3240-95-7

Usage

Uses

Used in Flavor Industry:
N-Benzylidene-2-phenylethanamine is used as a flavor ingredient for enhancing the taste and aroma of products in the flavor industry. It is particularly utilized in the processing of fermented dairy streams, where it contributes to the development of desirable flavors and fragrances.
Used in Pharmaceutical Industry:
Although not explicitly mentioned in the provided materials, N-Benzylidene-2-phenylethanamine and its derivatives may also hold potential applications in the pharmaceutical industry. Given their chemical structure, these compounds could be explored for their possible roles in drug development, targeting specific biological pathways or receptors.

Upstream product

• 75780-68-6 N-benzylidene-β-(2-bromophenyl)ethylamin 
• 64-04-0 phenethylamine 
• 3647-71-0 N-benzyl-2-phenylethylamine 
• 100-51-6 benzyl alcohol 
• 63-91-2 L-phenylalanine 
• 100-52-7 benzaldehyde 
• 100-46-9 benzylamine 
• 20989-17-7 Phenylglycinol 
• 6926-44-9 phenethyl azide 
• 6125-24-2 2-Phenylnitroethane 
• 100-47-0 benzonitrile 
• 102-96-5 (2-nitroethenyl)benzene 
• 13665-04-8 2,2-dibromoacetophenone 
• 103-63-9 1-phenyl-2-bromoethane 

Downstream Products

• 22002-68-2 N-ethyl-2-phenylethanamine 
• 589-08-2 N-Methyl-N-phenethylamine 
• 3647-71-0 N-benzyl-2-phenylethylamine 
• 24954-67-4 2-(p-nitrophenyl)ethylamine 
• 103276-50-2 N,N'-diphenethyl-bibenzyl-α,α'-diyldiamine 
• 83101-01-3 DL-N-Phenethylphenylglycinethylester 
• 632304-80-4 C₂₅H₁₉NO₃ 
• 758640-21-0 N-Benzylaniline 
• 1750-36-3 (E)-N-benzylidenebenzenamine 
• 22990-19-8 1-phenyl-1,2,3,4-tetrahydroisoquinoline 
• 66040-29-7 2-Chloracetyl-1-phenyl-1,2,3,4-tetrahydroisochinolin 

Relevant academic research and scientific papers

Anchored Palladium Complex-Generated Clusters on Zirconia: Efficiency in Reductive N-Alkylation of Amines with Carbonyl Compounds under Hydrogen Atmosphere

Carbon-nitrogen bond formation is an important method on both laboratory and industrial scales because it realizes the production of valuable pharmaceuticals, agrochemicals, and fine chemicals. Direct reductive N-alkylation of amines with carbonyl compounds via intermediary imine compounds, especially under catalytic hydrogenation conditions, is one of the most convenient, economical, and environmentally friendly methods for this process. Here we report a novel palladium species on zirconia having specific activity towards hydrogenation of imines but other carbonyl groups remaining intact. The present catalytic property offers a practical synthetic method of functionalized secondary amines by reductive N-alkylation under mild conditions with high atom-efficiency. Mechanistic studies revealed that the catalytically active species is the palladium cluster, which is generated in situ from molecular palladium complexes on the support by exposure to atmospheric hydrogen. These fundamental findings are expected to progress in developing novel cluster catalysts for chemical processes directed towards a sustainable society.

Manganese-Catalyzed Selective Hydrogenative Cross-Coupling of Nitriles and Amines to Form Secondary Imines

Manganese complexes with tridentate PNN ligands have been synthesized as catalysts for hydrogenative cross-coupling reaction of nitriles and amines to form secondary imines. This reaction afforded a variety of unsymmetrical secondary imines in good yields with excellent selectivity. Investigation of catalyst intermediates indicated that an amido manganese complex may be the active catalyst species for this reaction. (Figure presented.).

Method for synthesizing aluminum phosphate molecular sieve catalytic imine

The invention discloses a method for catalyzing synthesis of an imine by using an aluminum phosphate molecular sieve, and belongs to the technical field of catalytic synthesis of imines. Under the action of an HP-MeAlPO-5 molecular sieve, air or oxygen is used as an oxidant, and an amine and an alcohol which contain different substituents are directly subjected to oxidative coupling to synthesizethe imine under mild conditions. According to the method provided by the invention, the reaction conditions of the adopted catalytic system are mild, and the TOF is high; a reaction can efficiently catalyze the synthesis of the imine at room temperature under air; and the method can adopt transition metals, which are cheap and easy to obtain, such as iron, cobalt and nickel as a molecular sieve dopant, and the availability of the molecular sieve is improved.

Bidentate geometry-constrained iminopyridyl nickel-catalyzed synthesis of amines or imines via borrowing hydrogen or dehydrogenative condensation

The efficient Ni-catalyzed N-alkylation of various anilines with alcohols via borrowing hydrogen is reported using a bidentate geometry-constrained iminopyridyl nickel complex as the catalyst. Substituted benzylic alcohols and short/long chain aliphatic alcohols could be applied as the alkylation sources to couple with aromatic and heteroaromatic amines to give a diverse set of N-alkylation outcomes in moderate to excellent yields. The nickel catalytic system was also suitable for aliphatic amines, selectively delivering the corresponding imines via an acceptorless dehydrogenative condensation strategy.

Volatiles from the Psychrotolerant Bacterium Chryseobacterium polytrichastri

The flavobacterium Chryseobacterium polytrichastri was investigated for its volatile profile by use of a closed-loop stripping apparatus (CLSA) and subsequent GC-MS analysis. The analyses revealed a rich headspace extract with 71 identified compounds. Compound identification was based on a comparison to library mass spectra for known compounds and on a synthesis of authentic standards for unknowns. Important classes were phenylethyl amides and a series of corresponding imines and pyrroles.

