Category: 5153-73-1

Maripally, Narsimulu published the artcileDMAP catalyzed addition-cyclization reaction of 2-hydroxyphenyl-para-quinone methide with nitroalkenes: facile entry into highly substituted chromane derivatives, SDS of cas: 5153-73-1, the publication is Tetrahedron Letters (2020), 61(9), 151554, database is CAplus.

The base catalyzed reaction of 2-hydroxyphenyl-para-quinone methide (p-QM) with nitroalkenes was reported. The DMAP-catalyzed reaction afforded substituted chromane derivatives I [R = H, 7-Me, 6-MeO, 6-F, 6-Cl, 6-Br; R¹ = i-Bu, Ph, 2-thienyl, etc.; stereo = R or S] in excellent yields with moderate diastereoselectivity. The conversion of the initial products to other useful structures was also achieved.

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

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

Zhu, Yadong published the artcileOrganocatalytic enantioselective Michael addition of cyclic hemiacetals to nitroolefins: a facile access to chiral substituted 5- and 6-membered cyclic ethers, Application of (E)-4-(2-Nitrovinyl)benzonitrile, the publication is Organic & Biomolecular Chemistry (2015), 13(16), 4769-4775, database is CAplus and MEDLINE.

An efficient aminocatalytic enantioselective Michael addition of readily available cyclic hemiacetals to nitroolefins has been developed. The strategy serves as a powerful approach to synthetically valuable chiral 3-substituted tetrahydrofurans (THFs) I [R = Et, Ph, 3-NO₂-C₆H₄, etc.] and tetrahydropyrans (THPs) II. The synthetic utilities of the versatile Michael adducts also have been demonstrated in the synthesis of 2,3-disubstituted cyclic ethers, α-substituted lactones and venlafaxine analogs.

Organic & Biomolecular 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 C11H15NO2, Application of (E)-4-(2-Nitrovinyl)benzonitrile.

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

Rokade, Balaji V. published the artcileSynthesis of substituted nitroolefins: a copper catalyzed nitrodecarboxylation of unsaturated carboxylic acids, COA of Formula: C9H6N2O2, the publication is Organic & Biomolecular Chemistry (2013), 11(39), 6713-6716, database is CAplus and MEDLINE.

A novel, mild and convenient method for the nitrodecarboxylation of substituted cinnamic acid derivatives to their nitroolefins is achieved using a catalytic amount of CuCl (10 mol%) and tert-Bu nitrite (2 equivalent) as a nitrating agent in the presence of air. This reaction provides a useful method for the synthesis of β,β-disubstituted nitroolefin derivatives, which are generally difficult to access from other conventional methods. Addnl., this reaction is selective as the E-isomer of the acid derivatives furnishes the corresponding E-nitroolefins. One more salient feature of the method is, unlike other methods, no metal nitrates or HNO₃ are employed for the transformation.

Organic & Biomolecular 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, COA of Formula: C9H6N2O2.

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

Hara, Momoko published the artcileNoncovalent Modification Strategy with Achiral Phosphoric Acid Diesters for Designing a Chiral Bronsted Base Organocatalyst, Product Details of C9H6N2O2, the publication is Bulletin of the Chemical Society of Japan (2022), 95(4), 553-555, database is CAplus.

A strategy for designing chiral Bronsted base organocatalysts through noncovalent modification of a chiral dibasic mol. with an achiral phosphoric acid diester is introduced for the first time. Such a mol. modification concept utilizing acid-base interactions may facilitate the on-demand design of asym. organocatalysts, as preliminarily demonstrated in this work.

Bulletin of the Chemical Society of Japan 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, Product Details of C9H6N2O2.

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

Maity, Soham published the artcileStereoselective Nitration of Olefins with ^tBuONO and TEMPO: Direct Access to Nitroolefins under Metal-free Conditions, Application of (E)-4-(2-Nitrovinyl)benzonitrile, the publication is Organic Letters (2013), 15(13), 3384-3387, database is CAplus and MEDLINE.

Nitroolefins are essential elements for both synthetic chem. and medicinal research. Despite significant improvements in nitration of olefin an efficient metal-free synthesis remains elusive so far. Herein, we disclose a new set of reagents to access nitroolefins in a single step under metal-free conditions. A wide range of olefins with diverse functionalities has been nitrated in synthetically useful yields. This transformation is operationally simple and exhibits excellent E-selectivity. Furthermore, site selective nitration in a complex setup makes this method advantageous.

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

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

Dianati, Vahid published the artcileImproving the Selectivity of PACE4 Inhibitors through Modifications of the P1 Residue, Application In Synthesis of 5153-73-1, the publication is Journal of Medicinal Chemistry (2018), 61(24), 11250-11260, database is CAplus and MEDLINE.

