Category: 5153-73-1

Zhou, Meng published the artcileA Metal-Free Three-Component Reaction of trans-β-Nitrostyrene Derivatives, Dibromo Amides, and Amines Leading to Functionalized Amidines, COA of Formula: C9H6N2O2, the publication is Journal of Organic Chemistry (2019), 84(2), 1015-1024, database is CAplus and MEDLINE.

Amidines such as I were prepared chemoselectively and diastereoselectively by three-component reactions of β-nitrostyrenes such as (E)-PhCH:CHNO₂ with BocNBr₂ or with N,N-dibromoamides generated in situ from amides and N-bromosuccinimide or N-chlorosuccinimide. A bisamidine and α,β-unsaturated amidines were prepared using this method. The mechanism of formation of I was studied by isolation of reaction intermediates and their further reaction; the α,α-dibromonitroalkane PhCH(NHBoc)CBr₂NO₂ [formed by addition of BocNBr₂ to (E)-PhCH:CHNO₂] underwent elimination to (Z)-PhC(NHBoc):CBrNO₂ which underwent C-C bond cleavage in the presence of base and morpholine to yield I.

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 C8H6ClNO, COA of Formula: C9H6N2O2.

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

Ng, Wing-Hin published the artcileZwitterion-Catalyzed Amino-Dibromination of Nitroalkenes: Scope, Mechanism and Application to The Synthesis of Glycinamides, HPLC of Formula: 5153-73-1, the publication is Asian Journal of Organic Chemistry (2021), 10(5), 1131-1140, database is CAplus.

Herein, a zwitterion-catalyzed aminobromination of nitroalkenes using N-bromosuccinimide as the Br source and the amide donor was reported. The resulting aminobromide products were converted into glycinamides.

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, HPLC of Formula: 5153-73-1.

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

Gallardo-Fuentes, Sebastian published the artcileInfluence of Non-Covalent Interactions in the Exo- and Regioselectivity of Aza-Diels-Alder Reactions: Experimental and DFT Calculations, Application In Synthesis of 5153-73-1, the publication is Journal of Organic Chemistry (2019), 84(17), 10825-10831, database is CAplus and MEDLINE.

A systematic exptl. and theor. study of the intermol. aza-Diels-Alder reaction using 5-aminopyrrole as a building block shows that the commonly accepted endo selectivity, ruled by controversial secondary orbital interactions, are overcome by non-covalent interactions affording the unusual exo adduct. Addnl., the regioselectivity is also influenced by such interactions. The starting materials are easily prepared, and the use of water as the solvent is a great achievement for the development of cleaner synthetic methodologies.

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, Application In Synthesis of 5153-73-1.

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

Dianati, Vahid published the artcileIncreasing C-Terminal Hydrophobicity Improves the Cell Permeability and Antiproliferative Activity of PACE4 Inhibitors against Prostate Cancer Cell Lines, Application of (E)-4-(2-Nitrovinyl)benzonitrile, the publication is Journal of Medicinal Chemistry (2018), 61(18), 8457-8467, database is CAplus and MEDLINE.

The serine protease, PACE4, is a proprotein convertase that plays a substantial role in malignancy of prostate cancer. Our initial selective PACE4 inhibitor (Ac-LLLLRVKR-NH₂) has evolved to the current lead compound C23 (Ac-DLeu-LLLRVK-Amba), which is active both in vitro and in vivo. By screening natural residues, except Cys, in C-terminal P1′ position, it was established that increasing hydrophobicity was improving cell permeability, which was directly translated into PCa cells antiproliferative activity. This cell antiproliferation enhancement seems independent from effect of P1′ residue on PACE4 affinity. Replacement of P1-Amba of C23 by Acpa ((S)-2-amino-3-(4-carbamimidoylphenyl)propanoic acid) followed by addition of tryptamine in P1′ resulted in compound 32 exhibiting superior PCa cells antiproliferative activity over the reference compound C23 (3-fold). This study sheds light on key factors that improve cell penetrating property and antiproliferative activity of PACE4 inhibitors.

