946-49-6

Usage

Uses

Used in Pharmaceutical Synthesis:
(Z)-4-(4-nitrophenyl)-3-buten-2-one is used as a key intermediate in the pharmaceutical industry for the synthesis of various drugs and medicinal compounds. Its aromatic and nitro characteristics make it a valuable building block in the development of new pharmaceuticals.
Used in Organic Chemistry:
In the field of organic chemistry, (Z)-4-(4-nitrophenyl)-3-buten-2-one is utilized as a reagent and a starting material for a range of organic reactions. Its unique structure allows for the creation of diverse chemical products, contributing to the advancement of organic chemistry research and development.
Used in Chemical Research:
(Z)-4-(4-nitrophenyl)-3-buten-2-one is also employed in chemical research as a model compound to study various reaction mechanisms and to develop new synthetic methodologies. Its properties and reactivity make it an interesting subject for scientists to explore and understand the underlying principles of chemical reactions.
Used in Chemical Education:
(Z)-4-(4-nitrophenyl)-3-buten-2-one can be used in educational settings to teach students about the properties of aromatic and nitro compounds, as well as the importance of safety measures in chemical handling. It serves as a practical example of the types of compounds encountered in the pharmaceutical and organic chemistry fields.

InChI:InChI=1/C10H9NO3/c1-8(12)2-3-9-4-6-10(7-5-9)11(13)14/h2-7H,1H3/b3-2+

Upstream product

• 88958-64-9 1-(4-nitrophenyl)-1-hydroxy-3-butanone 
• 108-24-7 acetic anhydride 
• 122-57-6 1-Phenylbut-1-en-3-one 
• 555-16-8 4-nitrobenzaldehdye 
• 67-64-1 acetone 
• 1439-36-7 1-triphenylphosphoranylidene-2-propanone 
• 24143-92-8 acetylmethylidene(triphenyl)-λ⁵-arsane 
• 7664-93-9 sulfuric acid 
• 7697-37-2 nitric acid 
• 7732-18-5 water 
• 141-97-9 ethyl acetoacetate 
• 105-45-3 acetoacetic acid methyl ester 
• 3483-11-2 lithium acetoacetate 
• 79-46-9 2-nitropropane 

Downstream Products

• 3156-41-0 1-nitro-4-(2-nitrovinyl)benzene 
• 52451-41-9 4-Ethoxy-6-(4-nitro-phenyl)-2-oxo-cyclohex-3-enecarboxylic acid ethyl ester 
• 75335-28-3 (E)-4-(4-Nitro-phenyl)-but-3-enoic acid methyl ester 
• 88958-64-9 1-(4-nitrophenyl)-1-hydroxy-3-butanone 
• 152-72-7 acenocoumarol 
• 97481-59-9 6-amino-5-(1-methyl-p-nitrocinnamylidene)-1,3-dimethyluracil 
• 97481-64-6 2-(4-nitrophenyl)-4,7,9-trimethyl-6-hydroxy-8-oxo-2,3-dihydropyrimidino<5,6-b>-1,5-diazepine 
• 90799-69-2 1-<4-Nitro-phenyl>-2-chlor-2-acetyl-aethylen 
• 64-19-7 acetic acid 
• 97039-28-6 3-(4-aminostyryl)-2-isoxazoline 
• 97039-25-3 3-(4-nitrostyryl)-2-isoxazoline 
• 97039-19-5 1-(4-nitrophenyl)-3-hydroxyimino-5-morpholino-1-pentene 

Relevant academic research and scientific papers

Organocatalytic diastereo- And enantioselective oxa-hetero-Diels-Alder reactions of enones with aryl trifluoromethyl ketones for the synthesis of trifluoromethyl-substituted tetrahydropyrans

Tetrahydropyran derivatives are found in bioactives, and introduction of the trifluoromethyl group into molecules often improves biofunctions. Here we report diastereo- and enantioselective oxa-hetero-Diels-Alder reactions catalyzed by amine-based catalyst systems that afford trifluoromethyl-substituted tetrahydropyranones. Catalyst systems and conditions suitable for the reactions to provide the desired diastereomer products with high enantioselectivities were identified, and various trifluoromethyl-substituted tetrahydropyranones were synthesized with high diastereo- and enantioselectivities. Mechanistic investigation suggested that the reactions involve a [4 + 2] cycloaddition pathway, in which the enamine of the enone acts as the diene and the ketone carbonyl group of the aryl trifluoromethyl ketone acts as the dienophile. In this study, tetrahydropyran derivatives with the desired stereochemistry that are difficult to synthesize by previously reported methods were concisely obtained, and the range of tetrahydropyran derivatives that can be synthesized was expanded. This journal is

