14428-98-9

Usage

Aromatic amine derivative

1-phenyl-N-[(1E)-1-phenylethylidene]methanamine belongs to the class of aromatic amines, which are derivatives containing an amine functional group (-NH2) and an aromatic ring in their structure.

Phenyl group attached to nitrogen atom

A phenyl group (a ring of six carbon atoms with alternating single and double bonds) is directly attached to the nitrogen atom in 1-phenyl-N-[(1E)-1-phenylethylidene]methanamine.

Ethylidene substituent

The compound contains an ethylidene group (-CH=) as a substituent, which is a vinyl group without the hydrogen atom.

Another phenyl group in the ethylidene substituent

The ethylidene group in the compound is attached to another phenyl group, forming a (1E)-1-phenylethylidene structure.

Potential applications in organic synthesis

1-phenyl-N-[(1E)-1-phenylethylidene]methanamine can be used as a reagent in the production of other organic compounds, making it valuable in the field of organic synthesis.

Possible uses in pharmaceutical research

Although not extensively studied, this complex chemical compound may have potential applications in pharmaceutical research due to its unique structure and properties.

Complex chemical compound

1-phenyl-N-[(1E)-1-phenylethylidene]methanamine is a complex chemical compound with a variety of functional groups and structures, which may contribute to its potential industrial and research applications.

Upstream product

• 123-91-1 1,4-dioxane 
• 64-17-5 ethanol 
• 3129-98-4 (R)-benzylidene-(1-phenylethyl)amine 
• 141-52-6 sodium ethanolate 
• 17480-71-6 N-benzylidene-α-methylbenzylamine 
• 98-86-2 acetophenone 
• 100-46-9 benzylamine 
• 536-74-3 phenylacetylene 
• 1430962-42-7 acetophenone N,N-(benzyl(pent-4-en-1-yl)carbamoyl) oxime 
• 98-85-1 1-Phenylethanol 
• 614-47-1 1,3-diphenyl-propen-3-one 
• 622-79-7 benzyl azide 
• 100-52-7 benzaldehyde 
• 618-36-0 rac-methylbenzylamine 

Downstream Products

• 580-35-8 2,4,6-triphenylpyridine 
• 103-49-1 dibenzylamine 
• 3193-62-2 N-benzyl-1-phenylethylamine 
• 68099-99-0 2-phenyl-4-(1-phenylethylidene)oxazol-5(4H)-one 
• 56249-47-9 2-(benzylamino)-2-phenylpropanenitrile 
• 108762-73-8 N-Benzyl-N-(1-phenyl-vinyl)-benzamide 
• 108762-77-2 N-Benzyl-4-chloro-N-(1-phenyl-vinyl)-benzamide 
• 123638-32-4 N-(1-methyl-1-phenyl-3-butenyl)benzylamine 
• 6624-04-0 2-benzyl-1,3-diphenyl-propan-1-one 
• 88875-54-1 1-benzyl-4-hydroxy-5-imino-4-(4-nitrophenyl)-2-phenyl-4,5-dihydropyrrole 
• 144782-49-0 Benzyl-[1-phenyl-2-((R)-toluene-4-sulfinyl)-eth-(E)-ylidene]-amine 
• 17480-69-2 (S)-N-benzyl-1-phenylethylamine 
• 38235-77-7 (R)-N-benzyl-1-phenylethylamine 
• 17480-71-6 N-benzylidene-α-methylbenzylamine 

Relevant academic research and scientific papers

Rh(I)-catalyzed solvent-free ortho-alkylation of aromatic imines under microwave irradiation

The synthesis of ortho-alkylated ketones through a chelation-assisted Rh (I) catalyzed ortho-alkylation reaction of aromatic imines under microwave activated solvent-free conditions in monomode reactors was performed. These conditions have been also applied to hydroacylation and ortho-alkylation reactions with aldimines.

Base-Catalyzed [3 + 2] Cycloaddition of N-Benzyl Ketimines to Arylacetylenes Followed by Oxidation: A One-Pot Access to Polyarylated 2 H-Pyrroles via Intermediate Pyrrolines

N-Benzyl ketimines undergo [3 + 2] cycloaddition with arylacetylenes in the KOBut/DMSO solution to 2,3,5-triarylpyrrolines, which are oxidized (chloranil, DDQ) in situ to 2,3,5-triaryl-2H-pyrroles in 53-71% yields. The intermediate 1-pyrrolines can be isolated in 31-91% yields and separately oxidized to the corresponding 2H-pyrroles.

Redox-Neutral Imination of Alcohol with Azide: A Sustainable Alternative to the Staudinger/Aza-Wittig Reaction

The traditional Staudinger/aza-Wittig reaction represents one of the most powerful tools for imine formation. However, for this multistep procedure, the sacrificial phosphine has to be used, resulting in difficulties in the purification process and waste disposal at the same time. Here, we report a redox-neutral azide-alcohol imination methodology enabled by a base-metal nickel PN3 pincer catalyst. The one-step, waste-free, and high atom-economical features highlight its advantages further. Moreover, mechanistic insight suggests a non-metal-ligand cooperation pathway based on the observation of an intermediate and density functional theory calculations.

