6308-98-1

Usage

InChI:InChI=1/C16H19N/c1-3-7-15(8-4-1)11-13-17-14-12-16-9-5-2-6-10-16/h1-10,17H,11-14H2

Upstream product

• 122-78-1 phenylacetaldehyde 
• 64-04-0 phenethylamine 
• 140-29-4 phenylacetonitrile 
• 142-84-7 di-n-propylamine 
• 64-19-7 acetic acid 
• 124-40-3 dimethyl amine 
• 109-89-7 diethylamine 
• 622-24-2 2-phenylethyl chloride 
• 103-63-9 1-phenyl-2-bromoethane 
• 100-51-6 benzyl alcohol 
• 645-54-5 2-phenylthioacetamide 
• 85608-05-5 Diphenethyl-carbamic acid ethyl ester 
• 7732-18-5 water 
• 29883-15-6 amygdalin 

Downstream Products

• 115419-49-3 N-phenyl-N-(2-phenylethyl)aniline 
• 861786-91-6 N,N-diphenethyl-benzamide 
• 109652-40-6 allyl-diphenethyl-amine 
• 25413-78-9 nitroso-diphenethyl-amine 
• 100-41-4 ethylbenzene 
• 7664-41-7 ammonia 
• 932005-76-0 phenethyl-(1,1,3,3-tetramethyl-butyl)-amine 
• 3647-71-0 N-benzyl-2-phenylethylamine 

Relevant academic research and scientific papers

Photoinduced electron-transfer reaction of α-bromomethyl-substituted benzocyclic β-keto esters with amines: Selective reaction pathways depending on the nature of the amine radical cations

Photoinduced electron-transfer reaction of α-bromomethyl-substituted benzocyclic β-keto esters with tertiary amines was investigated. Debrominated β-keto esters and ring-expanded γ-keto esters were obtained as major products. On the basis of mechanistic experiments it was concluded that these products are formed via a reaction sequence of selective carbon-bromine bond cleavage and subsequent competitive hydrogen abstraction and Dowd-Beckwith ring-expansion of the resulting primary alkyl radicals. The characteristic product distribution observed for the type of amine used is rationalized on the basis of selective reaction pathways of generated radical intermediates that depend on the nature of the amine radical cations.

A potassium magnesiate complex: Synthesis, structure and catalytic intermolecular hydroamination of styrenes

A new heterobimetallic potassium magnesiate complex KMg[N(SiMe3)2]2Bn (Bn = PhCH2-) was synthesized by simply mixing magnesium amide and potassium benzyl in toluene. The TMEDA-ligated potassium magnesiate comple

Method for synthesizing dibenzylamine compound by selective hydrogenation of photocatalytic benzonitrile compound

The invention belongs to the technical field of selective catalytic hydrogenation, and particularly relates to a method for synthesizing a dibenzylamine compound through selective hydrogenation of a photocatalytic benzonitrile compound, wherein the photocatalyst is prepared from silicon carbide with high specific surface area (specific surface area 20 - 100m). 2 Metal Platinum as a carrier load mass fraction 0.1-20%, the metal nanoparticles being less than 200 nanometers ?. g. After mixing the benzonitrile compound and the solvent at 0.01 - 0.6 mass ratio, the catalyst was added, and the hydrogen pressure was maintained between 0.1 mpa - 2 mpa under hydrogen atmosphere and the reaction was stirred while maintaining the temperature of the reaction system was 10 - 100 °C and the strength was 0.01 - 5W/cm. 2 Under the light intensity of the reaction 0.5 - 12h, the target product can be obtained. The method has the most remarkable characteristics of being capable of effectively utilizing light to promote reaction and high in reaction rate.

Structure-Activity Relationship Studies of Pyrimidine-4-Carboxamides as Inhibitors of N-Acylphosphatidylethanolamine Phospholipase D

N-Acylphosphatidylethanolamine phospholipase D (NAPE-PLD) is regarded as the main enzyme responsible for the biosynthesis of N-acylethanolamines (NAEs), a family of bioactive lipid mediators. Previously, we reported N-(cyclopropylmethyl)-6-((S)-3-hydroxypyrrolidin-1-yl)-2-((S)-3-phenylpiperidin-1-yl)pyrimidine-4-carboxamide (1, LEI-401) as the first potent and selective NAPE-PLD inhibitor that decreased NAEs in the brains of freely moving mice and modulated emotional behavior [ Mock et al. Nat Chem. Biol., 2020, 16, 667-675 ]. Here, we describe the structure-activity relationship (SAR) of a library of pyrimidine-4-carboxamides as inhibitors of NAPE-PLD that led to the identification of LEI-401. A high-throughput screening hit was modified at three different substituents to optimize its potency and lipophilicity. Conformational restriction of an N-methylphenethylamine group by replacement with an (S)-3-phenylpiperidine increased the inhibitory potency 3-fold. Exchange of a morpholine substituent for an (S)-3-hydroxypyrrolidine reduced the lipophilicity and further increased activity by 10-fold, affording LEI-401 as a nanomolar potent inhibitor with drug-like properties. LEI-401 is a suitable pharmacological tool compound to investigate NAPE-PLD function in vitro and in vivo.

