydrogenation of α,β-unsaturated nitriles catalyzed by Rh-(R,R)-f-spiroPhos complex has been developed. With Rh-(R,R)-f-spiroPhos catalyst and under mild conditions, a wide range of α,β-unsaturated nitriles including the (E)- and (Z)-isomers of 3-alkyl-3-aryl, 3,3-diaryl, and 3,3-dialkyl α,β-unsaturated nitriles were hydrogenated to the corresponding chiral nitriles with excellent enantioselectivities (up to 99.9% ee) and high turnover numbers (TON up to 10,000).

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.

Ketone precursors for organoleptic compounds

The invention discloses ketones of formula I: wherein, Y is an optionally substituted alkyl, cycloalkyl, or cycloalkylalkyl, wherein each alkyl group is straight or branched and each alkyl and cycloalkyl group is saturated or unsaturated; R1is hydrogen or a C1-6alkyl group that is substituted, saturated or unsaturated, straight or branched; A is a chromophoric substituted aromatic ring or ring system; n is an integer; and with the proviso that formula I is not 2-ethoxy-1-phenyl-ethanone. These compositions are useful for the delivery of organoleptic compounds, especially of flavors, fragrances, masking agents and antimicrobial compounds.

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.