19865-58-8

Usage

InChI:InChI=1/C13H10ClNO/c14-12-6-8-13(9-7-12)15(16)10-11-4-2-1-3-5-11/h1-10H

Upstream product

• 100-42-5 styrene 
• 932-98-9 1-chloro-4-nitroso-benzene 
• 100-52-7 benzaldehyde 
• 823-86-9 N-(4-chlorophenyl)hydroxylamine 
• 2948-37-0 N-(4-chlorophenyl)benzylamine 
• 100-00-5 4-chlorobenzonitrile 
• 98-95-3 nitrobenzene 
• 100-51-6 benzyl alcohol 
• 544-25-2 Cyclohepta-1,3,5-triene 

Downstream Products

• 55396-85-5 N,N'-bis-[2-(4-chloro-phenyl)-3,4,4-triphenyl-isoxazolidin-5-ylidene]-benzene-1,4-diamine 
• 35887-93-5 2-(4-chloro-phenyl)-3c-phenyl-(3ac,3bt,7at,7bc)-2,3,3a,3b,4,7,7a,7b-octahydro-4r,7c-etheno-benzo[3,4]cyclobuta[1,2-d]isoxazole-5,6-dicarboxylic acid dimethyl ester 
• 35887-93-5 2-(4-chloro-phenyl)-3t-phenyl-(3ac,3bt,7at,7bc)-2,3,3a,3b,4,7,7a,7b-octahydro-4r,7c-etheno-benzo[3,4]cyclobuta[1,2-d]isoxazole-5,6-dicarboxylic acid dimethyl ester 
• 117644-88-9 2-p-chlorophenyl-4-methyoxycarbonyl-3-phenyl-4-isoxazoline 
• 117644-89-0 2-p-chlorophenyl-4-ethyoxycarbonyl-3-phenyl-4-isoxazoline 
• 15110-97-1 N-benzylidene-2,4-dichloro-aniline 
• 1040389-85-2 C₂₄H₁₉ClN₂O₃ 
• 1126722-96-0 C₂₇H₂₄ClNO₅ 
• 1186503-01-4 (3S,4S)-1-(4-chlorophenyl)-3,4-diphenyl-2-azetidinone 
• 1228016-70-3 3-(4-chlorophenyl)-6,7a-di(tert-butyl)-2-phenyl-2,3,3a,7a-tetrahydro-1,2-benzisoxazole-4,5-dione 
• 1345509-82-1 ethyl 1-(4-chlorophenyl)-2,4-diphenyl-1H-imidazole-5-carboxylate 

Relevant academic research and scientific papers

α-Aryl-N-aryl nitrones: Synthesis and screening of a new scaffold for cellular protection against an oxidative toxic stimulus

Nitrone-containing compounds are commonly employed as spin traps of free radical species in chemical and biological studies. Some molecules as α-phenyl-N-t-butyl nitrone (PBN) and its derivatives have been tested as potential drugs to treat oxidative stress related diseases, as Alzheimer and stroke for example. In this work we report the design and the synthesis of α-aryl-N-aryl nitrones and their cytoprotection profile on human neuroblastoma cells (SH-SY5Y) under induced oxidative stress. All the nine synthesized nitrones showed a significant response at low micromolar concentration. The selected compound 8 (α-phenyl-N-phenyl nitrone) increased the reduced glutathione (GSH) levels by 65% and lowered the necrotic cell death from 25.8% to 3.8%. Based on our data, the designed highly conjugated nitrone double-bond skeleton can be considered as a good scaffold for further studies regarding oxidative stress-related diseases.

DFT study of 1,3-dipolar cycloadditions of C,N-disubstituted aldonitrones to chalcones evidenced by NMR and X-ray analysis

A DFT/B3LYP/6-31G*study was carried out to predict the regio- and stereoselectivities of 1,3-dipolar cycloadditions of C,N-disubstituted aldonitrones to chalcones in terms of FMO theory, DFT-based reactivity indices, and activation energy calculations. Th

Gold Catalysts Can Generate Nitrone Intermediates from a Nitrosoarene/Alkene Mixture, Enabling Two Distinct Catalytic Reactions: A Nitroso-Activated Cycloheptatriene/Benzylidene Rearrangement

Gold-catalyzed reactions of cycloheptatrienes with nitrosoarenes yield nitrone derivatives efficiently. This reaction sequence enables us to develop gold-catalyzed aerobic oxidations of cycloheptatrienes to afford benzaldehyde derivatives using CuCl and nitrosoarenes as co-catalysts (10-30 mol %). Our density functional theory calculations support a novel nitroso-activated rearrangement, tropylium → benzylidene. With the same nitrosoarenes, we developed their gold-catalyzed [2 + 2 + 1]-annulations between nitrosobenzene and two enol ethers to yield 5-alkoxyisoxazolidines using 1,4-cyclohexadienes as hydrogen donors.

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.

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.

Nitrone synthesis via pair electrochemical coupling of Nitro-Compounds with Benzyl Alcohol Derivatives

Here we report a paired electrochemical coupling of readily accessible nitro-compounds with benzyl alcohols to yield nitrone derivatives. In this work, electrochemical behavior of nitrobenzene and benzyl alcohol derivatives was studied by cyclic voltammetry and controlled potential coulommetry. Electrochemical reactions have been performed in aqueous/ethanol (or acetonitrile) solutions by employing common graphite electrodes and a simple controlled current protocol which can make this strategy more appealing than other conventional pathways.

Synthesis of Exclusively 4-Substituted β-Lactams through the Kinugasa Reaction Utilizing Calcium Carbide

A new Kinugasa reaction protocol has been elaborated for the one-pot synthesis of 4-substituted β-lactams utilizing calcium carbide and nitrone derivatives. Calcium carbide is thereby activated by TBAF·3H2O in the presence of CuCl/NMI. The ease of synthesis and use of inexpensive chemicals provides rapid access of practical quantities of β-lactams exclusively substituted at position 4.

Catalytic Transformations of Alkynes into either α-Alkoxy or α-Aryl Enolates: Mannich Reactions by Cooperative Catalysis and Evidence for Nucleophile-Directed Chemoselectivity

The catalytic formation of gold enolates from alkynes, nitrones, and nucleophiles is described, and their Mannich reactions result in nucleophile-directed chemoselectivity through cooperative catalysis. For 1-alkyn-4-ols and 2-ethynylphenols, their gold-catalyzed nitrone oxidations afforded N-containing dihydrofuran-3(2H)-ones with syn selectivity. The mechanism involves the Mannich reactions of gold enolates with imines through an O-H-N hydrogen-bonding motif. For aryloxyethynes, their gold enolates react selectively with nitrones to deliver 3-alkylidenebenzofuran-2-ones, as controlled by a C-H-O hydrogen-bonding motif.

Preparation method of 2-amino-5-halogen phenol compounds

The invention relates to a preparation method of 2-amino-5-halogen phenol compounds. The compounds are very important intermediates in fine chemistry. Due to the ortho-position special relation of a hydroxyl group in an amino group, the compounds are important raw materials for preparing heterocyclic compounds such as the benzoxazolone compound and the benzothiazolone compound which are intermediates with the important value in medical drugs. The 2-amino-5-halogen phenol compounds can serve as anti-cancer drugs such as hydroxamic acid anti-cancer drugs and intermediates of dye and have wide application in chemical engineering, soft matter, materials and the like. According to the method, nitrone is taken as a raw material and easily prepared from a halogen nitrobenzene compound; raw materials of the halogen nitrobenzene compound are low in cost and wide in source.