22399-00-4

Usage

Uses

Used in Agricultural Industry:
Propanedioic acid, 2-[(4-nitrophenyl)Methylene]-, 1,3-diethyl ester is used as a potential intermediate in the preparation of fungicides derived from the modification of Diethyl-2-benzylidenemalonate. Its application in this industry is aimed at providing effective solutions for controlling fungal infections in crops, thereby enhancing agricultural productivity and crop protection.

Upstream product

• 555-16-8 4-nitrobenzaldehdye 
• 105-53-3 diethyl malonate 
• 15482-93-6 p-Nitro-benzyl-chlormalonsaeure-diaethylester 
• 631-22-1 diethyl dibromomalonate 
• 685-87-0 Diethyl 2-bromomalonate 
• 5292-53-5 diethyl benzalmalonate 
• 584-45-2 2-benzylidenemalonic acid 
• 14064-10-9 diethyl 2-chloromalonate 
• 7598-70-1 diethyl 2-(4-nitrobenzyl)malonate 
• 123-30-8 4-amino-phenol 
• 100-11-8 1-bromomethyl-4-nitro-benzene 

Downstream Products

• 54267-71-9 3-(4-nitrophenyl)-2-carboxy-2-propenoic acid 
• 78136-58-0 diethyl (4-aminobenzyl)malonate 
• 62558-74-1 2-acetyl-4-ethoxycarbonyl-3-(4-nitrophenyl)pentanedioic acid diethyl ester 
• 1098240-66-4 (2-cyano-1,5-diethoxy-4-(ethoxycarbonyl)-3-(4-nitrophenyl)-1,5-dioxopentan-2-yl)potassium 
• 1098240-69-7 C₁₇H₁₆N₃O₆^(1-)*K⁽¹⁺⁾ 

Relevant academic research and scientific papers

Integration of heterogeneous catalysts into complex synthetic routes: Sequential vs. one-pot reactions in a (Knoevenagel + Mukaiyama-Michael + hydrogenation + transesterification) sequence

Heterogeneous catalysts of different nature can be combined in one-pot tandem reactions, but the compatibility issues of catalysts with reagents, products, and by-products make more convenient the application of a sequential procedure, in which the catalyst is filtered after each reaction and the crude is used in the following reaction without purification. In this way the recovery and reuse of each catalyst can be optimized to obtain the maximum productivity. The nature of the reactions, and the catalysts involved in them, conditions the maximum number of successive steps in the sequence. In the case of the (Knoevenagel + Mukaiyama-Michael + hydrogenation + transesterification) process tested in this work, the optimal results are obtained when the sequential method is applied to only three reactions, whereas the four reactions sequence shows limitations in the yield of the last transesterification step. The Royal Society of Chemistry 2013.

Synthesis, molecular docking, α-glucosidase inhibition, and antioxidant activity studies of novel benzimidazole derivatives

A novel series of N-methyl/benzyl-substituted benzimidazolyl-linked para-substituted benzyl-based compounds containing 2,4-thiazolidinediones, dimethyl malonate (DMM), and diethyl malonate (DEM) 17–27 were designed, docked, synthesized, and evaluated for their antidiabetic activity studies. Structures of all the synthesized compounds were confirmed through 1H NMR, 13C NMR, FTIR, and mass spectrometry. Four targeted compounds (17–18 and 22–23) showed good inhibitory potential in the range of 4.10 ± 0.01 to 9.12 ± 0.06 μM. Furthermore, synthesized compounds 17–27 were evaluated for their antioxidant potential and compared with standard ascorbic acid and results showed that compound 18 (EC50 = 0.176 ± 0.002 mM) being the most active. Compounds 17–18 and 22–23 exhibited prominent antidiabetic as well as antioxidant activity. Compound 18 was considered a promising candidate for this series. The designed molecules were docked into α-glucosidase protein (PDB Code. 3TOP) to develop a correlation with the α-glucosidase inhibition studies and were also additionally docked into PPARγ proteins (PDB ID: 2PRG) with rosiglitazone (standard drug) to study their PPARγ binding affinity in comparison with rosiglitazone and to classify these compounds for their PPARγ agonistic behavior.

Programmed Sequential Additions to Halogenated Mucononitriles

Dihalomucononitriles were synthesized and their reactivity evaluated to assess their ability to function as linchpin reagents. Bis(2-chloroacrylonitrile) and bis(2-bromoacrylonitrile) were synthesized from 2,1,3-benzothiadiazole and undergo conjugate addition/elimination reactions with both nitrogen (40-95% yield) and carbon nucleophiles (72-93% yield). Secondary amines undergo monosubstitutions, while carbon nucleophiles are added twice. The sequence of addition of the nucleophiles could be controlled to give mixed addition products. The multicomponent coupling products could then be converted to natural product like motifs using intramolecular cyclization reactions.

