Category: 5153-73-1

Kumar, Saurabh published the artcileAIBN-Initiated Denitrative Cross-Coupling Reactions of β-Nitrostyrenes with Sulfonyl Hydrazides/Disulfides: A Metal-free Approach towards Vinyl Sulfones, Computed Properties of 5153-73-1, the publication is Asian Journal of Organic Chemistry (2018), 7(2), 359-362, database is CAplus.

A practical and metal free approach involving denitrative coupling of β-nitrostyrenes and sulfonyl hydrazides/disulfides by AIBN (azobisisobutyronitrile) was developed to accomplish the synthesis of vinyl sulfones I [R = Ph, 4-ClC₆H₄, 2-thienyl, etc.; R¹ = 4-MeC₆H₄, Bn, 2-naphthyl, etc.]. The method employed easily accessible starting materials and was endowed with a broad substrate scope, functional group tolerance and high yields.

Asian Journal of Organic Chemistry published new progress about 5153-73-1. 5153-73-1 belongs to nitriles-buliding-blocks, auxiliary class Nitrile,Alkenyl,Nitro Compound,Benzene, name is (E)-4-(2-Nitrovinyl)benzonitrile, and the molecular formula is C9H6N2O2, Computed Properties of 5153-73-1.

Referemce:
https://en.wikipedia.org/wiki/Nitrile,
Nitriles – Chemistry LibreTexts

Yin, Shu-Qiang published the artcilePreparation of S14161 and its analogues and the discovery of 6-bromo-8-ethoxy-3-nitro-2H-chromene as a more potent antitumor agent in vitro, Recommanded Product: (E)-4-(2-Nitrovinyl)benzonitrile, the publication is Bioorganic & Medicinal Chemistry Letters (2013), 23(11), 3314-3319, database is CAplus and MEDLINE.

The small chem. compound 8-ethoxy-2-(4-fluorophenyl)-3-nitro-2H-chromene (S14161) was recently identified as an inhibitor of the phosphoinositide 3-kinase (PI3K). In the present study, the authors designed a novel synthesis of S14161 and prepared a series of its analogs via the oxa-Michael-Henry reaction in the presence of catalytic amounts of l-proline and triethylamine. Further structural simplification led to the identification of 6-bromo-8-ethoxy-3-nitro-2H-chromene (I, BENC-511) that exhibited potent antiproliferative activities against a panel of 12 tumor cell lines. Compared with S14161, BENC-511 was more potent in blocking the AKT phosphorylation and inducing cancer cell apoptosis. BENC-511 also displayed more potent effects on human umbilical vein epithelial cells (HUVEC) migration, suggesting its anti-angiogenesis activity.

Bioorganic & Medicinal Chemistry Letters published new progress about 5153-73-1. 5153-73-1 belongs to nitriles-buliding-blocks, auxiliary class Nitrile,Alkenyl,Nitro Compound,Benzene, name is (E)-4-(2-Nitrovinyl)benzonitrile, and the molecular formula is C10H10O2, Recommanded Product: (E)-4-(2-Nitrovinyl)benzonitrile.

Referemce:
https://en.wikipedia.org/wiki/Nitrile,
Nitriles – Chemistry LibreTexts

Hamzehloueian, Mahshid published the artcileAn experimental and theoretical study on the regioselective synthesis of a new class of spiropyrrolothiazoles with quinoxaline motifs via a 1,3-dipolar cycloaddition reaction. An evaluation of DFT methods, Quality Control of 5153-73-1, the publication is RSC Advances (2015), 5(93), 76368-76376, database is CAplus.

A series of novel spiropyrrolothiazoles I (R = Ph, 4-MeC₆H₄, 2-O₂NC₆H₄, 2-furyl, 2-thienyl, 1-naphthyl, etc.) with quinoxaline motifs was synthesized by a four-component 1,3-dipolar cycloaddition reaction of various trans-β-nitroalkenes RCH:CHNO₂ and an azomethine ylide, generated in situ from 1,3-thiazolidine-4-carboxylic acid, ninhydrin and 1,2-phenylenediamine. The stereochem. of the products was confirmed by single crystal X-ray structure and spectroscopic techniques. Theor. calculations were carried out using DFT methods at the B3LYP/6-31G(d,p), wB97xD/6-31G(d,p) and M06-2X/6-31G(d,p) levels. The regio- and stereoselectivity was explained on the basis of transition state stabilities and global and local reactivity indexes of the reactants. The assessment of geometries and energetics of transition states revealed the importance of π/π interactions between aromatic rings in the regioselectivity of the cycloaddition reaction. The B3LYP functional was unable to deal with this weak interaction in the proposed TSs and led to an incorrect conclusion about the reaction regioselectivity. In this report, wB97xD and M06-2X functionals to calculate the transition states relative energies were successfully employed.