Chiral imidazolium prolinate salts as efficient synzymatic organocatalysts for the asymmetric aldol reaction

Chiral imidazolium L-prolinate salts, providing a complex network of supramolecular interaction in a chiral environment, have been studied as synzymatic catalytic systems. They are demonstrated to be green and efficient chiral organocatalysts for direct asymmetric aldol reactions at room temperature. The corresponding aldol products were obtained with moderate to good enantioselectivities. The influence of the presence of chirality in both the imidazolium cation and the prolinate anion on the transfer of chirality from the organocatalyst to the aldol product has been studied. Moreover, interesting match/mismatch situations have been observed regarding configuration of chirality of the two components through the analysis of results for organocatalysts derived from both enantiomers of prolinate (R/S) and the trans/cis isomers for the chiral fragment of the cation. This is associated with differences in the corresponding reaction rates but also to the different tendencies for the formation of aggregates, as evidenced by nonlinear effects studies (NLE). Excellent activities, selectivities, and enantioselectivities could be achieved by an appropriate selection of the structural elements at the cation and anion.

Biomass waste-derived recyclable heterogeneous catalyst for aqueous aldol reaction and depolymerization of PET waste

In this work, we discuss the valorization of biomass waste-derived orange peel ash (OPA) by exploring its applicability as a heterogeneous catalyst in aqueous aldol reactions and demonstrating its versatility by promoting the methanolysis of poly(ethylene terephthalate) (PET) waste. The catalyst was characterized using Fourier-transform infrared spectroscopy (FT-IR), Brunauer-Emmett-Teller (BET) analysis, X-ray powder diffraction (XRD), X-ray fluorescence (XRF), energy dispersive X-ray (EDX) spectroscopy, scanning electron microscopy (SEM), transmission electron microscopy (TEM), X-ray photoelectron spectroscopy (XPS), and thermal gravimetric analysis (TGA) to decode its chemical composition. The aldol reactions were carried out at ambient temperature in the presence of water as a solvent. PET depolymerization was performed in an autoclave for 1 h using only 6% w/w OPA. The catalyst was recovered and reused in both the reactions for up to four successive cycles with minimal loss in the catalytic activity. The use of OPA as a cost-free, eco-friendly and effective recyclable catalyst enables a greener route for C-C bond formation and PET waste recycling.

Enhancing the selectivity of prolinamide organocatalysts using the mechanical bond in [2]rotaxanes

The synthesis of a pair of switchable interlocked prolinamides and their use as organocatalysts in three different enamine-activated processes are reported. A diacylaminopyridine moiety was incorporated into the thread for directing [2]rotaxane formation further allowing the association of complementary small molecules. The rotaxane-based systems were tested as organocatalysts in asymmetric enamine-mediated processes, revealing a significantly improved catalytic ability if compared with the non-interlocked thread. The presence of an electron-withdrawing nitro group at the macrocycle helps to achieve high conversions and enantioselectivities. These systems are able to interact with N-hexylthymine as a cofactor to form supramolecular catalysts displaying a divergent catalytic behaviour. The presence or absence of the cofactor controls the chemoselectivity in competitive reactions.

Access to Spirocyclic Benzothiophenones with Multiple Stereocenters via an Organocatalytic Cascade Reaction

The present report describes an organocatalytic cascade reaction between 2-alkylidene benzo[b]thiophenone derivatives and enones in the presence of the Cinchona alkaloid amine. Spirobenzothiophenonic cyclohexane derivatives containing three stereocenters were prepared via one-step synthesis in yields ranging from 88 to 96% and in enantioselectivities (enantiomeric excess (ee)) ranging from 85 to 97%, with diastereoselectivities of approximately 14/2/1. Therefore, this method provides an efficient route for the synthesis of a new class of optically active 2-spirobenzothiophenones.