Journal of Medicinal 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, Application of (E)-4-(2-Nitrovinyl)benzonitrile.

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

Sekikawa, Tohru published the artcileCatalytic Activity of epi-Quinine-Derived 3,5-Bis(trifluoromethyl)benzamide in Asymmetric Nitro-Michael Reaction of Furanones, SDS of cas: 5153-73-1, the publication is Organic Letters (2015), 17(12), 3026-3029, database is CAplus and MEDLINE.

High catalytic activity of novel epi-quinine-derived 3,5-bis(CF₃)benzamide in the asym. nitro-Michael reaction is described. With 0.1-5 mol % loadings of this catalyst, the addition of 5-substituted 2(3-H)-furanones to a wide range of nitroalkenes involving challenging substrates, β-alkylnitroalkenes, smoothly proceeded, giving the Michael adducts e. g., I, in high yields (>90%) with excellent diastereo- and enantioselectivity (>98:2 dr, syn major; 88-98% ee). DFT calculation was carried out to account for the high catalytic activity.

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 C30H32ClN7O2, SDS of cas: 5153-73-1.

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

Xiao, Yuanyuan published the artcileEnantioselective Construction of Spiro Thiazol-4-one Derivatives with Multiple Stereocenters via an Organocatalyzed Multicomponent Cascade Reaction, Computed Properties of 5153-73-1, the publication is Advanced Synthesis & Catalysis (2018), 360(10), 1961-1966, database is CAplus.

An organocatalyzed asym. three-component reaction of thiazol-4-ones, acrolein and nitroolefins, which provides an efficient approach to access optically active spiro thiazol-4-ones I (R = C₆H₅, 4-FC₆H₄, 4-F₃CC₆H₄, etc.; R¹ = C₆H₅, 1-naphthyl, 2-thienyl, etc.) is developed. Under the catalysis of a bifunctional squaramide derived from L-tert-leucine, the reactions of a wide range of thiazol-4-ones, acrolein and nitroolefins took place smoothly to generate the corresponding spirothiazolone derivatives bearing four contiguous stereogenic centers in good yields with high levels of enantioselectivity. The title chiral spirothiazolones were obtained as a pair of separable epimers, which are formed through a double Michael addition followed by a Henry process.

Advanced Synthesis & Catalysis 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 C4H3Cl2N3, Computed Properties of 5153-73-1.

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

Zhang, Kun published the artcileSynthetic Diversity from a Versatile and Radical Nitrating Reagent, Quality Control of 5153-73-1, the publication is Chemistry – A European Journal (2019), 25(56), 12929-12939, database is CAplus and MEDLINE.

A new methodol. was described for the activation of N-nitrosuccimide for the direct synthesis of β-nitroalkenes, β-nitrohydrins, β-nitroethers, isoxazolines I [R = Me, cyclopropyl; R¹ = n-heptyl, Bn, CH₂OPh; R² = H, R¹R² = (CH₂)₄, (CH₂)₉, (CH₂)₁₀C(O)(CH₂)₃; R³ = H, Me] and isoxazoles II [R⁴ = CO₂Et, CH₂CH₂Br, cyclohexyl, etc.]. Detailed mechanistic studies strongly suggested that a mesolytic N-N bond fragmentation liberates a nitryl radical. Using in situ photo-sensitized, ESR spectroscopy, direct evidence of a nitryl radical in solution by nitrone spin-trapping was observed To further exhibit versatility of N-nitrosuccinimide under photoredox conditions, the late-stage diversification of an extensive number of C-H partners to prepare isoxazolines I and isoxazoles II was presented. This approach allowed for the formation of an in situ nitrile oxide from a ketone partner, the presence of which was detected by the formation of the corresponding furoxan when conducted in the absence of a dipolarophile. This 1,3-dipolar cycloaddition with nitrile oxides and alkenes or alkynes proceeded in a single-operational step using a mild, regioselective and general protocol with broad chemoselectivity.

