27179-74-4Relevant academic research and scientific papers
Method for preparing alkenyl cyanide compounds
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Paragraph 0100; 0130; 0146-0148, (2019/10/23)
The invention discloses a method for preparing alkenyl cyanide compounds represented by formula II. Alkynes represented by formula I and a cyanation reagent are subjected to a reduction reaction represented by a formula shown in the description in an organic solvent under the protection of a gas at 20-100 DEG C under the action of a nickel catalyst, a reducing agent and H2O to prepare the alkenyl cyanide compounds represented by formula II. The preparation method of the invention, which adopts the cheap nickel as the catalytic system, has the advantages of simplicity in operation, mild reaction conditions, good compatibility of functional groups, wide application range of the substrate, high reaction efficiency and high yield, so the method has high application and promotion values.
Direct Access to Versatile Electrophiles via Catalytic Oxidative Cyanation of Alkenes
Gao, De-Wei,Vinogradova, Ekaterina V.,Nimmagadda, Sri Krishna,Medina, Jose M.,Xiao, Yiyang,Suciu, Radu M.,Cravatt, Benjamin F.,Engle, Keary M.
supporting information, p. 8069 - 8073 (2018/06/22)
Nucleophilic attack on carbon-based electrophiles is a central reactivity paradigm in chemistry and biology. The steric and electronic properties of the electrophile dictate its reactivity with different nucleophiles of interest, allowing the opportunity to fine-tune electrophiles for use as coupling partners in multistep organic synthesis or for covalent modification of proteins in drug discovery. Reactions that directly transform inexpensive chemical feedstocks into versatile carbon electrophiles would therefore be highly enabling. Herein, we report the catalytic, regioselective oxidative cyanation of conjugated and nonconjugated alkenes using a homogeneous copper catalyst and a bystanding N-F oxidant to furnish branched alkenyl nitriles that are difficult to prepare using existing methods. We show that the alkenyl nitrile products serve as electrophilic reaction partners for both organic synthesis and the chemical proteomic discovery of covalent protein ligands.
Nickel-Catalyzed Highly Regioselective Hydrocyanation of Terminal Alkynes with Zn(CN)2 Using Water as the Hydrogen Source
Zhang, Xingjie,Xie, Xin,Liu, Yuanhong
supporting information, p. 7385 - 7389 (2018/06/11)
The first efficient and general nickel-catalyzed hydrocyanation of terminal alkynes with Zn(CN)2 in the presence of water has been developed. The reaction provides a regioselective protocol for the synthesis of functionalized vinyl nitriles with a range of structural diversity under mild reaction conditions while obviating use of the volatile and hazardous reagent of HCN. Deuterium-labeling experiments confirmed the role of water as the hydrogen source in this hydrocyanation reaction.
Enantioselective synthesis of (R)-2-arylpropanenitriles catalysed by ene-reductases in aqueous media and in biphasic ionic liquid-water systems
Brenna, Elisabetta,Crotti, Michele,Gatti, Francesco G.,Manfredi, Alessia,Monti, Daniela,Parmeggiani, Fabio,Santangelo, Sara,Zampieri, Davila
, p. 2425 - 2431 (2014/08/18)
The enantioselective reduction of α-methylene nitrile derivatives catalysed by ene-reductases affords the corresponding (R)-2-arylpropanenitriles with high conversion values. The reaction is investigated either in aqueous medium (with an organic cosolvent or by loading the substrate onto hydrophobic resins) or in a biphasic ionic liquid-water system. The use of ionic liquids, herein with isolated ene-reductases, is found to improve the work-up and the substrate recovery method. The synthetic manipulation of the final chiral nitrile derivatives indicates how this biocatalysed method can be exploited for the preparation of a wide range of chiral compounds.
Esters of 2-phenylalkanenitriles and antifungal compositions containing them
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Page/Page column 4; 5, (2008/12/06)
Esters of 2-phenylalkanenitriles, such as 3-acetoxy-2-(2-chloro-5-(difluoromethoxy)phenyl)propanenitrile and 3-acetoxy-2-(4-chlorophenyl)propanenitrile, and compositions containing such esters, are useful as fungicides at very low concentrations.
The Synthesis of Phosphonobaclofen, an Antagonist of Baclofen
Chiefari, John,Galanopoulos, Speros,Janowski, Wit K.,Kerr, David I. B.,Prager, Rolf H.
, p. 1511 - 1518 (2007/10/02)
Phosphonobaclofen 3-amino-2-(4-chlorophenyl)propylphosphonic acid, has been synthesized in five steps from ethyl 3-(4-chlorophenyl)but-2-enoate, and is a specific antagonist of baclofen.The alternative synthetic pathways, involving conjugate addition of phosphite to 2-(4-chlorophenyl)propenenitrile and of cyanide to 2-(4-chlorophenyl)ethylphosphonate ester, failed.Cyanide ion did add efficiently to ethyl 3-(4-chlorophenyl)-2-diethoxyphosphinylprop-2-enoate and hydrogenation followed by hydrolysis of the product gave (2 S, 3 S)- and (2R, 3 R)-4-amino-3-(4-chlorophenyl)-2-phosphonobutanoic acid, which is also undergoing pharmacological evaluation.