A reliable method to create adjacent acid-base pair sites on silica through hydrolysis of pre-anchored amide

A method to create adjacent acid-base pair sites, which are carboxyl and amino groups, respectively, on silica through hydrolysis of pre-anchored amide is proposed. This method can produce an adjacent acid-base pair site. The catalyst showed excellent catalytic performance for aldol condensation of 4-nitrobenzaldehyde with acetone, overwhelming the catalyst having only amino group and an acid-base catalyst prepared in a conventional manner.

RhIII-Catalyzed Synthesis of Highly Substituted 2-Pyridones using Fluorinated Diazomalonate

A RhIII-catalyzed strategy was developed for the rapid construction of highly substituted 2-pyridone scaffolds using α,β-unsaturated oximes and fluorinated diazomalonate. The reaction proceeds through direct, site-selective alkylation based on migratory insertion and subsequent cyclocondensation. A wide substrate scope with different functional groups was explored. The requirement of fluorinated diazomalonate was explored for this transformation. The developed methodology was further extended with the synthesis of the bioactive compound.

Boosting multiple photo-assisted and temperature controlled reactions with a single redox-switchable catalyst: Solvents as internal substrates and reducing agent

An alternative and economically viable process for the synthesis of β-aryl enals, enones and the aryl amines has been developed by partial oxidation of ethanol, isopropanol and N, N-dimethyl formamide (DMF). The formation of β-aryl enals, enones and the aryl amines was catalyzed by a mixed metal oxides layer of cobalt and chromium supported on halloysite nanotubes, designated as CoCr2O4-HNT. The C[sbnd]C and C[sbnd]N bond formation reactions were found to be influenced by temperature and the nature of base. The condensation of aldehyde with in situ generated acetaldehyde by ethanol oxidation forming β-aryl enals occurred selectively at 120 °C. The partial oxidation of isopropanol to acetone and its condensation with aldehydes forming β-aryl enones occurred at room temperature. Increase in temperature caused the liberation of hydrogen gas from isopropanol and allowed the reversible reduction of aldehydes to alcohols. Increase in temperature in isopropanol and increase in base concentration in ethanol causes the selective reduction of aldehydes to alcohols. Besides being active for the Claisen-Schmidt type of reactions and the aryl halides amination process, the synthesized catalyst was also found to be highly active for the photocatalytic oxidation of benzyl alcohols in absence of any external oxidizing agent. The positive holes (h+) generated at the Co(II) site as evident from EPR analysis was considered to be responsible for high photocatalytic activity of the material reducing the recombination rate of holes and electrons (e?). Density Functional Theory calculations were performed to understand the mechanism of ethanol oxidation to acetaldehyde.

Enantioselective Reduction of α,β-Unsaturated Ketones and Aryl Ketones by Perakine Reductase

This report describes the enantioselective reduction of structurally diverse α,β-unsaturated ketones and aryl ketones by perakine reductase (PR) from Rauvolfia. This enzymatic reduction produces α-chiral allylic and aryl alcohols with excellent enantioselectivity and most of the products in satisfactory yields. Furthermore, the work demonstrates 1 mmol scale reactions for product delivery without any detrimental effect on yield and enantioselectivity. The catalytic mechanism, determined by 3D-structure-based modeling of PR and ligand complexes, is also described.

Comparison of deep eutectic solvents and solvent-free reaction conditions for aldol production

In this work, we investigated the catalytic aldolase activity of the porcine pancreas lipase (PPL) for 4-nitrobenzaldehyde (4-NBA) and acetone in different deep eutectic solvent (DES) compared with bovine serum albumin (BSA)-catalyzed aldol reaction. The PPL catalyzed the aldol addition specifically towards the desired aldol product, especially in hydrophobic DES. In contrast to this result, BSA-catalyzed aldol additions did not exhibit specificity for neither aldol nor olefin formation. For the PPL-catalyzed reactions, the product composition could be directly correlated with the choice of DES, differing in their hydrophobicity. The initial reaction velocity of the aldol addition was higher in the hydrophilic DES ChCl:Gly. However, this DES was limited by the solubility for the 4-NBA substrate. The 4-NBA containing DES exhibited the highest solubility for 4-NBA. However, the fastest reaction with a final yield of 1296.5 mM, which corresponds to 71% yield and 82% conversion after 32 h, was achieved in the co-solvent acetone, making this reaction solvent-less and improving the productivity up to 40.5 mM h?1 compared to reactions performed in DES.