16424-52-5

Basic information

• Product Name: (E)-6-Phenylhex-5-enenitrile
• Synonyms: (E)-6-Phenylhex-5-enenitrile
• CAS NO: 16424-52-5
• Molecular Weight: 171.242
• Mol File: 16424-52-5.mol

Chemical Properties

• CAS DataBase Reference: (E)-6-Phenylhex-5-enenitrile(CAS DataBase Reference)
• NIST Chemistry Reference: (E)-6-Phenylhex-5-enenitrile(16424-52-5)
• EPA Substance Registry System: (E)-6-Phenylhex-5-enenitrile(16424-52-5)

Safety Data

• Hazardous Substances Data: 16424-52-5(Hazardous Substances Data)

Upstream product

• 2517-76-2 3-iodopropanenitrile 
• 4392-24-9 (Z)-cinnamyl bromide 
• 107-13-1 acrylonitrile 
• 4392-24-9 Cinnamyl bromide 
• 542-76-7 3-Chloropropionitrile 
• 21040-45-9 Cinnamyl acetate 
• 2417-90-5 bromopropionitrile 
• 87802-71-9 (E)-methyl cinnamyl carbonate 
• 4407-36-7 (2E)-3-phenyl-2-propen-1-ol 
• 140-10-3 (E)-3-phenylacrylic acid 
• 621-82-9 Cinnamic acid 
• 100-52-7 benzaldehyde 
• 100-42-5 styrene 
• 2564-83-2 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical 

Downstream Products

• 1613582-64-1 (2S,3R)-N-(4-toluenesulfonyl)-2-phenyl-3-(phenylthio)azepane 
• 16424-56-9 trans 6-phenyl-5-hexenoic acid 

Relevant articles and documents

Vinylboron Self-Promoted Carbonylative Coupling with Cyclobutanone Oxime Esters

Despite the significant progress that has been made in the area of catalyst-dependent chemistry, the exploration of a greener and more environmentally benign catalyst-free reaction remains one of the most important areas in modern chemistry. Herein, we present a vinylboron self-promoted carbonylative coupling with cyclobutanone oxime esters. Various cyclobutanone oxime esters and substituted styrylboronic acids can be transformed into the corresponding enones in moderate to good yields. Detailed EPR investigations and control experiments provide sufficient evidence to show that this reaction goes through a single-electron transfer process.

Synthetic method for preparing gamma-cyano substituted olefin by decarboxylation at room temperature

The invention provides a synthetic method for preparing gamma-cyano substituted olefin by decarboxylation at room temperature, and the method comprises the following steps: reacting unsaturated carboxylic acid and cyclic ketoxime ester in a solvent at room temperature under the promotion of nickel and ruthenium catalysts, ligand and illumination according to the following reaction formula to obtain gamma-cyano substituted olefin. According to the invention, the reaction of unsaturated carboxylic acid and cyclic ketoxime ester under mild conditions is realized for the first time. The method for decarboxylation synthesis of gamma-cyanoolefin has the advantages of mild reaction conditions, convenient operation, excellent functional group compatibility and high reaction yield. Cyano is an important organic structure fragment and widely exists in natural active products and drug molecules. The invention provides a mild, efficient and convenient synthesis method for olefin containing gamma cyano.

Iminyl-Radical-Promoted C-C Bond Cleavage/Heck-Like Coupling via Dual Cobaloxime and Photoredox Catalysis

We report herein an unprecedented protocol for radical-olefin coupling of α-imino-oxy acids and alkenes for the synthesis of alkene-containing nitriles via synergistic photoredox and cobaloxime catalysis. With visible-light irradiation, the transformation

Dual Nickel/Ruthenium Strategy for Photoinduced Decarboxylative Cross-Coupling of α,β-Unsaturated Carboxylic Acids with Cycloketone Oxime Esters

Herein, a dual nickel/ruthenium strategy is developed for photoinduced decarboxylative cross-coupling between α,β-unsaturated carboxylic acids and cycloketone oxime esters. The reaction mechanism is distinct from previous photoinduced decarboxylation of α,β-unsaturated carboxylic acids. This reaction might proceed through a nickelacyclopropane intermediate. The C(sp2)-C(sp3) bond constructed by the aforementioned reaction provides an efficient approach to obtaining various cyanoalkyl alkenes, which are synthetically valuable organic skeletons in organic and medicinal chemistry, under mild reaction conditions. The protocol tolerates many critical functional groups and provides a route for the modification of complex organic molecules.

