5332-96-7

Usage

Uses

It is applied as an intermediate in organic synthesis.

InChI:InChI=1/C9H9NO3/c1-7(11)6-8-2-4-9(5-3-8)10(12)13/h2-5H,6H2,1H3

Upstream product

• 186581-53-3 diazomethane 
• 1460-05-5 p-nitrophenylacetaldehyde 
• 859056-44-3 2-acetoxy-1-(4-nitro-phenyl)-propene 
• 62088-12-4 4-(4-nitro-phenyl)-3-oxo-butyric acid ethyl ester 
• 90945-64-5 4-(4-nitrophenyl)-3-oxobutyric acid 
• 141-97-9 ethyl acetoacetate 
• 100-00-5 4-chlorobenzonitrile 
• 52287-53-3 1-nitro-4-[(1E)-2-nitro-1-propenyl]benzene 
• 100-25-4 para-dinitrobenzene 
• 67-64-1 acetone 
• 15435-71-9 sodium acetylacetonate 
• 586-78-7 para-nitrophenyl bromide 
• 105-53-3 diethyl malonate 
• 50434-36-1 4-nitrophenylacetyl chloride 

Downstream Products

• 27683-80-3 2-chloro-3-(4-nitro-phenyl)-propene 
• 80605-38-5 1-(p-nitrophenyl)-2-propanone oxime 
• 144380-89-2 1-Methyl-2-(4-nitro-phenyl)-ethylideneamine 
• 89185-83-1 3-(4-nitrophenyl)-pentane-2,4-dione 
• 85345-02-4 (p-nitrophenyl)acetone ethylene glycol ketal 
• 58949-75-0 4-(2-oxopropyl)benzonitrile 
• 185557-09-9 5-hydroxy-5-methyl-4-(4-nitrophenyl)furan-2(5H)-one 
• 860519-10-4 2-chloro-1-(4-nitro-phenyl)-propene 
• 174072-89-0 2-Amino-4-methyl-5-(4-nitrophenyl)thiophene-3-carboxylic acid ethyl ester 
• 868363-14-8 2-{[(Z)-1-Methyl-2-(4-nitro-phenyl)-vinylamino]-methylene}-malonic acid diethyl ester 
• 481049-95-0 N-(4-{5-{[benzyl(methyl)amino]methyl}-1-(2,6-difluorobenzyl)-3-phenyl-2,4-dioxo-1,2,3,4-tetrahydrothieno[2,3-d]pyrimidin-6-yl}phenyl)-N'-ethylurea 

Relevant academic research and scientific papers

Markovnikov Wacker-Tsuji Oxidation of Allyl(hetero)arenes and Application in a One-Pot Photo-Metal-Biocatalytic Approach to Enantioenriched Amines and Alcohols

The Wacker-Tsuji aerobic oxidation of various allyl(hetero)arenes under photocatalytic conditions to form the corresponding methyl ketones is presented. By using a palladium complex [PdCl2(MeCN)2] and the photosensitizer [Acr-Mes]ClO4 in aqueous medium and at room temperature, and by simple irradiation with blue led light, the desired carbonyl compounds were synthesized with high conversions (>80%) and excellent selectivities (>90%). The key process was the transient formation of Pd nanoparticles that can activate oxygen, thus recycling the Pd(II) species necessary in the Wacker oxidative reaction. While light irradiation was strictly mandatory, the addition of the photocatalyst improved the reaction selectivity, due to the formation of the starting allyl(hetero)arene from some of the obtained by-products, thus entering back in the Wacker-Tsuji catalytic cycle. Once optimized, the oxidation reaction was combined in a one-pot two-step sequential protocol with an enzymatic transformation. Depending on the biocatalyst employed, i. e. an amine transaminase or an alcohol dehydrogenase, the corresponding (R)- and (S)-1-arylpropan-2-amines or 1-arylpropan-2-ols, respectively, could be synthesized in most cases with high yields (>70%) and in enantiopure form. Finally, an application of this photo-metal-biocatalytic strategy has been demonstrated in order to get access in a straightforward manner to selegiline, an anti-Parkinson drug. (Figure presented.).

Aryl C-F bond functionalization preparation method

The invention relates to the technical field of organic compound synthesis, in particular to an aryl C-F bond functionalization preparation method. A fluorobenzene compound and a nucleophilic reagent react under the action of a composite catalyst, wherein the composite catalyst is formed by mixing a visible light catalyst and a metal catalyst. The photocatalyst is adopted, the reaction process is safe and controllable, and operation in the preparation and production process is simplified; a purple LED is used as a reaction energy source and is green and environment-friendly, the energy utilization rate is high, and conversion from light energy to chemical energy can be efficiently realized; in the reaction, a simple nucleophilic reagent is used for attacking free radical cation species generated under a visible light catalysis condition, so that a target product with an extremely wide range is efficiently and greenly prepared; the operation steps are simplified, and the reaction route is shortened; and moreover, the forward reaction rate is high, and the production efficiency is remarkably improved.

