100485-58-3

Usage

General Description

1(2H)-Naphthalenone, 3,4-dihydro-, oxime, (Z)- is a chemical compound also known as Norfluoxetine oxime. It is an oxime derivative of fluoxetine, which is a selective serotonin reuptake inhibitor (SSRI) used in the treatment of depression, obsessive-compulsive disorder, bulimia nervosa, and panic disorder. The oxime form of fluoxetine is believed to have similar pharmacological effects as the parent compound, potentially acting as an antidepressant and anxiolytic. It is primarily used as a research tool to study the pharmacological and toxicological properties of fluoxetine and its derivatives. 1(2H)-Naphthalenone, 3,4-dihydro-, oxime, (Z)- has the potential for medicinal use in treating mental health disorders and may have applications in the field of neuroscience research.

Upstream product

• 119-64-2 tetralin 
• 56826-69-8 5,6,7,8-tetrahydro-8-quinolinone 
• 529-34-0 3,4-dihydronaphthalene-1(2H)-one 
• 771-29-9 1,2,3,4-tetrahydro-1-naphthyl hydroperoxide 
• 2217-40-5 1,2,3,4-tetrahydronaphthalen-1-amine 
• 447-53-0 1,2-Dihydronaphthalene 

Downstream Products

• 575-36-0 1-acetamidonaphthalene 
• 134-32-7 1-amino-naphthalene 
• 81963-68-0 4,5-Dihydro-3-(2-hydroxyphenyl)napth<1,2-c>isoxazole 
• 56384-68-0 3,4-Dihydro-2H-naphthalen-1-one O-trityl-oxime 
• 213272-97-0 N-(3,4-dihydro-1-naphthyl)acetamide 
• 2217-40-5 1,2,3,4-tetrahydronaphthalen-1-amine 
• 192461-79-3 N-[(1E)-3,4-dihydronaphthalen-1(2H)-ylidene]-P,P-diphenylphosphinic amide 
• 138711-03-2 3,4-Dihydro-2H-naphthalen-1-one O-[3-(ethyl-phenyl-amino)-2-hydroxy-propyl]-oxime 
• 138711-15-6 1-<3-(N-phenylpiperazinylpropyloximino)>tetralin 
• 138711-01-0 3,4-Dihydro-2H-naphthalen-1-one O-[2-hydroxy-3-(4-phenyl-piperazin-1-yl)-propyl]-oxime 
• 1198575-55-1 2,3-diphenyl-8,9-dihydro-7H-benzo[de]quinoline 
• 1236106-52-7 (4-methoxyphenyl)(1-thioxo-1,4-dihydronaphthalen-2-yl)phosphinodithioic acid 
• 1236106-54-9 3,4-dihydro-N-mercaptonaphthalen-1(2H)-imine 
• 1236106-55-0 C₂₀H₂₂N₂S₂ 

Relevant academic research and scientific papers

One-pot synthesis of pyrroles from ketones, hydroxylamine, and 1,2-dibromoethane in the system KOH-DMSO

Dibutyl ketone, cyclohexanone, acetophenone, α-tetralone, and methyl 2-thienyl ketone were converted into the corresponding 2,3-substituted pyrroles by reaction with hydroxylamine hydrochloride and 1,2-dibromoethane in the system KOH-DMSO.

Phenyl Benzenesulfonylhydrazides Exhibit Selective Indoleamine 2,3-Dioxygenase Inhibition with Potent in Vivo Pharmacodynamic Activity and Antitumor Efficacy

Tryptophan metabolism has been recognized as an important mechanism in immune tolerance. Indoleamine 2,3-dioxygenase plays a key role in local tryptophan metabolism via the kynurenine pathway and has emerged as a therapeutic target for cancer immunotherapy. Our prior study identified phenyl benzenesulfonyl hydrazide 2 as a potent in vitro (though not in vivo) inhibitor of indoleamine 2,3-dioxygenase. Further lead optimization to improve in vitro potencies and pharmacokinetic profiles resulted in N′-(4-bromophenyl)-2-oxo-2,3-dihydro-1H-indole-5-sulfonyl hydrazide 40, which demonstrated 59% oral bioavailability and 73% of tumor growth delay without apparent body weight loss in the murine CT26 syngeneic model, after oral administration of 400 mg/kg. Accordingly, 40, is proposed as a potential drug lead worthy of advanced preclinical evaluation.

Selective Catalytic Oxidation of Benzylic and Allylic Amines to Oximes with H2O2 over TS-1

Catalytic system of TS-1-H2O2 combination has been shown to display remarkable reaction selectivity in the oxidation of benzylic and allylic amines to oximes in excellent yields.

