783-08-4

Usage

InChI:InChI=1/C14H13NO/c1-16-14-9-7-13(8-10-14)15-11-12-5-3-2-4-6-12/h2-11H,1H3/b15-11+

Upstream product

• 100-52-7 benzaldehyde 
• 104-94-9 4-methoxy-aniline 
• 588-53-4 4-benzylidenamino-phenol 
• 77-78-1 dimethyl sulfate 
• 74-88-4 methyl iodide 
• 19064-76-7 N-benzylidene-4-methoxyaniline oxide 
• 2211-66-7 N-phenyl(methylidene)cyclohexanamine 
• 123-11-5 4-methoxy-benzaldehyde 
• 62-53-3 aniline 
• 14796-89-5 4-methoxy-N-(triphenylphosphoran-ylidene)-aniline 
• 2101-87-3 p-methoxy-phenylazide 
• 108-88-3 toluene 
• 100-51-6 benzyl alcohol 
• 26456-05-3 10-methylacridinium perchlorate 

Downstream Products

• 420133-77-3 2,3,6-trichloro-4-methoxy-aniline 
• 60566-20-3 N-(4-methoxyphenyl)-N'-(4-methoxyphenyl)benzamidine 
• 100-52-7 benzaldehyde 
• 51527-45-8 (±)-trans-1-(4-methoxyphenyl)-3,4-diphenylazetidin-2-one 
• 6709-42-8 N-(4-methoxyphenyl)-1,1-diphenylmethylamine 
• 32795-58-7 2-phenyl-6-methoxyquinoline-4-carboxylic acid 
• 116028-06-9 1-(4-methoxy-phenyl)-3,3,4-triphenyl-azetidin-2-one 
• 17377-95-6 benzyl(4-methoxyphenyl)amine 
• 6725-34-4 thiobenzaldehyde 
• 34798-63-5 3-(4-methoxy-phenyl)-5-naphthalen-2-yloxymethyl-2-phenyl-oxazolidine 
• 138495-01-9 1-(4-methoxyphenylamino)-3-methyl-1-phenylbutan-2-one 
• 77894-47-4 cis-4-hydroxy-2-(4-methoxyphenyl)-3-phenyl-3,4-dihydro-1(2H)-isoquinolone 
• 77894-47-4 trans-4-hydroxy-2-(4-methoxyphenyl)-3-phenyl-3,4-dihydro-1(2H)-isoquinolone 
• 115781-70-9 3-(p-methoxyphenyl)-2-styryl-3,4-dihydro-4-quinazolone 

Relevant academic research and scientific papers

Controlling Proton-Coupled Electron Transfer in Bioinspired Artificial Photosynthetic Relays

Bioinspired constructs consisting of benzimidazole-phenol moieties bearing N-phenylimines as proton-accepting substituents have been designed to mimic the H-bond network associated with the TyrZ-His190 redox relay in photosystem II. These compo

Cobalt-Catalyzed Deoxygenative Hydroboration of Nitro Compounds and Applications to One-Pot Synthesis of Aldimines and Amides

The commercially available and bench-stable Co(acac)2 ligated with bis[(2-diphenylphosphino)phenyl] ether (dpephos) was employed for selective room temperature hydroboration of nitro compounds with HBPin (TOF up to 4615 h?1), tolerating halide, hydroxy, amino, ether, ester, lactone, amide and heteroaromatic functionalities. These reactions offered a direct access to a variety of N-borylamines RN(H)BPin, which were in situ treated with aldehydes and carboxylic acids to produce a series of aldimines and secondary carboxamides without the need for dehydrating and/or coupling reagents. Combination of these transformations in a sequential one-pot manner allowed for direct and selective synthesis of aldimines and secondary carboxamides from readily available and inexpensive nitro compounds.

Method for preparing asymmetric imine or asymmetric secondary amine compound through photocatalysis

The invention relates to a method for preparing asymmetric imine or asymmetric secondary amine compounds through photocatalysis. According to the method, under the conditions of illumination and inert gas, different types of photocatalysts supported by cocatalysts are selected, so that an aromatic alcohol compound and an aromatic amino compound can react to obtain the asymmetric imine compound or the asymmetric secondary amine compound. The method can be used for replacing the existing mature organic synthesis process, is mild in condition and high in selectivity, has universality and is suitable for industrial production.

Azetidinimines as a novel series of non-covalent broad-spectrum inhibitors of β-lactamases with submicromolar activities against carbapenemases KPC-2 (class A), NDM-1 (class B) and OXA-48 (class D)

The occurrence of resistances in Gram negative bacteria is steadily increasing to reach extremely worrying levels and one of the main causes of resistance is the massive spread of very efficient β-lactamases which render most β-lactam antibiotics useless. Herein, we report the development of a series of imino-analogues of β-lactams (namely azetidinimines) as efficient non-covalent inhibitors of β-lactamases. Despite the structural and mechanistic differences between serine-β-lactamases KPC-2 and OXA-48 and metallo-β-lactamase NDM-1, all three enzymes can be inhibited at a submicromolar level by compound 7dfm, which can also repotentiate imipenem against a resistant strain of Escherichia coli expressing NDM-1. We show that 7dfm can efficiently inhibit not only the three main clinically-relevant carbapenemases of Ambler classes A (KPC-2), B (NDM-1) and D (OXA-48) with Ki's below 0.3 μM, but also the cephalosporinase CMY-2 (class C, 86% inhibition at 10 μM). Our results pave the way for the development of a new structurally original family of non-covalent broad-spectrum inhibitors of β-lactamases.