RSC Advances published new progress about 5153-73-1. 5153-73-1 belongs to nitriles-buliding-blocks, auxiliary class Nitrile,Alkenyl,Nitro Compound,Benzene, name is (E)-4-(2-Nitrovinyl)benzonitrile, and the molecular formula is C9H6N2O2, Quality Control of 5153-73-1.

Referemce:
https://en.wikipedia.org/wiki/Nitrile,
Nitriles – Chemistry LibreTexts

Jalal, Swapnadeep published the artcileSynthesis 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, Category: nitriles-buliding-blocks, the publication is European Journal of Organic Chemistry (2013), 2013(22), 4823-4828, database is CAplus.

An efficient and simple strategy has been developed to synthesize various substituted nitroalkenes involving a cooperative catalytic system of FeCl₃ 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.

European Journal of Organic Chemistry published new progress about 5153-73-1. 5153-73-1 belongs to nitriles-buliding-blocks, auxiliary class Nitrile,Alkenyl,Nitro Compound,Benzene, name is (E)-4-(2-Nitrovinyl)benzonitrile, and the molecular formula is C9H6N2O2, Category: nitriles-buliding-blocks.

Referemce:
https://en.wikipedia.org/wiki/Nitrile,
Nitriles – Chemistry LibreTexts

Alimohammadi, Kamal published the artcileAn expedient approach for the regio- and stereoselective synthesis of novel spiroindolizidines via [3+2] cycloaddition, Category: nitriles-buliding-blocks, the publication is Comptes Rendus Chimie (2014), 17(2), 156-163, database is CAplus.

A new series of spiroindolizidines was synthesized by one-pot, three-component condensation of azomethine ylides, generated from 1,2,3,4-tetrahydroisoquinoline with ninhydrin or isatin derivatives by a 1,5-prototropic shift route, with various derivatives of trans-β-nitrostyrene in a regio- and stereoselective manner. X-ray crystal structure anal. and NMR confirmed the structure outcome of the cycloaddition reaction.

Comptes Rendus Chimie published new progress about 5153-73-1. 5153-73-1 belongs to nitriles-buliding-blocks, auxiliary class Nitrile,Alkenyl,Nitro Compound,Benzene, name is (E)-4-(2-Nitrovinyl)benzonitrile, and the molecular formula is C9H6N2O2, Category: nitriles-buliding-blocks.

Referemce:
https://en.wikipedia.org/wiki/Nitrile,
Nitriles – Chemistry LibreTexts

Huang, Shengying published the artcileAsymmetric sequential double Michael reactions of γ,δ-unsaturated β-ketoesters to nitroolefins catalyzed by Ni (II)-diamine complex, HPLC of Formula: 5153-73-1, the publication is Catalysis Communications (2017), 67-70, database is CAplus.

The asym. sequential double Michael reactions of γ,δ-unsaturated β-ketoesters and nitroolefins catalyzed by 2 mol% of readily prepared Ni(II)-bis[(R,R)-N,N’-dibenzylcyclohexane-1,2-diamine] complex and then with 1 equiv of tetramethylguanidine (TMG) for cyclization have been developed. The reaction gave the corresponding Michael adducts of multifunctional cyclohexenol derivatives with three chiral stereocenters in good yields, moderate diastereoselectivities, and high enantioselectivities under mild reaction conditions. Thus, e.g., γ,δ-unsaturated β-ketoester I + trans-β-nitrostyrene â†?II (82%, dr = 5:1, 92% ee).

Catalysis Communications published new progress about 5153-73-1. 5153-73-1 belongs to nitriles-buliding-blocks, auxiliary class Nitrile,Alkenyl,Nitro Compound,Benzene, name is (E)-4-(2-Nitrovinyl)benzonitrile, and the molecular formula is C9H6N2O2, HPLC of Formula: 5153-73-1.

Referemce:
https://en.wikipedia.org/wiki/Nitrile,
Nitriles – Chemistry LibreTexts

Guo, Xing-Tao published the artcileHighly enantioselective Michael addition of α,α-disubstituted aldehydes to nitroolefins, SDS of cas: 5153-73-1, the publication is Research on Chemical Intermediates (2016), 42(7), 6373-6380, database is CAplus.