CATALYTIC SYSTEMS FOR STEREOSELECTIVE SYNTHESIS OF CHIRAL AMINES BY ENANTIODIVERGENT RADICAL C-H AMINATION

In one aspect, the disclosure relates to a mode of asymmetric induction in radical processes based on sequential combination of enantiodifferentiative H-atom abstraction and stereoretentive radical substitution. Also disclosed is an asymmetric system for stereoselective synthesis of strained 5-membered cyclic sulfamides via radical 1,5-C—H amination of sulfamoyl azides. The disclosed metalloradical system can control the degree and sense of asymmetric induction in the catalytic radical C—H amination in a systematic manner. The disclosed system is applicable to a broad scope of substrates with different types of C(sp3)-H bonds and exhibits reactivity and selectivity, providing access to both enantiomers of useful 5-membered cyclic sulfamides in a highly enantioenriched form. Also disclosed are catalysts useful in these processes. This abstract is intended as a scanning tool for purposes of searching in the particular art and is not intended to be limiting of the present disclosure.

Visible light photocatalytic aerobic oxidative synthesis of imines from alcohols and amines on dye-sensitized TiO2

A general visible light photocatalytic protocol for the synthesis of imines via a two-step one-pot route on alizarin red S (ARS)-sensitized TiO2 was uncovered. This efficient synthesis protocol involves one step of the highly selective formation of aldehydes from the oxidation of alcohols with O2 on ARS-sensitized TiO2 photocatalyst, and a subsequent step of condensation of newly formed aldehydes with various amines on TiO2 to afford imines in one pot. Anatase TiO2 provides a versatile platform for catalytic amounts of ARS (0.67 mol%) to facilitate the electron transfer from dye traversing its conduction band to O2 under green LED irradiation. Moreover, the Lewis acid sites of TiO2 can promote the formation of imines from aldehydes and amines in very high isolated yields. We took advantage of both the photocatalytic and catalytic properties of TiO2 to significantly expand the scope of imines. Our work suggests that the synthetic applications of TiO2 photocatalysis can be achievable under mild conditions by exploring the excellent functionalities of TiO2.

Improving C=N bond reductions with (Cyclopentadienone)iron complexes: Scope and limitations

Herein, we broaden the application scope of (cyclo-pentadienone)iron complexes 1 in C=N bond reduction. The catalytic scope of pre-catalyst 1b, which is more active than the “Kn?lker complex” (1a) and other members of its family, has been expanded to the catalytic transfer hydrogenation (CTH) of a wider range of aldimines and ketimines, either pre-isolated or generated in situ. The kinetics of 1b-promoted CTH of ketimine S1 were assessed, showing a pseudo-first order profile, with TOF = 6.07 h–1 at 50 % conversion. Moreover, the chiral complex 1c and its analog 1d were employed in the enantioselective reduction of ketimines and reductive amination of ketones, giving fair to good yields and moderate enantioselectivity.

Asymmetric Induction and Enantiodivergence in Catalytic Radical C-H Amination via Enantiodifferentiative H-Atom Abstraction and Stereoretentive Radical Substitution

Control of enantioselectivity remains a major challenge in radical chemistry. The emergence of metalloradical catalysis (MRC) offers a conceptually new strategy for addressing this and other outstanding issues. Through the employment of D2-symmetric chiral amidoporphyrins as the supporting ligands, Co(II)-based MRC has enabled the development of new catalytic systems for asymmetric radical transformations with a unique profile of reactivity and selectivity. With the support of new-generation HuPhyrin chiral ligands whose cavity environment can be fine-tuned, the Co-centered d-radicals enable to address challenging issues that require exquisite control of fundamental radical processes. As showcased with asymmetric 1,5-C-H amination of sulfamoyl azides, the enantiocontrol of which has proven difficult, the judicious use of HuPhyrin ligand by tuning the bridge length and other remote nonchiral elements allows for controlling both the degree and sense of asymmetric induction in a systematic manner. This effort leads to successful development of new Co(II)-based catalytic systems that are highly effective for enantiodivergent radical 1,5-C-H amination, producing both enantiomers of the strained five-membered cyclic sulfamides with excellent enantioselectivities. Detailed deuterium-labeling studies, together with DFT computation, have revealed an unprecedented mode of asymmetric induction that consists of enantiodifferentiative H-atom abstraction and stereoretentive radical substitution.

Flower-like Bi2O2CO3-mediated selective oxidative coupling processes of amines under visible light irradiation

The photocatalytic selective transformation of amines is a green and cost-effective technology to obtain value-added products in chemical industry. In this work, a series of bismuth-based photocatalysts including Bi2MoO6, Bi2WO6, Bi5O7Cl, Bi5O7Br, Bi5O7I, BiPO4, BiVO4, Bi2O3 and various morphology Bi2O2CO3 (flower-like, sponge-like, plate-like and spherical)were synthesized and employed in the aerobic oxidative coupling of benzylamine. It is found that flower-like Bi2O2CO3 exhibited the highest photocatalytic activity, in which a 100% conversion of benzylamine with 99.0% selectivity of N-benzylidenebenzylamine was obtained at room temperature. Moreover, the photocatalytic oxidative coupling processes of various aromatic and aliphatic amines were further investigated, and excellent yields and selectivities of corresponding products are attained. Then, based on characterization results (XRD, SEM, BET and XPS, etc.)of catalyst, high photocatalytic activity of flower-like Bi2O2CO3 is attributed to thin nanopetals, low band gap, the morphology and large specific surface area. Finally, a possible reaction mechanism is proposed for the photocatalytic oxidative coupling of benzyl amine.