Rhodium-Catalyzed Anti-Markovnikov Hydroamination of Aliphatic and Aromatic Terminal Alkynes with Aliphatic Primary Amines

Anti-Markovnikov hydroamination of both aliphatic and aromatic terminal alkynes with primary amines was achieved using an 8-quinolinolato rhodium catalyst to form aldimines and enamines in high yields. This catalytic system realized high functional group tolerance including hydroxy, bromo, cyano, and thioester groups.

Selective Synthesis of Symmetrical Secondary Amines from Nitriles with a Pt?CuFe/Fe3O4 Catalyst and Ammonia Borane as Hydrogen Donor

Hydrogenation of nitriles is an efficient and environmentally friendly route to synthesize symmetrical secondary amines, but it usually produces a mixture of amines, imines, and hydrogenolysis by-products. Herein we report a magnetic quaternary-component Pt?CuFe/Fe3O4 nanocatalyst system for the selective synthesis of symmetrical secondary amines with ammonia borane as hydrogen donor. The catalyst with a low Pt loading (0.456 wt%) is the source of the activity, and the d-band electron transfer from Cu to Fe enhances the selectivity. This synergistic effect results in the transformation of benzonitrile to dibenzylamine with excellent conversion (up to 99 %) and nearly quantitative selectivity (up to 96 %) under mild reaction conditions, nevertheless, the reaction TOF is as high as up to 1409.9 h?1. A variety of nitriles are suitable for the synthesis of symmetrical secondary amines. More importantly, unwanted hydrogenolysis byproducts, especially toluene, is not detected at all. In addition, the catalyst is magnetically recoverable, and it can be reused up to five times.

Catalytic Hydrogenation of Thioesters, Thiocarbamates, and Thioamides

Direct hydrogenation of thioesters with H2 provides a facile and waste-free method to access alcohols and thiols. However, no report of this reaction is documented, possibly because of the incompatibility of the generated thiol with typical hydrogenation catalysts. Here, we report an efficient and selective hydrogenation of thioesters. The reaction is catalyzed by an acridine-based ruthenium complex without additives. Various thioesters were fully hydrogenated to the corresponding alcohols and thiols with excellent tolerance for amide, ester, and carboxylic acid groups. Thiocarbamates and thioamides also undergo hydrogenation under similar conditions, substantially extending the application of hydrogenation of organosulfur compounds.

Cine-Silylative Ring-Opening of α-Methyl Azacycles Enabled by the Silylium-Induced C-N Bond Cleavage

Described herein is the development of a borane-catalyzed cine-silylative ring-opening of α-methyl azacycles. This transformation involves four-step cascade processes: (i) exo-dehydrogenation of alicyclic amine, (ii) hydrosilylation of the resultant enamine, (iii) silylium-induced cis-β-amino elimination to open the ring skeleton, and (iv) hydrosilylation of the terminal olefin. The present borane catalysis also works efficiently for the C-N bond cleavage of acyclic tertiary amines. On the basis of experimental and computational studies, the silicon atom was elucidated to play a pivotal role in the β-amino elimination step.

Application of nano-carbon supported monatomic palladium-based catalyst in catalytic hydrogenation of nitrile compound to prepare secondary amine

The invention discloses application of a nano-carbon supported monatomic palladium-based catalyst in catalytic hydrogenation of a nitrile compound to prepare a secondary amine and belongs to the technical field of catalysts with application of catalytic hydrogenation of liquid-phase nitrile compounds. By adopting the monatomically dispersed palladium-based catalyst, a corresponding secondary aminecompound is generated with high selectivity under a mild condition, and the catalysis reaction conditions are that the reaction temperature is 45-90 DEG C and ammonia borane is adopted as a hydrogensource. In the catalyst disclosed by the invention, metals exist in a monatomic dispersion state, so that the utilization efficiency of the metals can be effectively improved, and the activity and theselectivity of the nitrile compound can be remarkably improved. In addition, the monatomically dispersed catalyst is convenient to prepare and low in cost, and has very good application prospects incatalytic hydrogenation of the nitrile compound to prepare the secondary amine.

Method for preparing secondary amines through hydrogen transferring selective nitrile reduction

The invention discloses a method for preparing secondary amines through hydrogen transferring selective nitrile reduction. According to the method, nitrile compounds (including aryl nitrile derivatives, chain and cyclic aliphatic nitrile and the like) are taken as raw materials, oxazaborolidine is taken as a hydrogen transferring agent, low-price copper and ferric metal salt are taken as additivesto catalyze the nitrile compounds to perform hydrogen transferring reaction, and therefore a corresponding secondary amine product is prepared, wherein the oxazaborolidine is prepared by the reactionof amino alcohol and a tetrahydrofuran complex of borane. The method has the advantages that the reaction condition is simple and mild, a low-price copper salt is taken as a catalyst, alkali is takenas an additive, and reduction reaction can be conducted combining with the nitrile and the hydrogen transferring agent, the reduction product is the secondary amine only, the selectivity is good, theyield is high, the hydrogen transferring agent, the additive and the catalyst are low in price and easy to obtain, the method is green and environmentally friendly, the operation is safe, the reproducibility is high, and effective schemes are provided for subsequent industrial production.