58497-32-8

Upstream product

• 6125-24-2 2-Phenylnitroethane 
• 100-52-7 benzaldehyde 
• 102-96-5 (2-nitroethenyl)benzene 
• 62634-73-5 Acetic acid 1-benzyl-2-nitro-2-phenyl-ethyl ester 
• 62753-15-5 3-nitro-1,3-diphenyl-1-propene 
• 71-43-2 benzene 

Downstream Products

• 1321574-08-6 3-benzyl-1-methyl-3-nitro-4-phenylpyrrolidine 
• 1321574-11-1 3'-benzyl-1'-methyl-3'-nitro-4'-phenylspiro[indoline-3,2'-pyrrolidin]-2-one 
• 1078126-49-4 C₁₅H₁₃N₃ 
• 69957-35-3 2-nitro-1,3-diphenylpropane 
• 114090-88-9 trans-5,5-dibenzyl-1-hydroxy-4-methyl-3-phenylthiopyrrolidin-2-one 
• 114090-88-9 cis-5,5-dibenzyl-1-hydroxy-4-methyl-3-phenylthiopyrrolidin-2-one 
• 114090-52-7 (E)-4-benzyl-4-nitro-5-phenylpent-2-enal ethylene acetal 
• 89188-71-6 (Z)-4-benzyl-4-nitro-5-phenylpent-2-enal ethylene acetal 
• 114090-86-7 trans-5,5-dibenzyl-1-hydroxy-3-hydroxymethyl-4-methylpyrrolidin-2-one 
• 114090-86-7 cis-5,5-dibenzyl-1-hydroxy-3-hydroxymethyl-4-methylpyrrolidin-2-one 
• 89188-68-1 methyl (E)-4-benzyl-4-nitro-5-phenylpent-2-enoate 
• 89188-67-0 methyl (Z)-4-benzyl-4-nitro-5-phenylpent-2-enoate 
• 114090-50-5 (E)-4-benzyl-4-nitro-5-phenylpent-2-en-1-ol 
• 89188-69-2 (Z)-4-benzyl-4-nitro-5-phenylpent-2-en-1-ol 

Relevant academic research and scientific papers

Acylation of Nitronates: [3,3]-Sigmatropic Rearrangement of in Situ Generated N-Acyloxy, N-oxyenamines

Acylation of nitronates affords α-acyloxyoxime derivatives via an umpolung functionalization of the α-position. This transformation involves generation of hitherto unknown N-acyloxy,N-oxyenamines and their fast [3,3]-sigmatropic rearrangement driven by the cleavage of the weak N-O bond. The reaction has a broad scope, and it is regioselective in the case of nitronates possessing nonsymmetrically substituted α-positions. Application to the formal total synthesis of clausenamide and cis-clausenamide is presented.

Synthesis, antiproliferative and pro-apoptotic effects of nitrostyrenes and related compounds in Burkitt’s lymphoma

Background: Cancers of the lymphatic cells (lymphomas) account for approximately 12% of malignant diseases worldwide. The nitrostyrene scaffold is identified as a lead target structure for the development of particularly effective compounds targeting Burkitt’s lymphoma (BL). Objectives: The aims of the curent study were to synthesise a panel of nitrostyrene compounds and to evaluate their activity in Burkitt’s lymphoma (BL). Methods: A panel of structurally varied compounds were designed and synthesised using Henry Knoevenagel condensation reactions. Single crystal X-Ray analysis confirmed the E configuration for six examples of these novel structures. A number of nitrostyrene-related compounds were also investigated including 1,3-bis(aryl)-2-nitropropenes together with heterocyclic scaffolds containing the nitrovinyl pharmacophore such as 3-nitro-2-phenyl-2H-chromenes. The antiproliferative activities of the compounds were evaluated using the BL cell lines EBV- MUTU-1 and EBV+ DG-75 (chemoresistant) to establish preliminary structure-activity relationships. Results: Lead compounds with optimized nitrostyrene scaffolds and 3-nitro-2-phenyl-2Hchromene structures were successfully established with typical IC50 values of 0.45 μM and 0.47 μM in MUTU-1 cells and 1.41 μM and 1.92 μM, respectively, in DG-75 cells. The mechanism of cell death was identified as apoptotic and the lead compound was found to elicit comparable apoptotic effects to Taxol in Burkitt’s lymphoma cell lines MUTU-1 and DG-75. Conclusion: This class of pharmaceutically active compounds with potential for the treatment of Burkitt’s lymphoma suggest a potential role for nitrostyrene based agents in chemotherapy.

First Friedel-Crafts reaction of the Baylis-Hillman adducts derived from nitroolefins: Application towards synthesis of pyrrolidines and spiropyrrolidines

A general and simple protocol for the arylation of Baylis-Hillman adducts derived from nitroolefins leading to novel classes of (E)-2-nitro-1,3- diarylprop-1-enes and 1-[(E)-2-nitro-3-arylallyl]naphthalenes via an intermolecular Friedel-Crafts reaction ha

A modified Horner-Wadsworth-Emmons reaction for the synthesis of nitroalkenes

A range of trisubstituted nitroalkenes are available from the reaction of an α-nitrophosphonate anion and an aldehyde in tetrahydrofuran under reflux.

Biosynthesis of Porphyrins and Related Macrocycles. Part 29. Synthesis and Chemistry of 2,2-Disubstituted 2H-Pyrroles (Pyrrolenines)

Syntheses are described of three 2H-pyrroles (pyrrolenines), (15), (28), and (64), which were designed to test the chemical feasibility of the rearrangements proposed as part of the mechanism of the enzyme cosynthetase (uroporphynogen III synthase).All three syntheses create the 2H-pyrrole ring by the Michael addition of nitronate anion to an α,β-unsaturated ester and one introduces an additional substituent by novel alkylations of the dianion of a hydroxamic acid.Some of intermediates in the syntheses showed unusual n.m.r. properties which reveal strong conformational preferences.The rearrangement of the 2H-pyrroles was studied under both thermal and acid-catalysed conditions.The results show that 2,2-disubstituted 2H-pyrroles only rearrange easily by -sigmatropic shifts if they do not have further substituents on C-3 and C-4. 2-Pyrrolylmethyl-2H-pyrroles prefer to rearrange by a fragmentation-recombination mechanism.