Rhodium/MonoPhos-Catalysed Asymmetric Hydrogenation of Enamides

The monodentate phosphoramidite MonoPhos has been used in the rhodium-catalysed asymmetric hydrogenation of N-acetyl-α-arylenamides. This ligand is readily available via a one-step procedure and is air stable. Its Rh(I) complex, which is an effective catalyst precursor for the hydrogenation of dehydroamino acids, also gives high enantioselectivities for this class of substrates. Because of the facile synthesis and stability of MonoPhos, its complex provides a general solution in preparing chiral amine derivatives through asymmetric hydrogenation.

Direct oxidative coupling of enamides and 1,3-dicarbonyl compounds: A facile and versatile approach to dihydrofurans, furans, pyrroles, and dicarbonyl enamides

An efficient manganese(III)-mediated oxidative coupling reaction between α-aryl enamides and 1,3-dicarbonyl compounds has been developed. A series of dihydrofurans and dicarbonyl enamides were synthesized in moderate to good yields. Moreover, these dihydrofurans could be readily transformed into the corresponding furans and pyrroles via the Paal-Knorr reaction.

Synthesis of tetrahydronaphthyl thioureas as potent appetite suppressants

A series of thiourea derivatives (7-23, 25-27) of 1- aminotetrahydronaphthalene (4) and 1-amino-2-hydroxytetrahydronaphthalene (5) were synthesized in single pot in 48-90% yield and evaluated for their anorexigenic activity. Among them compounds 10, 14, 15, 16 and 22 exhibited significant anorexigenic activity without any antidepressant effect and provided a new structural lead for appetite suppressants.

Chasing the agostic interaction in ligand assisted cyclometallation reactions of palladium(II)

A 500 MHz NMR study of the reaction between 1-tetralone oxime and PdCl42- in CD3OD shows resonances attributable to a potential agostic intermediate prior to the formation of the insoluble cyclopalladated product which itself was characterised by X-ray crystallography. Calculated structural, spectroscopic, QTAIM, NBO and NCI analysis results obtained from density functional theory (DFT) calculations give a full description of the putative agostic intermediate [PdCl2(1-tetralone oxime)] (1) which is shown to include a previously unrecognised π-electron density donation from the aromatic ring to the metal in close proximity to the agostic carbon atom. Changing the (N)-OH donor to (N)-OMe does not effect the magnitude of these interactions. (N)-OH and (N)-OMe acetophenone imines in which the aromatic ring has the potential to rotate show similar agostic and π-electron donation to the alicyclic ring counterparts. 1-Tetralone which coordinates to the metal by a Pd-O bond that is much weaker than the Pd-N complexes has a slightly stronger agostic component and slightly weaker π-electron donation than the oxime counterpart.

Access to pyrrolo[2,1-: A] isoindolediones from oxime acetates and ninhydrin via Cu(i)-mediated domino annulations

A copper-mediated domino condensation reaction of readily accessible oxime acetates with ninhydrin is reported to afford pyrrolo[2,1-a]isoindolediones via new C-C & C-N bond formations. A wide range of oxime acetates were shown to generally participate in the reaction to produce the condensed products in excellent yields. The necessary control experiments were performed and the mechanism is proposed to involve sequentially the formation of iminium radical via Cu-mediated N-O bond cleavage of oxime acetates, addition of the radical to ninhydrin and rearrangement via ring expansion.

Beckmann rearrangement of ketoximes promoted by cyanuric chloride and dimethyl sulfoxide under a mild condition

Synthesis of amides via Beckmann rearrangement of ketoximes promoted by cyanuric chloride (TCT)/DMSO under mild conditions has been reported. Conditions of the Beckmann rearrangement, e.g., solvents, the ratios of TCT/DMSO, and the temperature, were investigated using diphenylmethanone oxime as a substrate. The optimized conditions were adopted to afford fourteen amides with yields ranging from 20% to 99%. A plausible mechanism involving an active dimethyl alkoxysulfonium intermediate was proposed according to the mass spectrometry analysis. To our best knowledge, this is the first case of study on Beckmann rearrangement of ketoximes promoted by TCT/DMSO under a mild condition to afford amides efficiently.

Rhodium(iii)-catalyzed asymmetric [4+1] spiroannulations of: O -pivaloyl oximes with α-diazo compounds

Chiral RhIII catalysts can catalyze the asymmetric [4+1] spiroannulation of O-pivaloyl oximes with α-diazo homophthalimides under redox-neutral and acid/base-neutral conditions, leading to formation of chiral spirocyclic imines as a result of C-H activation and N-O cleavage. The reaction proceeded with high efficiency and features broad substrate scope, mild reaction conditions, and high to excellent enantioselectivities. This journal is