[3+2] cycloadditions: Part XXXIV: Further investigations of cycloadditions of C,N-diaryl- and C-aryl-N-methyl nitrones to α,β-unsaturated esters

Investigations of [3+2] cycloadditions of C,N-diaryl and C-aryl-N-methyl nitrones as three atom components (TAC) to substituted methyl E-cinnamates and diethyl arylidene malonates have been further investigated. [3+2] Cycloadditions of cinnamates yielded mixtures of cycloadducts, the major products being the 3,4-trans-4,5-trans-2,3,5-triaryl-4-carbomethoxy products originating from the endo-carbonyl-exo-aryl meta channel approach of the cinnamate component. [3+2] Cycloadditions to diethyl arylidene malonates furnished single cycloadducts-3,5-trans-2-methyl-3,5-diaryl-4,4-dicarbethoxy isoxazolidines by a endo-aryl meta channel approach of the 2π-component.

Stereoselective synthesis of vic-halohydrins and an unusual Knoevenagel product from an organocatalyzed aldol reaction: A non-enamine mode

Stereoselective synthesis by an aldol reaction between chloroacetone and aldehyde was studied using a synthesized chiral organocatalyst and triethylamine. The reaction gave α-chloro-β-hydroxy ketones in excellent yield with high anti selectivity and enantioselectivity. The chiral organocatalyst was also used in the Knoevenagel reaction, which gave α-cyano-β-hydroxy ketones at a low temperature and the usual Knoevenagel product at a high temperature. Both products were obtained in good to moderate yield with good anti selectivity in the case of α-cyano-β-hydroxy ketone derivatives.

Design and synthesis of 6-oxo-1,4,5,6-tetrahydropyrimidine-5-carboxylate derivatives as neuraminidase inhibitors

A series of 6-oxo-1,4,5,6-tetrahydropyrimidine-5-carboxylate derivatives were prepared to evaluate their ability of inhibiting neuraminidase (NA) of influenza A virus. All the compounds were synthesized in good yields starting from aldehyde by using a suitable synthetic strategy, which showed moderate inhibitory activity against influenza A NA. Compound 6g exhibited the strongest inhibitory activity against influenza virus A NA (IC50 = 17.64 μM), which indicated pyrimidine ring could be used as a core structure to design novel influenza NA inhibitors.

Asymmetric michael addition of N-tert-butanesulfinyl imidate with α,β-unsaturated diesters: Scope and application to the synthesis of indanone derivatives

An additive-free and highly diastereoselective Michael addition reaction of an N-tert-butanesulfinyl imidate to α,β-unsaturated diesters has been developed using LDA as a base with good to excellent yields. The utility of this chemistry is further demonstrated by the asymmetric synthesis of 3-substituted indanone derivatives 8a, 8d, 8e, and 8i with high enantiomeric excess, which are potential building blocks for preparing biologically active lead compounds.

Nickel(ii)-catalyzed enantioselective 1,3-dipolar cycloaddition of azomethine imines with alkylidene malonates

We demonstrated an asymmetric 1,3-dipolar cycloaddition of azomethine betaines with alkylidene malonates by using a chiral N,N'-dioxide- NiII complex as a catalyst. Both aromatic- and aliphatic-substituted alkylidene malonates were found to be suitable for the reaction. A range of transpyrazolone derivatives was exclusively obtained with excellent yields (up to 99% yield) and good enantioselectivities (up to 97% ee) under mild reaction conditions. The reaction could be carried out on a gram scale with the good results being maintained. Control experiments were performed to elucidate the specific diastereoselectivity of the reaction. The formation of single trans isomers was dominated by secondary orbital interactions between the ester groups of the dipolarophile and the azomethine imine. On the basis of the experimental results and previous reports, a possible catalytic model was assumed.

Determination of thermodynamic affinities of various polar olefins as hydride, hydrogen atom, and electron acceptors in acetonitrile

A series of 69 polar olefins with various typical structures (X) were synthesized and the thermodynamic affinities (defined in terms of the molar enthalpy changes or the standard redox potentials in this work) of the polar olefins obtaining hydride anions, hydrogen atoms, and electrons, the thermodynamic affinities of the radical anions of the polar olefins (X ?-) obtaining protons and hydrogen atoms, and the thermodynamic affinities of the hydrogen adducts of the polar olefins (XH?) obtaining electrons in acetonitrile were determined using titration calorimetry and electrochemical methods. The pure Ci - 'C π-bond heterolytic and homolytic dissociation energies of the polar olefins (X) in acetonitrile and the pure Ci - 'C π-bond homolytic dissociation energies of the radical anions of the polar olefins (X?-) in acetonitrile were estimated. The remote substituent effects on the six thermodynamic affinities of the polar olefins and their related reaction intermediates were examined using the Hammett linear free-energy relationships; the results show that the Hammett linear free-energy relationships all hold in the six chemical and electrochemical processes. The information disclosed in this work could not only supply a gap of the chemical thermodynamics of olefins as one class of very important organic unsaturated compounds but also strongly promote the fast development of the chemistry and applications of olefins.

Asymmetric michael addition of ketones to alkylidene malonates and allylidene malonates via enamine - Metal lewis acid bifunctional catalysis

Novel enamine-metal Lewis acid bifunctional catalysts were successfully applied to the asymmetric Michael addition of ketones to alkylidene malonates, offering excellent stereoselectivity (up to >99% ee and >99:1 dr). The asymmetric Michael addition of ketones to allylidene malonates was also achieved.