Asymmetric Catalytic Epoxidation of Terminal Enones for the Synthesis of Triazole Antifungal Agents

An enantioselective epoxidation of α-substituted vinyl ketones was realized to construct the key epoxide intermediates for the synthesis of various triazole antifungal agents. The reaction proceeded efficiently in high yields with good enantioselectivities by employing a chiral N,N′-dioxide/ScIII complex as the chiral catalyst and 35% aq. H2O2 as the oxidant. It enabled the facile transformation for optically active isavuconazole, efinaconazole, and other potential antifungal agents.

UiO-66 microcrystals catalyzed direct arylation of enol acetates and heteroarenes with aryl diazonium salts in water

UiO-66 is a classic Metal–organic framework (MOF) that constructed by zirconium cations and terephthalate with high chemical and thermal stability. Using pristine UiO-66 nanocrystals as the catalysts, the carbon–carbon bond formation based on denitrogenat

Preparation method of Rugolix key intermediate

The invention relates to a preparation method of a Rugolix key intermediate. 4-nitrophenyl acetic acid is used as a raw material, and a target product is obtained through four steps of reaction. The preparation method avoids the use of toxic reagents and has the advantages of mild reaction conditions, low cost, high yield and simple route and is suitable for industrial large-scale production.

Iron powder and tin/tin chloride as new reducing agents of Meerwein arylation reaction with unexpected recycling to anilines

Simple and rapid route for Meerwein arylation reaction using iron powder or a mixture of tin/tin chloride has been developed. In the presence of iron powder, different aryl diazonium salts reacted with methyl vinyl ketone, acrylates, and isopropenyl acetate. Production of oximes was detected as the main product with acrylates or in a mixture with β-aryl methyl ketones in the case of methyl vinyl ketone. The in situ produced HNO2 from an excess of NaNO2/HCl was trapped by alkyl aryl radical to form oximes in the E configuration form. The presence of tin/tin chloride mixture in the reaction of the aryl diazonium salts with methyl vinyl ketone produced Michael products along with β-aryl methyl ketones. The predicted α-aryl methyl ketones from the reaction of isopropenyl acetate with the diazotized anilines were obtained using iron or tin/tin chloride mixture.

1-aryl-2-acetone compound preparation method

The invention discloses a 1-aryl-2-acetone compound preparation method, which comprises: (1) carrying out a reaction on (E)-2-methyl-3-aryl acrylic acid (I) as a starting raw material and diphenyl azidophosphate (DPPPA) in the presence of an organic alkali; (2) carrying out a heating reaction; and (3) adding an acidic aqueous solution into the reaction solution, and carrying out a reaction to obtain the 1-aryl-2-acetone compound with a structural formula (IV). According to the present invention, the method can solve the technical problems of difficultly available, highly-corrosive, highly toxic and highly explosive reagents, long steps, low yield, tedious operation and the like in the 1-aryl-2-acetone synthesis in the prior art, has characteristics of easily available raw materials, safe and simple operation, mild condition and high yield, and is suitable for industrial production.

Porphyrins as Photoredox Catalysts in Csp2-H Arylations: Batch and Continuous Flow Approaches

We have investigated both batch and continuous flow photoarylations of enol-acetates to yield different α-arylated aldehyde and ketone building blocks by using diazonium salts as the aryl-radical source. Different porphyrins were used as SET photocatalysts, and photophysical as well as electrochemical studies were performed to rationalize the photoredox properties and suggest mechanistic insights. Notably, the most electron-deficient porphyrin (meso-tetra(pentafluorophenyl)porphyrin) shows the best photoactivity as an electron donor in the triplet excited state, which was rationalized by the redox potentials of excited states and the turnover of the porphyrins in the photocatalytic cycle. A two-step continuous protocol and multigram-scale reactions are also presented revealing a robust, cost-competitive, and easy methodology, highlighting the significant potential of porphyrins as SET photocatalysts.

Salicylic Acid-Catalyzed Arylation of Enol Acetates with Anilines

α-Aryl ketones are both structure moieties commonly found in bioactive compounds and versatile synthetic intermediates for the preparation of drug-like molecules. An operationally simple and scalable protocol has been developed to prepare α-aryl ketones from readily available aromatic amines and enol acetates (or silyl enol ethers). This metal-free methodology features the use of salicylic acid as a convenient catalyst to promote the formation of aryl radicals from in-situ generated aryl diazonium salts, without demanding thermal or photochemical activation. The mild reaction conditions used are compatible with anilines substituted with diverse functionalities. Structural elaboration of some prepared α-aryl ketones was accomplished to illustrate their usefulness as building blocks. (Figure presented.).

Merging visible-light photoredox and micellar catalysis: Arylation reactions with anilines nitrosated in situ

An aqueous photocatalytic system was designed by merging visible-light photoredox catalysis with micellar catalysis. Eosin B, an organic dye, was utilized as the photocatalyst, and Triton X-100 was employed as the surfactant; both are inexpensive and commercially available. This clean and energy-saving catalytic system enables photocatalytic reactions of the diazonium ion generated in situ to proceed smoothly in water without any co-solvents or additives at room temperature.