Tuning the Selectivity of Palladium Catalysts for Hydroformylation and Semihydrogenation of Alkynes: Experimental and Mechanistic Studies

Here, we describe a selective palladium catalyst system for chemodivergent functionalization of alkynes with syngas. In the presence of an advanced ligand L2 bearing 2-pyridyl substituent as a built-in base, either hydroformylation or semihydrogenation of diverse alkynes occurs with high chemo- and stereoselectivity under comparable conditions. Mechanistic studies, including density functional theory (DFT) calculations, kinetic analysis, and control experiments, revealed that the strength and concentration of acidic cocatalysts play a decisive role in controlling the chemoselectivity. DFT studies disclosed that ligand L2 not only promotes heterolytic activation of hydrogen similar to frustrated Lewis pair (FLP) systems in the hydrogenolysis step for hydroformylation but also suppresses CO coordination to promote semihydrogenation under strong acid conditions. This switchable selectivity provides a strategy to design new catalysts for desired products.

Photoredox-Catalyzed Intermolecular Remote C-H and C-C Vinylation via Iminyl Radicals

A unified strategy for intermolecular remote C(sp3)-H and C-C vinylation of O-acyl oximes with vinyl boronic acids has been achieved. This strategy is enabled by photoreductive generation of iminyl radicals from O-acyl oximes under irradiation by visible light. The translocated carbon-centered radicals, which are generated from the iminyl radicals through 1,5-hydrogen atom transfer or C-C cleavage, can be vinylated with vinyl boronic acids. This strategy opens up a new approach to remote functionalization via C(sp3)-H and C-C cleavage and provides an efficient and versatile solution to the synthesis of ?-vinylation of ketones and nitriles.

Copper-Catalyzed Intermolecular Heck-Like Coupling of Cyclobutanone Oximes Initiated by Selective C?C Bond Cleavage

The first example of intermolecular olefination of cyclobutanone oximes with alkenes via selective C?C bond cleavage leading to the synthesis of nitriles in the presence of a cheap copper catalyst is reported. The procedure is distinguished by mild and safe reaction conditions that avoid ligand, oxidant, base, or toxic cyanide salt. A wide scope of cyclobutanones and olefin coupling components can be used without compromising efficiency and scalability. The alternative visible-light-driven photoredox process for this coupling reaction was also uncovered.

Functionalized β-cyclodextrin as supramolecular ligand and their Pd(OAc)2 complex: Highly efficient and reusable catalyst for Mizoroki-Heck cross-coupling reactions in aqueous medium

A novel class of water soluble palladium complexes with recognition abilities based on functionalized β-cyclodextrin has been synthesized. The complex demonstrated high catalytic activity and a supramolecular platform for phosphine-free Mizoroki-Heck cross-coupling reactions in water. The efficient arylation of alkenes was carried out using different iodo- and bromo-arenes with good to excellent yields (up to 96%). The advantages, like recyclability of catalysts, operational simplicity and accessibility in aqueous medium, make this protocol eco-friendly.

Lewis base catalyzed, enantioselective, intramolecular sulfenoamination of olefins

A method for the enantioselective, intramolecular sulfenoamination of various olefins has been developed using a chiral BINAM-based selenophosphoramide, Lewis base catalyst. Terminal and trans disubstituted alkenes afforded pyrrolidines, piperidines, and