5558-42-9

Upstream product

• 140-29-4 phenylacetonitrile 
• 103-63-9 1-phenyl-2-bromoethane 
• 104-53-0 3-phenyl-propionaldehyde 
• 98-80-6 phenylboronic acid 
• 60-12-8 2-phenylethanol 
• 112529-00-7 (E)-2,4-diphenylbut-3-enenitrile 
• 4363-35-3 Dihydroxy-styryl-boran 
• 78782-27-1 4,4,5,5-tetramethyl-2-styryl-[1,3,2]dioxaborolane 
• 111571-93-8 (Z)-2,4-diphenylbut-2-enenitrile 
• 100-52-7 benzaldehyde 
• 532-28-5 (RS)-mandelonitrile 
• 536-74-3 phenylacetylene 

Downstream Products

• 4444-70-6 (2,4-diphenylbutyl)amine 
• 15144-49-7 5-Chlor-2-phenaethyl-2-phenyl-valeronitril 
• 15144-57-7 2.6-Bis--2.6-diphenyl-pimelinsaeuredinitril 
• 7498-87-5 2-phenyl-3,4-dihydro-2H-naphthalen-1-one 
• 28717-84-2 7-chloro-3-phenyl-2,3,4,5-tetrahydro-1H-1-benzazepin-2-one 
• 3300-62-7 3-phenyl-2,3,4,5-tetrahydro-1H-1-benzazepin-2-one 
• 21460-77-5 2,4-diphenyl-butyryl chloride 
• 20495-17-4 2-phenyl-1-tetralone oxime 
• 111027-00-0 7-bromo-3-phenyl-2,3,4,5-tetrahydro-1H-1-benzazepin-2-one 
• 1431331-58-6 C₂₆H₂₄Cl₂N₄ 
• 2901-34-0 2,4-diphenylbutanoic acid 

Relevant academic research and scientific papers

Synthesis of Acrylonitriles via Mild Base Promoted Tandem Nucleophilic Substitution-Isomerization of α-Cyanohydrin Methanesulfonates

Main observation and conclusion: We have developed an efficient synthesis of acrylonitriles via mild base promoted tandem nucleophilic substitution-isomerization of α-cyanohydrin methanesulfonates with alkenylboronic acids. This transition metal-free protocol works under simple and mild conditions and offers good chemical yields for a wide range of substrates and demonstrates good functional group tolerance. (Figure presented.).

Base-controlled chemoselectivity: direct coupling of alcohols and acetonitriles to synthesise α-alkylated arylacetonitriles or acetamides

We achieved chemoselective synthesis of α-alkylated arylacetonitriles and acetamides by combining Ir complex-catalysed direct coupling of alcohols and nitriles by a simple adjustment of the base. Methanol and ethanol performed well as the alkylating reagents. This method of acetonitrile alkylation provided a novel approach for carbon chain extension.

Iron-Catalyzed Alkylation of Nitriles with Alcohols

A general, efficient iron-catalyzed α-alkylation of nitriles with primary alcohols through a hydrogen-borrowing pathway has been developed, allowing a wide variety of alkylated nitriles to be readily accessible. Detailed mechanistic studies suggest that the reaction proceeds via an olefin intermediate with the turnover rate limited by the hydrogenation of the olefin with an iron hydride. Apart from participating in the alkylation, the nitrile is found to play an important role in promoting the formation of and stabilizing the active catalytic species.

Atmosphere-Controlled Chemoselectivity: Rhodium-Catalyzed Alkylation and Olefination of Alkylnitriles with Alcohols

The chemoselective alkylation and olefination of alkylnitriles with alcohols have been developed by simply controlling the reaction atmosphere. A binuclear rhodium complex catalyzes the alkylation reaction under argon through a hydrogen-borrowing pathway and the olefination reaction under oxygen through aerobic dehydrogenation. Broad substrate scope is demonstrated, permitting the synthesis of some important organic building blocks. Mechanistic studies suggest that the alkylation product may be formed through conjugate reduction of an alkene intermediate by a rhodium hydride, whereas the formation of olefin product may be due to the oxidation of the rhodium hydride complex with molecular oxygen.

Synthesis of α-aryl esters and nitriles: Deaminative coupling of α-aminoesters and α-aminoacetonitriles with arylboronic acids

Transition-metal-free synthesis of α-aryl esters and nitriles using arylboronic acids with α-aminoesters and α-aminoacetonitriles, respectively, as the starting materials has been developed. The reaction represents a rare case of converting C(sp3)-N bonds into C(sp3)-C(sp2) bonds. The reaction conditions are mild, demonstrate good functional-group tolerance, and can be scaled up. Touch base: A transition-metal-free protocol for the synthesis of α-aryl esters and nitriles by deaminative coupling is presented. Strong bases and transition-metal catalysts are not needed. The new synthetic method uses readily available starting materials and demonstrates wide substrate scope.

Pyridinylpyrimidines selectively inhibit human methionine aminopeptidase-1

Cellular protein synthesis is initiated with methionine in eukaryotes with few exceptions. Methionine aminopeptidases (MetAPs) which catalyze the process of N-terminal methionine excision are essential for all organisms. In mammals, type 2 MetAP (MetAP2)

Studies in polyphenol chemistry and bioactivity. 2. Establishment of interflavan linkage regio- and stereochemistry by oxidative degradation of an O-alkylated derivative of procyanidin B2 to (R)-(-)-2,4-diphenylbutyric acid

The assignment of interflavan bond regio- and stereochemistry in oligomeric proanthocyanidins has in the past relied on empirical spectroscopic techniques which are influenced by the conformation of the C rings. Only recently was the 4,8-regiochemistry of procyanidin B2 (3b) firmly established by 2-dimensional NMR methods. We describe herein the proof of 4β-stereochemistry in 3b by oxidative degradation of the derivative 3d bearing differential (O-benzyl and O-methyl) protecting groups in its 'top' and 'bottom' epicatechin moieties, to (R)-(-)-2,4-diphenylbutyric acid. The key elements of the degradative process are (1) removal of the C-3 alcohol functions through a modified Barton deoxygenation employing hypophosphorous acid as the reducing agent; (2) deprotection of the 'top' unit by hydrogenolysis, followed by exhaustive aryl triflate formation with N,N-bis-(trifluoromethanesulfonyl)aniline and DBU in DMF; (3) hydrogenolytic deoxygenation of the 'top' unit over Pearlman's catalyst with concomitant scission of the O-C2 bond; (4) selective oxidation of the 'bottom' unit with NaIO4/RuCl3. The hitherto unreported absolute configuration of (-)-2,4-diphenylbutyric acid was established as R by X-ray crystal structure analysis of the (R)-(+)-α-methylbenzylamine salt. As a corollary, the selectivity of hydrogenolytic and solvolytic reactions of epicatechin-derived tetrasulfonates has been investigated.

A novel class of potential central nervous system agents. 3-Phenyl-2-(1-piperazinyl)-5H-1-benzazepines

A series of 3-phenyl-2-piperazinyl-5H-1-benzazepines and related compounds were synthesized and evaluated for potential neuroleptic activity. The preparation of these compounds was carried out by 2,3-dichlorination of 3-phenyl-2,3,4,5-tetrahydro-1H-1-benz