495-10-3

Upstream product

• 50-00-0 formaldehyd 
• 917-58-8 potassium ethoxide 
• 140-29-4 phenylacetonitrile 
• 74-89-5 methylamine 
• 29624-91-7 1-cyano-1-phenylethyl acetate 
• 123-31-9 hydroquinone 
• 98-81-7 1-bromovinylbenzene 
• 151-50-8 potassium cyanide 
• 75-86-5 2-hydroxy-2-methylpropanenitrile 
• 536-74-3 phenylacetylene 
• 74-90-8 hydrogen cyanide 
• 544-92-3 copper(I) cyanide 
• 52923-48-5 3-hydroxy-2-phenylpropanenitrile 
• 76-02-8 trifluoroacetyl chloride 

Downstream Products

• 100705-29-1 3-butylsulfanyl-2-phenyl-propionitrile 
• 101889-83-2 3c-(6-methoxy-2,3,4-trimethyl-phenyl)-2-phenyl-acrylonitrile 
• 25679-87-2 1,2,3,4-Tetrahydro-1,4-dicyano-1-phenylnaphthalene 
• 2873-99-6 3-dimethylamino-2-phenyl-propionitrile 
• 92651-62-2 4-isopropyl-5-oxo-2-phenyl-hexanenitrile 
• 54248-06-5 5-oxo-2-phenylhexanenitrile 
• 93477-43-1 4-acetyl-2-phenyl-nonanenitrile 
• 91956-53-5 4-methyl-5-oxo-2-phenyl-hexanenitrile 
• 3755-93-9 (+/-)-2,6-Dimethyl-5-oxo-2-phenyl-heptansaeure-nitril 
• 4361-42-6 3-Cyclohexyl-2-phenylpropiononitril 
• 1823-91-2 1-phenylethyl cyanide 
• 94812-96-1 2-Methyl-2-<(2-cyano-2-phenyl)ethyl>-1,3-cyclopentanedione 
• 39822-26-9 (E)-2-cyano-2-phenylcyclopropanecarboxylic acid methyl ester 
• 58559-95-8 (Z)-α-Cyano-β-nitrostyrol 

Relevant academic research and scientific papers

Photocatalytic Hydromethylation and Hydroalkylation of Olefins Enabled by Titanium Dioxide Mediated Decarboxylation

A versatile method for the hydromethylation and hydroalkylation of alkenes at room temperature is achieved by using the photooxidative redox capacity of the valence band of anatase titanium dioxide (TiO2). Mechanistic studies support a radical-based mechanism involving the photoexcitation of TiO2 with 390 nm light in the presence of acetic acid and other carboxylic acids to generate methyl and alkyl radicals, respectively, without the need for stoichiometric base. This protocol is accepting of a broad scope of alkene and carboxylic acids, including challenging ones that produce highly reactive primary alkyl radicals and those containing functional groups that are susceptible to nucleophilic substitution such as alkyl halides. This methodology highlights the utility of using heterogeneous semiconductor photocatalysts such as TiO2 for promoting challenging organic syntheses that rely on highly reactive intermediates.

Bromomethyl Silicate: A Robust Methylene Transfer Reagent for Radical-Polar Crossover Cyclopropanation of Alkenes

A general protocol for visible-light-induced cyclopropanation of alkenes was developed with bromomethyl silicate as a methylene transfer reagent, offering a robust tool for accessing highly valuable cyclopropanes. In addition to α-aryl or methyl-substituted Michael acceptors and styrene derivatives, the unactivated 1,1-dialkyl ethylenes were also shown to be viable substrates. Apart from realizing the cyclopropanation of terminal alkenes, the methyl transfer reaction has been further demonstrated to be amenable to the internal olefins. The photocatalytic cyclopropanation of 1,3-bis(1-arylethenyl)benzenes was also achieved, giving polycyclopropane derivatives in excellent yields. With late-stage cyclopropanation as the key strategy, the synthetic utility of this transformation was also demonstrated by the total synthesis of LG100268.

Preparation method for 2-phenylacrylonitrile

The invention discloses a preparation method for 2-phenylacrylonitrile. Benzyl cyanide and paraformaldehyde are used as raw materials. The preparation method comprises the following steps: 1) enablingthe benzyl cyanide, the paraformaldehyde, an acid-bindi

Nickel-catalyzed regioselective hydrocyanation of terminal alkynes by assistance of a tosyl group

Nickel-catalyzed regioselective hydrocyanation of terminal alkynes is described. A tosylamide functionality at the propargyl position was the most suitable group for controlling the regiochemistry for C–CN bond formation as well as rate enhancement. A gram-scale synthesis was achieved by minimizing the catalyst loading to 2 mol%. The major HCN adduct could be transformed to the corresponding indoline through construction of a benzylic quaternary carbon under iron catalysis.

