737-47-3

Usage

Uses

Used in Pharmaceutical Industry:
Cyclohexanone, 2-(a-anilinobenzyl)is used as a building block in organic synthesis for the preparation of various pharmaceuticals. Its unique structure allows it to be a key component in the development of new drugs and medicinal compounds.
Used in Polymer and Materials Science:
Cyclohexanone, 2-(a-anilinobenzyl)is also utilized in the production of polymers and other materials. Its versatility in chemical reactions enables the creation of a wide range of materials with different properties and applications.
Used in Medicinal Research:
Due to its potential biological activity, Cyclohexanone, 2-(a-anilinobenzyl)may be the subject of research for possible medicinal uses. Its exploration in this field could lead to the discovery of new therapeutic agents and treatments.

InChI:InChI=1/C19H21NO/c21-18-14-8-7-13-17(18)19(15-9-3-1-4-10-15)20-16-11-5-2-6-12-16/h1-6,9-12,17,19-20H,7-8,13-14H2

Upstream product

• 108-94-1 cyclohexanone 
• 100-52-7 benzaldehyde 
• 62-53-3 aniline 
• 538-51-2 benzylidene phenylamine 
• 1750-36-3 (E)-N-benzylidenebenzenamine 
• 5682-83-7 2-Benzylidenecyclohexanone 
• 6651-36-1 1-(Trimethylsilyloxy)cyclohexene 

Downstream Products

• 5682-83-7 (E)-2-benzylidenecyclohexanone 
• 603-34-9 N,N-diphenylaminobenzene 
• 89410-14-0 2-Chloro-3,4-diphenyl-5,6-tetramethylenetetrahydro-1,3,2-oxazaphosphorin-2-oxide 
• 164026-52-2 2-amino-4-phenyl-5,6,7,8-tetrahydro-4H-chromene-3-carbonitrile 
• 67780-13-6 2-(α-Anilinobenzyl)-1-cyclohexanol 

Relevant academic research and scientific papers

Designing a novel tetradentate polyoxometalate eco-catalyst for the synthesis of β-aminocyclohexanone derivatives in water

The synthesis of a series of known β-aminocyclohexanones has been accomplished using pentaerythrityl tetramethyl imidazolium phosphotungstate (C(MIM-PTA)4) as a new tetradentate acidic catalyst. It was prepared via condensation of pentaerythrityl tetrabromide with methyl imidazole. Then, bulky anion H2PW12O401? was substituted with Br? in the structure. This tetradentate catalyst provides designable cations and anions. Anions have two types of acids, acidic protons, and metals with Lewis acidity. In order to test the efficient catalytic behavior of the tetradentate catalyst, a controlled reaction was performed using benzaldehyde, aniline and cyclohexanone. Imine from the condensation of benzaldehyde and aniline was observed in the absence of ionic catalyst instead of desired products. Thus, this reaction would be attractive because of the time, energy, and raw material saving considerations because of the absence of isolation of intermediates and stereospecificity. The catalyst shows high catalytic activity such that after four recycles the product was obtained with high yield and purity. This reaction was performed at room temperature. Although high temperature could improve the reaction rate, it contributes to side reactions and oxidation of aldehyde and amine. The catalyst was characterized by elemental analysis, FT-IR spectroscopy, 1H NMR, 13C NMR, and TGA.

Tartaric acid-zinc nitrate as an efficient brnsted acid-assisted lewis acid catalyst for the mannich reaction

Tartaric acid-zinc nitrate has been found to be an efficient Brnsted acid-assisted Lewis acid catalytic system for the facile synthesis of β-amino carbonyl compounds through the one-pot Mannich reaction of aldehydes, aromatic amines and ketones in ethanol at room temperature. Remarkable enhancement of reactivity by tartaric acid (Br?nsted acid) was observed in these reactions in the presence of anhydrous zinc nitrate (Lewis acid), due to coordination of the tartaric acid ligand to zinc ions increasing the acidity of the system. This procedure shows some advantages such as mild reaction conditions, short reaction times and high yields.

H3PW12O40 anchored on graphene-grafted silica-coated MnFe2O4 as magnetic catalyst for Mannich reaction

In this study, a three-component nanocomposite consisted of graphene, manganese ferrite and phosphotungstic acid (PTA) has been prepared. This composite, which is designated as Graphene/MnFe2O4@PTA, was synthesized through anchoring of PTA–imidazolium ionic liquid on magnetic graphene sheets. The structural and magnetic properties of the fabricated nanocomposite were studied by employing FT-IR, SEM, EDX, TEM, ICP, VSM, P-XRD and BET techniques. The synthesized magnetic nanocomposite was examined as an efficient and recyclable acidic catalyst for Mannich reaction under solvent-free conditions. The products of this reaction, which are an important class of potentially bioactive compounds, were obtained with good to excellent yields, and the catalyst could be readily recycled without any significant loss of its activity.