Integrated Flow Synthesis of α-Amino Acids byIn SituGeneration of Aldimines and Subsequent Electrochemical Carboxylation

The synthesis of α-amino acids was carried out in a continuous flow system. In this system, aldimines were efficiently generatedin situvia the dehydration-condensation of aldehydes with anilines in a desiccant bed column filled with 4 ? molecular sieves d

Au(I) Catalyzed Synthesis of Densely Substituted Pyrazolines and Dihydropyridines via Sequential Aza-Enyne Metathesis/6π-Electrocyclization

A gold(I) autotandem catalysis protocol is reported for the de novo synthesis of densely substituted pyrazolines and dihydropyridines from the corresponding imine derivatives in a highly regioselective fashion via a one-pot aza-enyne metathesis/6π-electrocyclization sequence. The substituents on the nitrogen atom of the imine perfectly control the reaction pathways from the pivotal 1-azabutadiene intermediate; thus, carbazates were converted into pyrazolines via 6π-electrocyclization of α,β-unsaturated hydrazones, while aryl imines provided dihydropyridines via 6π-electrocyclization of 3-azahexatrienes.

Efficient Imine Formation by Oxidative Coupling at Low Temperature Catalyzed by High-Surface-Area Mesoporous CeO2 with Exceptional Redox Property

High-surface-area mesoporous CeO2 (hsmCeO2) was prepared by a facile organic-template-induced homogeneous precipitation process and showed excellent catalytic activity in imine synthesis in the absence of base from primary alcohols and amines in air atmosphere at low temperature. For comparison, ordinary CeO2 and hsmCeO2 after different thermal treatments were also investigated. XRD, N2 physisorption, UV-Raman, H2 temperature-programmed reduction, O2 temperature-programmed desorption, EPR spectroscopy, and X-ray photoelectron spectroscopy were used to unravel the structural and redox properties. The hsmCeO2 calcined at 400 °C shows the highest specific surface area (158 m2 g?1), the highest fraction of surface coordinatively unsaturated Ce3+ ions (18.2 %), and the highest concentration of reactive oxygen vacancies (2.4×1015 spins g?1). In the model reaction of oxidative coupling of benzyl alcohol and aniline, such an exceptional redox property of the hsmCeO2 catalyst can boost benzylideneaniline formation (2.75 and 5.55 mmol (Formula presented.) h?1 based on >99 % yield at 60 and 80 °C, respectively) in air with no base additives. It can also work effectively at a temperature of 30 °C and in gram-scale synthesis. These are among the best results for all benchmark ceria catalysts in the literature. Moreover, the hsmCeO2 catalyst shows a wide scope towards primary alcohols and amines with good to excellent yield of imines. The influence of reaction parameters, the reusability of the catalyst, and the reaction mechanism were investigated.

Highly efficient and selective one-pot tandem imine synthesis via amine-alcohol cross-coupling reaction catalysed by chromium-based MIL-101 supported Au nanoparticles

One-pot tandem synthesis of imines from alcohols and amines is regarded as an effective, economic and green approach under mild conditions. In this work, Au nanoparticles (NPs) dispersed on MIL-101 (Au/MIL-101) were demonstrated as highly active and selective bifunctional heterogeneous catalyst for production of various imine derivatives with excellent yields, via amine-alcohol cross-coupling reaction at 343 K in an open flask under an Ar atmosphere. Various physicochemical techniques, including inductively coupled plasma optical emission spectroscopy (ICP-OES), powder X-ray diffraction (P-XRD), X-ray photoelectron spectroscopy (XPS) transmission electron microscopy (TEM) and N2 adsorption-desorption, were used to characterize of the Au/MIL-101 catalyst. The obtained bifunctional catalyst is highly active and selective towards one-pot imine formation and exhibited the highest TOF (30.15-51.47 h?1) among all the ever-reported MOF-supported Au catalysts. The reaction mechanism of the imine formation from alcohol and amine over Au/MIL-101 catalyst was proposed. Mechanism experiment results demonstrate that Au NPs highly effective in activating oxidation of benzyl alcohol to benzaldehyde while the Lewis acid sites on MIL-101 catalyzed the second condensation step without interfering with the oxidation step. As a result, the excellent catalytic performance of Au/MIL-101 can be ascribed to the synergistic effect between Au NPs with Lewis acid sites in MIL-101.

Functional POM-catalyst for selective oxidative dehydrogenative couplings under aerobic conditions

Development of selective and efficient reusable catalytic systems for sustainable chemical production under benign conditions is attractive and received much attention. Herein, we report a rod-shaped octadecyl trimethylammonium functionalized Keggin-type polyoxometalate [PMO12O40] hybrids (OTA-POM) as an efficient heterogeneous catalyst for selective oxidative dehydrogenative couplings under aerobic conditions without any additive or external base. The catalyst recovery and subsequent five successive recyclability studies of hybrid POM confirms the heterogeneous nature of present catalytic system.

Switchable Imine and Amine Synthesis Catalyzed by a Well-Defined Cobalt Complex

Switchable imine and amine synthesis catalyzed by a tripodal ligand-supported well-defined cobalt complex is presented herein. A large variety of primary alcohols and amines were selectively converted to imines or amines in good to excellent yields. It is discovered that the base plays a crucial role on the selectivity. A catalytic amount of base leads to the imine formation, while an excess loading of base results in the amine product. This strategy on product selectivity also strongly depends on the organometallic catalysts in use. We expect that the present study could provide useful insights toward selective organic synthesis and catalyst design.