Chemistry – A European Journal 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 C12H10N2O5, Quality Control of 5153-73-1.

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

Manna, Srimanta published the artcileSynthesis of (E)-nitroolefins via decarboxylative nitration using t-butylnitrite (t-BuONO) and TEMPO, SDS of cas: 5153-73-1, the publication is Chemical Communications (Cambridge, United Kingdom) (2013), 49(46), 5286-5288, database is CAplus and MEDLINE.

Nitroolefins are usually synthesized using the Henry reaction. Here, the authors report an alternative metal-free decarboxylative nitration protocol for the preparation of the nitroolefins from α,β-unsaturated carboxylic acids using tert-butylnitrite (t-BuONO) and TEMPO. α,β-Unsaturated carboxylic acids bearing β-aromatic and β-heteroaromatic substituents gave (E)-nitroolefins exclusively under mild conditions. A radical based pathway has been proposed for this decarboxylative nitration reaction.

Chemical Communications (Cambridge, United Kingdom) 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

Han, Xinya published the artcileBiological evaluation and SAR analysis of novel covalent inhibitors against fructose-1,6-bisphosphatase, Formula: C9H6N2O2, the publication is Bioorganic & Medicinal Chemistry (2020), 28(18), 115624, database is CAplus and MEDLINE.

Herein, a series of nitrostyrene derivatives I (R¹ = H, F, Me, etc.; R² = H, Cl, Me, etc.; R³ = H, Cl, Br, Me) were synthesized, and their inhibitory activities against Fructose-1,6-bisphosphatase (FBPase) were investigated in vitro. Most of the prepared compounds exhibit potent FBPase inhibition (IC₅₀ < 10μM). Specifically, when the substituents of F, Cl, OMe, CF₃, OH, CO₂H, or 2-nitrovinyl were installed at the R² (meta-) position of the benzene ring, the FBPase inhibitory activities of the resulting compounds increased 4.5-55 folds compared to those compounds with the same groups at the R¹ (para-) position. In addition, the preferred substituents at the R³ position were Cl or Br, thus compound I (R¹ = NO₂; R² = H; R³ = Cl) exhibited the most potent inhibitory activity (IC₅₀ = 0.15μM). The mol. docking and site-directed mutation suggest that C128 and N125 are essential for the binding of I (R¹ = NO₂; R² = H; R³ = Cl) and FBPase, which is consistent with the C128-N125-S123 allosteric inhibition mechanism. The reaction enthalpy calculations show that the order of the reactions of compounds with thiol groups at the R³ position is Cl > H > CH₃. CoMSIA anal. is consistent with proposed binding mode. The effect of compounds I (R¹ = 1,2,4-triazol-1-yl; R² = H; R³ = H) and I (R¹ = NO₂; R² = H; R³ = Cl) on glucose production in primary mouse hepatocytes were further evaluated, showing that the inhibition was 71% and 41% at 100μM, resp.

Bioorganic & Medicinal 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, Formula: C9H6N2O2.

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

Zheng, Changge published the artcileGeometrically Selective Denitrative Trifluoromethylthiolation of β-Nitrostyrenes with AgSCF₃ for (E)-Vinyl Trifluoromethyl Thioethers, Application In Synthesis of 5153-73-1, the publication is Organic Letters (2020), 22(12), 4868-4872, database is CAplus and MEDLINE.

An efficient copper(II)-promoted denitrative trifluoromethylthiolation under mild reaction conditions has been developed for vinyl trifluoromethyl thioethers to construct C_vinyl-SCF₃ bonds with stable AgSCF₃ as a source of the trifluoromethylthio. This reaction system tolerates a broad range of functional groups to commendably achieve a high product yield and excellent stereoselectivity of E/Z.

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 C24H29N5O3, Application In Synthesis of 5153-73-1.

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