A highly enantioselective Michael addition reaction of α,α-disubstituted aldehydes to β-nitrostyrenes has been developed. In the presence of rosin-based chiral primary amine-thiourea, γ-nitroaldehydes I [ Ar = 4-NO₂C₆H₄, 2-NO₂C₆H₄, 4-CNC₆H₄, 4-CF₃C₆H₄, 4-FC₆H₄, 2-furyl, etc.; R¹ = Me, Et; R² = Et, n-Pr, Ph, etc.; R¹= R² = (CH₂)₅] were afforded in excellent enantioselectivities (up to 99 % ee) with up to 99 % yield.

Research on Chemical Intermediates published new progress about 5153-73-1. 5153-73-1 belongs to nitriles-buliding-blocks, auxiliary class Nitrile,Alkenyl,Nitro Compound,Benzene, name is (E)-4-(2-Nitrovinyl)benzonitrile, and the molecular formula is C9H6N2O2, SDS of cas: 5153-73-1.

Referemce:
https://en.wikipedia.org/wiki/Nitrile,
Nitriles – Chemistry LibreTexts

Wang, Jian-Shu published the artcileAcOH-catalyzed aza-Michael addition/N-nitrosation: An efficient approach to CF₂HCH₂-containing N-nitrosoamines, Name: (E)-4-(2-Nitrovinyl)benzonitrile, the publication is Tetrahedron (2018), 74(28), 3904-3911, database is CAplus.

A simple and highly efficient protocol for the AcOH-catalyzed three-component reaction of nitroalkenes, difluoroethylamine and tert-Bu nitrite through cascade aza-Michael addition/N-nitrosation has been developed. A range of CF₂HCH₂-containing N-nitrosoamines were obtained in good to excellent yields. This approach features easily available cheap materials, without using addnl. organic solvents, simple operation under room temperature, gram scalable preparation and functionally diverse products.

Tetrahedron published new progress about 5153-73-1. 5153-73-1 belongs to nitriles-buliding-blocks, auxiliary class Nitrile,Alkenyl,Nitro Compound,Benzene, name is (E)-4-(2-Nitrovinyl)benzonitrile, and the molecular formula is C8H7N3, Name: (E)-4-(2-Nitrovinyl)benzonitrile.

Referemce:
https://en.wikipedia.org/wiki/Nitrile,
Nitriles – Chemistry LibreTexts

Quan, Xue-Jing published the artcilep-Toluenesulfonic Acid Mediated 1,3-Dipolar Cycloaddition of Nitroolefins with NaN₃ for Synthesis of 4-Aryl-NH-1,2,3-triazoles [Erratum to document cited in CA161:682131], Name: (E)-4-(2-Nitrovinyl)benzonitrile, the publication is Organic Letters (2015), 17(2), 393, database is CAplus and MEDLINE.

On page 5730, structure 4a in Scheme 2 was published incorrectly, and subsequent text corresponding to this Structure is also incorrect; the correct structure, name, and text are given.

Organic Letters published new progress about 5153-73-1. 5153-73-1 belongs to nitriles-buliding-blocks, auxiliary class Nitrile,Alkenyl,Nitro Compound,Benzene, name is (E)-4-(2-Nitrovinyl)benzonitrile, and the molecular formula is C9H6N2O2, Name: (E)-4-(2-Nitrovinyl)benzonitrile.

Referemce:
https://en.wikipedia.org/wiki/Nitrile,
Nitriles – Chemistry LibreTexts

Quan, Xue-Jing published the artcilep-Toluenesulfonic Acid Mediated 1,3-Dipolar Cycloaddition of Nitroolefins with NaN₃ for Synthesis of 4-Aryl-NH-1,2,3-triazoles, Safety of (E)-4-(2-Nitrovinyl)benzonitrile, the publication is Organic Letters (2014), 16(21), 5728-5731, database is CAplus and MEDLINE.

A p-TsOH-mediated 1,3-dipolar cycloaddition of nitroolefins and sodium azide for the synthesis of 4-aryl-NH-1,2,3-triazoles has been developed. p-TsOH was discovered as a vital additive in this type of 1,3-dipolar cycloaddition This novel cycloaddition reaction is a good method for the rapid synthesis of valuable 4-aryl-NH-1,2,3-triazoles in high yields.

Organic Letters published new progress about 5153-73-1. 5153-73-1 belongs to nitriles-buliding-blocks, auxiliary class Nitrile,Alkenyl,Nitro Compound,Benzene, name is (E)-4-(2-Nitrovinyl)benzonitrile, and the molecular formula is C9H6N2O2, Safety of (E)-4-(2-Nitrovinyl)benzonitrile.

Referemce:
https://en.wikipedia.org/wiki/Nitrile,
Nitriles – Chemistry LibreTexts