Enantioselective reduction of: N -alkyl ketimines with frustrated Lewis pair catalysis using chiral borenium ions

Enantioselective reduction of ketimines was demonstrated using chiral N-heterocyclic carbene (NHC)-stabilised borenium ions in frustrated Lewis pair catalysis. High levels of enantioselectivity were achieved for substrates featuring secondary N-alkyl substituents. Comparative reactivity and mechanistic studies identify key determinants required to achieve useful enantioselectivity and represent a step forward in the further development of enantioselective FLP methodologies.

Merrifield resin-supported quinone as an efficient biomimetic catalyst for metal-free, base-free, chemoselective synthesis of 2,4,6-trisubstituted pyridines

Metal-free, base-free, biomimetic and chemoselective synthesis of 2,4,6-trisubstituted pyridines was developed under mild conditions for the first time. The heterogeneous biomimetic catalyst-recoverable Merrifield resin-supported quinone-was fully characterized by Fourier transform infrared spectroscopy (FT-IR), X-ray photoelectron spectrometry (XPS) and energy dispersive X-ray spectroscopy (EDX). This supported quinone catalyst exhibited excellent catalytic reactivity for chemoselective synthesis of 2,4,6-trisubstituted pyridines, providing an efficient and green method for the synthesis of pyridine derivatives under mild conditions. Mechanistic investigations were conducted to gain insights into the heterogeneous biomimetic catalyst as well as the resulting transformation. The successful capture of intermediates offered direct and clear evidence for the proposed mechanism.

Au nanoparticle-immobilized L-cysteine-paired porous ionic copolymer as an efficient catalyst for additive-free oxidative coupling of alcohols and amines

Herein, an L-cysteine-paired ionic copolymer (DVB-[MimLcy]n) with mesoporosity was prepared by free radical copolymerization of divinylbenzene (DVB) and imidazolium ionic liquids (ILs), followed by anion-exchange with L-cysteine. Because of the rich functional groups of –NH2, –SH, and –COO– and the porous framework, the DVB-[MimLcy]3 was revealed to be an ideal stabilizer for metal nanoparticles (NPs). Highly uniform dispersed small Au NPs (2–3 nm) immobilized on DVB-[MimLcy]3 (Aua/DVB-[MimLcy]3) can act as an efficient heterogeneous catalyst for additive-free synthesis of imines through coupling of a broad range of alcohols and organic amines and can be easily recovered and steadily reused several times.

New synthetic access to 3-fluoroalkyl-5-pyrazolecarboxylates and carboxylic acids

A novel process for preparing 3-fluoroalkyl-5-pyrazolecarboxylates and carboxylic acids is hereby presented. Easily accesible α-fluorinated ketimines were condensed with oxalyl monochloride derivatives, and the obtained vinamides underwent acid-catalyzed cyclization with substituted hydrazines. This highly efficient protocol can also be used for non-fluorinated C-3 and C-5 substituents.

Efficient Synthesis of Amines by Iron-Catalyzed C=N Transfer Hydrogenation and C=O Reductive Amination

Here we report the catalytic transfer hydrogenation (CTH) of non-activated imines promoted by a Fe-catalyst in the absence of Lewis acid co-catalysts. Use of the (cyclopentadienone)iron complex 1, which is much more active than the classical ‘Kn?lker complex’ 2, allowed to reduce a number of N-aryl and N-alkyl imines in very good yields using iPrOH as hydrogen source. The reaction proceeds with relatively low catalyst loading (0.5–2 mol%) and, remarkably, its scope includes also ketimines, whose reduction with a Fe-complex as the only catalyst has little precedents. Based on this methodology, we developed a one-pot CTH protocol for the reductive amination of aldehydes/ketones, which provides access to secondary amines in high yield without the need to isolate imine intermediates. (Figure presented.).

Asymmetric transfer hydrogenation reactions of: N -sulfonylimines by using alcohols as hydrogen sources

A palladium/zinc co-catalytic system was established and successfully utilized in the asymmetric transfer hydrogenation reactions of N-sulfonylimines with alcohols as hydrogen sources. Simple alcohols such as methanol, ethanol and benzyl alcohols are all

P-N Cooperative Borane Activation and Catalytic Hydroboration by a Distorted Phosphorous Triamide Platform

Studies of the stoichiometric and catalytic reactivity of a geometrically constrained phosphorous triamide 1 with pinacolborane (HBpin) are reported. The addition of HBpin to phosphorous triamide 1 results in cleavage of the B-H bond of pinacolborane through addition across the electrophilic phosphorus and nucleophilic N-methylanilide sites in a cooperative fashion. The kinetics of this process of were investigated by NMR spectroscopy, with the determined overall second-order empirical rate law given by ν = -k[1][HBpin], where k = 4.76 × 10-5 M-1 s-1 at 25 °C. The B-H bond activation process produces P-hydrido-1,3,2-diazaphospholene intermediate 2, which exhibits hydridic reactivity capable of reacting with imines to give phosphorous triamide intermediates, as confirmed by independent synthesis. These phosphorous triamide intermediates are typically short lived, evolving with elimination of the N-borylamine product of imine hydroboration with regeneration of the deformed phosphorous triamide 1. The kinetics of this latter process are shown to be first-order, indicative of a unimolecular mechanism. Consequently, catalytic hydroboration of a variety of imine substrates can be realized with 1 as the catalyst and HBpin as the terminal reagent. A mechanistic proposal implicating a P-N cooperative mechanism for catalysis that incorporates the various independently verified stoichiometric steps is presented, and a comparison to related phosphorus-based systems is offered.