3585-93-1

Usage

Uses

Used in Pharmaceutical Industry:
N-Phenyl-4-methoxybenzylideneamine N-oxide is utilized as a catalyst in organic synthesis, specifically for the oxidation of alcohols to aldehydes or ketones. Its efficiency and versatility make it a valuable oxidizing agent in the development of pharmaceutical products.
Used in Chemical Industry:
Similarly, in the chemical industry, N-Phenyl-4-methoxybenzylideneamine N-oxide serves as a catalyst for the oxidation processes, contributing to the synthesis of various chemical compounds and intermediates. Its stable nature and ease of handling make it a preferred choice for industrial applications requiring oxidizing agents.

InChI:InChI=1/C14H13NO2/c1-17-14-9-7-12(8-10-14)11-15(16)13-5-3-2-4-6-13/h2-11H,1H3

Upstream product

• 124941-29-3 N-methoxybenzylydene-α-p-methylphenylglycine methyl ester 
• 586-96-9 Nitrosobenzene 
• 77290-54-1 N-p-methoxybenzylydene-α-phenylglycine ethyl ester 
• 98-95-3 nitrobenzene 
• 637-69-4 4-Methoxystyrene 
• 123-11-5 4-methoxy-benzaldehyde 
• 100-65-2 N-Phenylhydroxylamine 
• 156050-38-3 2-<(4-methoxyphenyl)methylsulfonyl>benzothiazole 
• 100-52-7 benzaldehyde 
• 4546-20-7 p-methoxyphenylhydroxylamine 
• 22755-09-5 N-phenyl hydroxylamine hydrochloride 
• 836-41-9 p-methoxybenzylidene-phenylamine 

Downstream Products

• 54615-68-8 (4-methoxy-phenyl)-phenylimino-acetonitrile 
• 141583-51-9 (Z)-methyl 4-methoxy-N-phenylbenzimidate 
• 29068-13-1 3-(4-methoxy-phenyl)-2-phenyl-6a-pyrrolidin-1-yl-hexahydro-cyclopenta[d]isoxazole 
• 29068-03-9 3-(4-methoxy-phenyl)-2-phenyl-7a-pyrrolidin-1-yl-octahydro-benzo[d]isoxazole 
• 52881-05-7 3-(4-methoxy-phenyl)-8b-methyl-2-phenyl-2,3,3a,8b-tetrahydro-benzo[4,5]thieno[2,3-d]isoxazole 4,4-dioxide 
• 92234-41-8 5-(1-imidazolyl)-3-(4-methoxyphenyl)-2-phenylisoxazolidine 
• 99655-20-6 5-tert-Butyl-3-(4-methoxy-phenyl)-2-phenyl-[1,4,2]oxathiazolidine 
• 123-11-5 4-methoxy-benzaldehyde 
• 133437-40-8 1-(2-(4-methoxyphenyl)-1H-indol-3-yl)ethanone 
• 133437-38-4 3-(4-methoxyphenyl)-5-methyl-2-phenyl-4-phenylsulfonyl-2,3-dihydroisoxazole 
• 21469-81-8 (2E)-3-(4-methoxyphenyl)-N,N-dimethylpropanamide 
• 1227476-15-4 Azobenzene 
• 495-48-7 azoxybenzene 
• 135386-71-9 2-Phenyl-3-(4-methoxyphenyl)-5-hydroxyisoxazolidine 

Relevant academic research and scientific papers

Optimized aqueous Kinugasa reactions for bioorthogonal chemistry applications

Kinugasa reactions hold potential for bioorthogonal chemistry in that the reagents can be biocompatible. Unlike other bioorthogonal reaction products, β-lactams are potentially reactive, which can be useful for synthesizing new biomaterials. A limiting factor for applications consists of slow reaction rates. Herein, we report an optimized aqueous copper(i)-catalyzed alkyne-nitrone cycloaddition involving rearrangement (CuANCR) with rate accelerations made possible by the use of surfactant micelles. We have investigated the factors that accelerate the aqueous CuANCR reaction and demonstrate enhanced modification of a model membrane-associated peptide. We discovered that lipids/surfactants and alkyne structure have a significant impact on the reaction rate, with biological lipids and electron-poor alkynes showing greater reactivity. These new findings have implications for the use of CuANCR for modifying integral membrane proteins as well as live cell labelling and other bioorthogonal applications.