Paired basic amino acid cleaving enzyme 4 (PACE4), a serine endoprotease of the proprotein convertases family, has been recognized as a promising target for prostate cancer. We previously reported a selective and potent peptide-based inhibitor for PACE4, named the multi-Leu peptide (Ac-LLLLRVKR-NH₂ sequence), which was then modified into a more potent and stable compound named C23 with the following structure: Ac-DLeu-LLLRVK-Amba (Amba: 4-amidinobenzylamide). Despite improvements in both in vitro and in vivo profiles of C23, its selectivity for PACE4 over furin was significantly reduced. We examined other Arg-mimetics instead of Amba to regain the lost selectivity. Our results indicated that the replacement of Amba with 5-(aminomethyl)picolinimidamide increased affinity for PACE4 and restored selectivity. Our results also provide a better insight on how structural differences between S1 pockets of PACE4 and furin could be employed in the rational design of selective 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 In Synthesis of 5153-73-1.

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

Tang, Ren-Jin published the artcileFriedel-Crafts alkylation reaction with fluorinated alcohols as hydrogen-bond donors and solvents, Application of (E)-4-(2-Nitrovinyl)benzonitrile, the publication is RSC Advances (2018), 8(19), 10314-10317, database is CAplus and MEDLINE.

An effective and clean Friedel-Crafts alkylation of indoles and electron-rich arenes with β-nitroalkenes in hexafluoroisopropanol is reported. The desired products were formed rapidly in excellent yields under mild conditions without the need for any addnl. catalysts or reagents. Further, this methodol. could be applied to one-pot synthesis of biol. active tryptamine derivatives

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 C6H12Br2, Application of (E)-4-(2-Nitrovinyl)benzonitrile.

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

Kiyokawa, Kensuke published the artcileStraightforward Synthesis of 1,2-Dicyanoalkanes from Nitroalkenes and Silyl Cyanide Mediated by Tetrabutylammonium Fluoride, Computed Properties of 5153-73-1, the publication is Chemistry – A European Journal (2015), 21(3), 1280-1285, database is CAplus and MEDLINE.

A straightforward synthesis of 1,2-dicyanoalkanes RCH(CN)CH(R¹)CN [R = 4-OCH₃C₆H₄, thiophen-2-yl, pyridin-3-yl, etc.; R¹ = H; RR¹ = (CH₂)₄] by reacting nitroalkenes with trimethylsilyl cyanide in the presence of tetrabutylammonium fluoride was described. The reaction proceeds through a tandem double Michael addition under mild conditions. Employing the hypervalent silicate generated from trimethylsilyl cyanide and tetrabutylammonium fluoride was essential for achieving this transformation. Mechanistic studies suggest that a small amount of water included in the reaction media plays a key role. This protocol was applicable to various types of substrates including electron-rich and electron-deficient aromatic nitroalkenes and aliphatic nitroalkenes. Moreover, vinyl sulfones were found to be good alternatives, particularly for electron-deficient nitroalkenes. The broad substrate scope and functional group tolerance of the reaction makes this approach a practical method for the synthesis of valuable 1,2-dicyanoalkanes RCH(CN)CH(R¹)CN.

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 C9H6N2O2, Computed Properties of 5153-73-1.

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

Kashanna, Jajula published the artcilePalladium catalyzed carboannulation of nitrostyrenes with internal alkynes: a new synthetic strategy for cross coupling/C-H annulation and facile access to indenones, Application In Synthesis of 5153-73-1, the publication is Tetrahedron Letters (2016), 57(14), 1576-1581, database is CAplus.

Palladium(II) catalyzed carboannulation reaction of internal alkynes with nitrostyrenes to afford 2,3-disubstituted indenones is reported. The annulation reaction proceeds through transmetalation of Pd(II) with aldehydes generated from the nitrostyrene (C-H activation) and insertion of the alkynes, followed by cyclization via intramol. nucleophilic addition of intermediate organopalladium(II) species. This reaction proceeded in moderate to good yields and with high regioselectivity. Electron-rich nitrostyrenes were transformed to the corresponding aldehydes in high yields without addition of any peroxide reagent.

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

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

Guo, Shuhui published the artcileTetraarylphosphonium inner-salts (TAPIS) as both Lewis base catalyst and phase tag, Name: (E)-4-(2-Nitrovinyl)benzonitrile, the publication is Tetrahedron Letters (2017), 58(30), 2881-2884, database is CAplus.

Tetraarylphosphonium inner-salts (TAPIS) were designed, synthesized and verified as recyclable and reusable Lewis base catalysts. The resulted TAPIS catalyst was successfully applied in Michael addition, cyanation and trifluoromethylation reactions.

Tetrahedron 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