H3PW12O40 supported on functionalized polyoxometalate organic-inorganic hybrid nanoparticles as efficient catalysts for three-component Mannich-type reactions in water

Two new types of catalyst were synthesized by the immobilization of H3PW12O40 (HPW12) on the surface of organic-inorganic polyoxometalate nanoparticles of H6Cu2[PPDA]6[SiW9Cu3O37]·12H2O (HybPOM) (PPDA = p-phenylenediamine) and Go/Fe3O4/HybPOM nanoparticles. These catalysts were characterized by thermogravimetric analysis (TGA), Fourier transform infrared (FT-IR) spectroscopy, scanning electron microscopy (SEM), energy dispersive X-ray analysis (EDX) and alternating gradient force magnetometry (AGFM). The IR spectroscopy as well as XRPD reveal that HPW12 were immobilized on the support. The potentiometric titration with n-butylamine reveal that the catalysts can be classified as strong acids. The results show that the particles are mostly spherical in shape and have an average size in the range of 20-50 nm. The catalytic activities of the catalysts were probed through one-pot three-component Mannich-type reactions of aldehydes, amines and ketones in water at room temperature. The catalysts were re-used at least five times without any loss of their high catalytic activity.

Bismuth Perfluoroalkylphosphinates: New Catalysts for Application in Organic Syntheses

Commercially available BiPh3was treated with perfluoroalkylphosphinic acids [for example, (C2F5)2P(O)OH] to generate novel, highly Lewis acidic bismuth(III) perfluoroalkylphosphinates of the type PhxBi[RF2PO2]3?x(x=0, 1, 2) (RF=-C2F5, -C4F9). The first bismuth(V) perfluoroalkylphosphinate, Ph3Bi[(C2F5)2PO2]2, was synthesized from Ph3BiCl2and Ag[(C2F5)2PO2]. Examples for the successful application of the catalytically active bismuth(III) and bismuth(V) phosphinates in carbon–carbon bond forming reactions, such as Friedel–Crafts acylation and alkylation, Diels–Alder, Strecker and Mannich reaction, are presented.

Br?nsted-Lewis dual acidic ionic liquid immobilized on mesoporous silica materials as an efficient cooperative catalyst for Mannich reactions

Novel mesoporous silica supported ILs have been prepared and successfully applied as a heterogeneous catalyst in Mannich reactions. The excellent recyclability of the supported catalyst, mild reaction conditions, good to excellent yields, low catalyst loading, and operational simplicity are the important features of this methodology.

Surfactant-like Br?nsted acidic ionic liquid as an efficient catalyst for selective Mannich reaction and biodiesel production in water

Abstract: The current study deals with the applications of a surfactant-like Br?nsted acidic ionic liquid (IL) 1-dodecyl-3-methylimidazolium hydrogen sulfate ([DMIm]HSO4) for Mannich reaction at room temperature. The reaction was efficiently preceded in water as solvent without using any harmful and expensive organic additives. Our findings showed that the reaction is selective for cyclohexanone and no Mannich product was observed when cyclopentanone was used as starting material. Density functional theory (DFT) calculations were performed to provide an evidence about the nature of reactivity of the cyclohexanone/cyclopentanone. The activity of the catalyst was also tested for biodiesel production of fatty acids with methanol and ethanol at mild thermal condition without applying additional water removal steps such as using additives or performing special methodologies like azeotropic distillation. In both reactions, the IL can be recycled and reused several times with relatively constant efficiency. Graphical Abstract: [Figure not available: see fulltext.]

Sulfonic acid supported on magnetic nanoparticle as an eco-friendly, durable and robust catalyst for the synthesis of β-amino carbonyl compounds through solvent free Mannich reaction

A simple, efficient and environmentally benign solid acid catalyst was prepared by anchoring a propyl sulfonic acid on the surface of silica-coated magnetic nanoparticles by low cost precursors. The catalyst has been then engaged in the efficient β-amino carbonyl compounds production via three component Mannich reaction under solvent free reaction condition at room temperature. After the completing the reaction, the catalyst was readily separated by external magnet and reused for 10 successive rounds of reaction, without any significant loss in catalytic efficiency. The solid acidic system presented reusable strategy for the efficient synthesis of β-amino carbonyl compounds, simplicity in operation, and green aspects by avoiding toxic conventional catalysts under solvent-free condition.

Different ligand titanocenes complex crystal and its preparation of β - amino carbonyl compound in the application

The invention discloses an isoligand cyclopentadiene-titanium coordination compound crystal and application thereof in preparing beta-amino carbonyl compounds. The structural formula of the cyclopentadiene-titanium coordination compound crystal is disclosed in the specification, and the cyclopentadiene-titanium coordination compound crystal is prepared from salicylic acid chelate and 3-thiophenic acid. The isoligand cyclopentadiene-titanium coordination compound crystal has the advantages of low price, no toxicity and high stability for air and water. The synthesis method has the advantages of cheap and accessible raw materials, simple and feasible synthesis steps, easy product after-treatment and high yield, and can implement gram-level preparation of the coordination compound. When being used as a cocatalyst for catalyzing the three-component Mannich reaction of cyclohexanone to prepare the beta-amino carbonyl compounds, the isoligand cyclopentadiene-titanium coordination compound crystal has the characteristics of high catalytic activity, high reaction selectivity, high product yield, no need of any solvent, simple operation process and high atom economy.