Gold-Catalyzed Oxidative Aminocyclizations of Propargyl Alcohols and Propargyl Amines to Form Two Distinct Azacyclic Products: Carbene Formation versus a 3,3-Sigmatropic Shift of an Initial Intermediate

Gold-catalyzed oxidations of propargyl alcohols with nitrones by using a P(tBu)2(o-biphenyl)Au+ catalyst, afforded bicyclic annulation products from the Mannich reactions of gold enolates. The same reactions of propargyl amines with nitrones by using the same gold catalyst gave distinct oxoarylation products. Our DFT calculations indicate that oxidation of propargyl alcohols with nitrones by using electron-rich gold catalysts lead only to gold carbenes, which can generate gold enolates or oxoarylation intermediates with enolate species having a barrier smaller than that of oxoarylation species.

Synthesis and Antimicrobial Evaluation of New Pyrrolo-isoxazolidine Derivatives

In the present study, pyrrolo-isoxazolidines 3(a-l) and 4(a-e), 4g, 4i, 4j have been synthesized by using the 1,3-dipolar cycloaddition reactions of nitrones 1(a-l) with ester substituted N-aryl maleimide (2b). These heterocycles have been obtained in cis and trans diastereomeric forms. The structures of newly synthesized heterocycles have been confirmed from their spectroscopic parameters such as IR,1H NMR,13C NMR and ESI-MS. The in vitro antimicrobial evaluation of these compounds were also investigated. Most of the prepared heterocycles showed significant antimicrobial properties. C3-phenyl substituted products exhibited the remarkable antibacterial behaviours while C3-thienyl/furyl substituted heterocycles proved themselves potent antifungal agents.

Tandem Chiral Cu(II) Phosphate-Catalyzed Deoxygenation of Nitrones/Enantioselective Povarov Reaction with Enecarbamates

A new catalytic enantioselective tandem deoxygenation/aza-Diels-Alder reaction of nitrones with enecarbamates was serendipitously discovered in the presence of chiral copper(II) diphosphate complexes. This process affords a wide range of 4-aminotetrahydroquinolines in respectable yields under mild conditions with good to excellent ee values.

A green synthesis of nitrones in glycerol

Abstract: An eco-friendly and efficient synthesis of nitrones is presented by condensation of an equimolar amount of aldehydes and N-substituted hydroxylamine hydrochlorides in glycerol as a recyclable solvent-catalyst. This novel protocol provides rapid and mild access to a series of nitrone derivatives in good to excellent yields in the absence of catalyst and base. Graphic abstract: SYNOPSIS In this study, a base-free protocol by using glycerol as the solvent-catalyst was applied for an eco-friendly synthesis of nitrones from the condensation of aldehydes and N-substituted hydroxylaminehydrochlorides.[Figure not available: see fulltext.].

Catalytic Diastereo- and Enantioselective Synthesis of 2-Imidazolinones

Chiral cyclic ureas (2-imidazolinones) were prepared by the reaction of nitrones and isocyanoacetate esters using a multicatalytic system that combines a bifunctional Br?nsted base-squaramide organocatalyst and Ag+ as a Lewis acid. The reaction could be achieved with a range of nitrones derived from aryl- and cycloalkylaldehydes with moderate diastereo- and good enantioselectivity. A plausible mechanism involving an initial formal [3 + 3] cycloaddition of the nitrone and isocyanoacetate ester, followed by rearrangement to an aminoisocyanate and cyclization to the imidazolinone, is proposed.

Trifluoromethyl Vinyl Sulfide: A Building Block for the Synthesis of CF3S-Containing Isoxazolidines

Trifluoromethyl vinyl sulfide, a potential building block for pharmaceutically and agrochemically relevant products, is prepared and used for the first time in high-pressure-mediated 1,3-dipolar cycloaddition reactions with nitrones to synthesize (trifluoromethyl)sulfanyl isoxazolidines.

Copper-Catalyzed Synthesis of Polysubstituted Pyrroles through [3+1+1] Cycloaddition Reaction of Nitrones and Isocyanides

An efficient, copper-catalyzed [3+1+1] cycloaddition reaction was developed for the expedient synthesis of pharmacologically interesting polysubstituted pyrroles from easily available nitrones and α-acidic isocyanides. The given approach features a new mo

A Protocol to Transform Sulfones into Nitrones and Aldehydes

A simple method to transform sulfones into nitrones and therefore into the corresponding carbonyl derivatives has been developed. Some examples demonstrate that it is a new reliable and versatile reaction in the toolbox of sulfones that has great synthetic potential. NMR and computational studies were used to elucidate the mechanism.

A Protocol to Transform Sulfones into Nitrones and Aldehydes

A simple method to transform sulfones into nitrones and therefore into the corresponding carbonyl derivatives has been developed. Some examples demonstrate that it is a new reliable and versatile reaction in the toolbox of sulfones that has great synthetic potential. NMR and computational studies were used to elucidate the mechanism.