52287-53-3

Usage

Type of compound

Nitroalkene derivative

Functional groups

Nitro group and phenyl group

Common use

Organic synthesis

Potential applications

Production of pharmaceuticals and agrochemicals

Reactivity

Reactive nature

Use as a reagent

Introduces nitrophenyl and nitropropene functional groups into organic molecules

Research interest

Biological activity and medicinal chemistry

InChI:InChI=1/C9H8N2O4/c1-7(10(12)13)6-8-2-4-9(5-3-8)11(14)15/h2-6H,1H3/b7-6+

Upstream product

• 79-24-3 Nitroethane 
• 555-16-8 4-nitrobenzaldehdye 
• 619-73-8 4-nitrobenzyl chloride 
• 142839-98-3 2-nitro-1-(4-nitrophenyl)propan-1-ol 

Downstream Products

• 5332-96-7 1-(4-nitrophenyl)propan-2-one 
• 29865-60-9 1-nitro-4-(2-nitropropyl)benzene 
• 94814-67-2 4-(2-Nitro-propyl)-phenylamine 
• 222026-08-6 4-methyl-3-(4-nitro-phenyl)-1H-pyrrole-2-carboxylic acid tert-butyl ester 
• 222026-53-1 1,4-dimethyl-3-(4-nitro-phenyl)-1H-pyrrole-2-carboxylic acid tert-butyl ester 
• 222026-55-3 1-allyl-4-methyl-3-(4-nitro-phenyl)-1H-pyrrole-2-carboxylic acid tert-butyl ester 
• 222026-56-4 1-benzyl-4-methyl-3-(4-nitro-phenyl)-1H-pyrrole-2-carboxylic acid tert-butyl ester 
• 95838-64-5 2,5-Dimethyl-4-(4-nitrophenyl)-3-pyrrolcarbonsaeure-ethylester 

Relevant academic research and scientific papers

Design and synthesis of a novel quinoxaline diamine and its polyimides with high-Tg and red color

To produce high-temperature polyimide (PI) films meeting the demand of flexible-display, heteroaromatic monomers were extensively investigated. Quinoxaline is one kind of the most important N-heterocycles, which possesses pharmacological activities and thermotolerance. In this work, newly designed diamine monomer 3/2-(4-aminophenyl)-2/3-methylquinoxalin-6-amine (QMDA) was successfully synthesized. Their corresponding quinoxaline-containing PI films were prepared by cooperating QMDA with several aromatic dianhydrides, and divided into two series according to different thermal imidization procedures. The firm scaffold of quinoxaline was proved to enhance the thermal stability of the obtained PIs. The effect of final annealing temperature on molecular packing and thermal properties of the PI films was also investigated. Under higher annealing temperature, PI films were found to pack more tightly due to the formation of more cross-linkings in polymer matrix. The restriction of chian movements brought these PIs higher Tg more than 500 °C or even prevented the occurace of glass transition.

Nitroalkyl quinoxaline or derivatives thereof, aminoalkyl quinoxaline or derivatives thereof and synthesis method thereof

The invention relates to a method for synthesizing nitroalkyl quinoxaline or derivatives thereof. The method includes the following step of making mono-nitro-substituted o-phenylenediamine or derivatives thereof and nitroalkenyl-substituted benzene or derivatives thereof react in a solvent for a preset time duration in the presence of a catalyst to obtain the nitroalkyl quinoxaline or derivativesthereof. The invention further relates to the nitroalkyl quinoxaline or derivatives thereof, and further relates to aminoalkyl quinoxaline or derivatives thereof and a preparing method thereof. Raw materials applied in the methods are low in price and easy to obtain, the synthesis process is simple, and the obtained target aminoalkyl quinoxaline or derivatives thereof are easy to separate.

Regioselective Opening of Nitroepoxides with Unsymmetrical Diamines

Nitroepoxides are easily transformed into benzodiazepines, tetrahydrobenzodiazepines, imidazopyridines, and N-alkyl tetrahydroquinoxalines by treatment with 2-aminobenzylamines, 2-aminopyridines, and N-alkyl 1,2-diaminobenzenes, respectively. Regioselectivity is controlled through attack of the most nucleophilic nitrogen of the unsymmetrical diamine to the β position of the epoxide. These reactions represent an efficient way to prepare privileged bioactive structures.

Catalyst- and Substituent-Controlled Switching of Chemoselectivity for the Enantioselective Synthesis of Fully Substituted Cyclobutane Derivatives via 2 + 2 Annulation of Vinylogous Ketone Enolates and Nitroalkene

The first regioselective, diastereoselective, and enantioselective organocatalyzed Michael-Michael cascade of vinylogous ketone enolates and nitroalkenes for the construction of fully substituted cyclobutanes is achieved by the deployment of the appropriate chiral squaramide catalyst and the pertinent substituent on the substrate. The domino reaction provided cyclobutanes with four contiguous stereocenters, including a quaternary center in good yields with diastereomeric ratio of >20:1 and with enantioselectivities of mostly up to 98% enantiomeric excess (ee). The structures and the absolute configurations of the adducts were confirmed by single-crystal X-ray crystallographic analyses of the appropriate products.