Polymer biquinolyl-containing complexes of Pd(ii) as efficient catalysts for cyanation of aryl and vinyl halides with K4Fe(CN)6

A catalytic system for cyanation of aryl and vinyl halides with K4Fe(CN)6 based on a structurally tunable and nontoxic polymer backbone of polyamic type with biquinolyl fragments in the polymer chain capable of coordination to PdII ions is developed. The catalyst is eligible for thermal and microwave activation; in the latter case the reaction time is dramatically decreased. Cyanation of vinyl bromides occurs stereoselectively, and the configuration of the starting alkene is retained; even for Z-isomers the impact of configuration inversion is less than 5%. The polymer-based Pd catalyst is applicable for one-pot multi-step synthesis of the precursors of mesogenic structures of biphenyl type. Consecutive cross-coupling and cyanation reactions can be performed in the presence of the same portion of catalyst, in the same solvent, without isolation of intermediate products.

Straightforward synthesis of 1,2-dicyanoalkanes from nitroalkenes and silyl cyanide mediated by tetrabutylammonium fluoride

A straightforward synthesis of 1,2-dicyanoalkanes by reacting nitroalkenes with trimethylsilyl cyanide in the presence of tetrabutylammonium fluoride is described. The reaction proceeds through a tandem double Michael addition under mild conditions. Employing the hypervalent silicate generated from trimethylsilyl cyanide and tetrabutylammonium fluoride is essential for achieving this transformation. Mechanistic studies suggest that a small amount of water included in the reaction media plays a key role. This protocol is applicable to various types of substrates including electron-rich and electron-deficient aromatic nitroalkenes, and aliphatic nitroalkenes. Moreover, vinyl sulfones were found to be good alternatives, particularly for electron-deficient nitroalkenes. The broad substrate scope and functional group tolerance of the reaction makes this approach a practical method for the synthesis of valuable 1,2-dicyanoalkanes.

Enantioselective synthesis of (R)-2-arylpropanenitriles catalysed by ene-reductases in aqueous media and in biphasic ionic liquid-water systems

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.

Suzuki coupling of 2-chloroacrylonitrile, methyl 2-chloroacrylate, or 2-chloroprop-1-en-3-ol with arylboronic acids catalyzed by a palladium-tetraphosphine complex

The tetraphosphine all-cis-1,2,3,4-tetrakis(diphenylphosphinomethyl) cyclopentane (Tedicyp) in combination with [Pd(C3H 5)Cl]2 affords an efficient catalyst of the coupling of 2-chloroacrylonitrile with arylboronic acids.

Nucleosides. Part LXIV. Base-Labile Protecting Groups for the Oligoribonucleotide Synthesis

New labile protecting groups for the anticipated synthesis of oligoribonucleotides were developed and introduced via their carbonochloridates 8-11 at the 5'-O position of thymidine (15) to form 16, 18, 21, and 24 in good yields (Schemes 2 and 3). Similarly, the 5'-O-diphenylphosphinoyl(dpp)-protected thymidine derivative 27 was synthesized with diphenylphosphinoyl chloride 14 as the reactive reagent. With the help of the model compounds 16, 18, 21, 24, and 27, the deprotection rates of these functions towards base treatment were recorded to evaluate their usefulness as temporary protecting groups in RNA assembly (Table). Finally, the relative stability of the 2-(4-nitrophenyl)ethoxycarbonyl (npeoc) protecting group towards bases confirmed its use as a permanent blocking group in our npe/npeoc strategy.

Novel isomerization reaction of N,N-dimethyl-α-(methoxycarbonyl)-4- substituted-benzylammonium N-methylides

Fluoride ion-induced desilylation of N,N-dimethyl-N- [(trimethylsilyl)methyl]-α-(methoxycarbonyl)4-substituted benzylammonium salts (7) gave two Stevens rearrangement products: methyl 3-(dimethylamino)- 2-(4-substituted phenyl)propionates (13) from N-methylides 8, and methyl 3- (dimethylamino)-3-(4-substituted phenyl)propionates (15) from N-benzylides 10. Additional Stevens rearrangement products, methyl 2-(dimethylamino)-3- (4-substituted phenyl)propionates (16), were competitively formed from ylides 12 when the cesium fluoride used was not predried. The mechanism of the isomerization from methylides 8, which was initially generated, to 10 and 12 is discussed.