Enantioselective hydrogenation of α,β-disubstituted nitroalkenes

The first highly chemo- and enantioselective hydrogenation of α,β-disubstituted nitroalkenes was accomplished with rhodium/JosiPhos-J2 as a catalyst, with the yield and enantioselectivity of up to 95% and 94%, respectively. The α-chiral nitroalkanes will provide an entry to valuable chiral amphetamines which are otherwise not so easily accessed. This journal is the Partner Organisations 2014.

Synthesis of nitroalkenes involving a cooperative catalytic action of iron(III) and piperidine: A one-pot synthetic strategy to 3-alkylindoles, 2H-chromenes and N-arylpyrrole

An efficient and simple strategy has been developed to synthesize various substituted nitroalkenes involving a cooperative catalytic system of FeCl 3 and piperidine. This dual catalytic protocol simultaneously activates both electrophile and nucleophile and works under mild reaction conditions so that many sensitive functional groups were tolerated. Moreover, this cooperative catalytic reaction is also suitable for various one-pot reactions involving nitroalkenes such as, 2H-chromenes, N-arylpyrrole and Michael reaction with indole. Notably, this method is low-cost, efficient and environmentally friendly. Copyright

Adapting to substrate challenges: Peptides as catalysts for conjugate addition reactions of aldehydes to α,β-disubstituted nitroolefins

Conjugate addition reactions of aldehydes to α,β-disubstituted nitroolefins are important because they provide synthetically useful γ-nitroaldehydes bearing three consecutive stereogenic centers. Such reactions are challenging due to the drastically lower reactivity of α,β-disubstituted nitroolefins compared to, for example, β-monosubstituted nitroolefins. The testing of a small collection of peptides of the type Pro-Pro-Xaa (Xaa=acidic amino acid) led to the identification of H-Pro-Pro-D-Gln-OH and H-Pro-Pro-Asn-OH as excellent stereoselective catalysts for this transformation. In the presence of 5a mol% of these peptides different combinations of aldehydes and α,β- disubstituted nitroolefins react readily with each other providing γ-nitroaldehydes in good yields and diastereoselectivities as well as excellent enantioselectivities. Chiral pyrrolidines as well as fully substituted γ-butyrolactams and γ-amino acids are easily accessible from the γ-nitroaldehydes. Mechanistic studies demonstrate that the configuration at all three stereogenic centers is induced by the peptidic catalysts. Only a minimal amount of products from homo-aldol reactions is observed demonstrating the high chemoselectivity of the peptidic catalysts. α,β- Disubstituted nitroolefins are challenging electrophiles due to their low reactivity. The modular nature of peptides of the type Pro-Pro-Xaa (Xaa=acidic amino acid; see scheme) allowed for the identification of H-Pro-Pro-D-Gln-OH and H-Pro-Pro-Asn-OH as very good catalysts for the conjugate addition reaction of aldehydes to α,β-disubstituted nitroolefins. Mechanistic studies demonstrate that the peptides induce the configuration at each of the stereogenic centers. Copyright

Design, synthesis, and biological evaluation of 4-phenylpyrrole derivatives as novel androgen receptor antagonists

A series of 4-phenylpyrrole derivatives D were designed, synthesized, and evaluated for their potential as novel orally available androgen receptor antagonists therapeutically effective against castration-resistant prostate cancers. 4-Phenylpyrrole compou

Selective nitroaldol condensations over heterogeneous catalysts in the presence of supercritical carbon dioxide

(Chemical Equation Presented) At 40-60°C, in the presence of heterogeneous catalysts based on Al2O3, supercritical carbon dioxide not only acts as a good solvent for the reaction of aromatic and aliphatic aldehydes with 1-nitroalkanes but, most importantly, it also allows the selectivity to be tuned between the competitive formation of β-nitroalcohols and nitroalkenes (from the Henry reaction and the nitroaldol condensation, respectively). In particular, when the pressure (and the density) of the supercritical phase is enhanced from 80 to 140 bar, the nitroalkene's selectivity increases, on average, from ～60 to >90%. Experiments show that, in the same pressure range, a steep increase of the concentration profiles of reactant aldehydes takes place. By contrast, under solvent-free conditions, the reaction usually proceeds with a higher conversion, but nitroalkanols are the major products.

Solvent-free nucleophilic addition of N-alkylhydroxylamines to substituted nitroolefins: Formation of nitrones by a tandem process

Nucleophilic addition of 1-methyl-2-arylethylhydroxylamine to substituted β-nitrostyrene under solvent-free conditions has led to unexpected nitrones via a tandem process involving 1,4-addition and elimination. Copyright Taylor & Francis Group, LLC.