Category: 5153-73-1

Wang, Jian-Shu published the artcileEx Situ Generation of Difluorodiazoethane (CF₂HCHN₂): Application in the Regioselective Synthesis of CF₂H-Containing Pyrazoles, HPLC of Formula: 5153-73-1, the publication is Organic Letters (2019), 21(21), 8751-8755, database is CAplus and MEDLINE.

A new method for the ex situ generation of difluorodiazoethane (CF₂HCHN₂) and a procedure for its efficient use in [3 + 2] cycloaddition with nitroolefins by the AcOH/O₂ catalyst system were developed by using a simple two-chamber system. The method provides a facile and straightforward access to a series of 4-substituted 5-difluoromethyl-3-nitro-1H-pyrazoles that are of interest in medicinal chem. Interestingly, the key factor for the success of this method is the efficient preparation of CF₂HCHN₂ by an ex situ process.

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 C8H7N3, HPLC of Formula: 5153-73-1.

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

Dou, Xiaowei published the artcileFrom the Feist-Benary reaction to organocatalytic domino Michael-alkylation reactions: asymmetric synthesis of 3(2 H)-furanones, Recommanded Product: (E)-4-(2-Nitrovinyl)benzonitrile, the publication is Chemistry – A European Journal (2012), 18(1), 85-89, S85/1-S85/45, database is CAplus and MEDLINE.

A modified Feist-Benary reaction by employing a domino Michael-alkylation sequence for the enantioselective preparation of 3(2H)-furanones is introduced. A L-threonine-derived tertiary amine/thiourea catalyst was synthesized to promote the domino Michael-alkylation reaction efficiently, affording the title compounds in high yields and excellent enantioselectivities.

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, Recommanded Product: (E)-4-(2-Nitrovinyl)benzonitrile.

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

Rani, Dixita published the artcileAqueous synthesis of 2-aryl-3-nitro-2H-chromenes via L-prolinamide mediated tandem oxa-Michael Henry reactions, Category: nitriles-buliding-blocks, the publication is Journal of Molecular Structure (2022), 133341, database is CAplus.

An efficient and aqueous protocol was developed for the synthesis of 2-aryl-3-nitro-2H-chromene derivatives This protocol involves the L-prolinamide mediated tandem oxa-Michael Henry reaction between a variety of β-nitrostyrenes and salicylaldehyde. Among the screened solvents, the catalytic efficiency of prolinamides was found to be high in chloroform, but the best results were obtained in water to provide the 2-phenyl-3-nitro-2H-chromene in excellent yields. Substrate scope was also investigated using various substituted β-Nitrostyrenes. All reactions worked well to provide the corresponding products in very high yields. Theor. calculations were performed to find out the reaction pathways and nature of transition state at 3-21G* basis set and TS1 corresponding to the product (S)-3a, was found favorable by 1.13 kcal/mol over TS2 corresponding to the product (R)-3a.

Journal of Molecular Structure 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

Wang, Hai-Jun published the artcilePd/C-Catalyzed Dehydrogenative [3+2] Cycloaddition for the Synthesis of Functionalized Tropanes, Name: (E)-4-(2-Nitrovinyl)benzonitrile, the publication is European Journal of Organic Chemistry (2018), 2018(39), 5456-5459, database is CAplus.

A Pd/C-catalyzed cascade approach for the synthesis of attractive benzo-fused tropanes was developed. The reaction proceeds through a sequential Pd/C-catalyzed dehydrogenative formation of azomethine ylides from amines and 1,3-dipolar cycloaddition It gave structurally complex benzo-fused tropanes in good yields with excellent diastereoselectivities under mild reaction conditions. Preliminary results of asym. version of the reaction reveal that the copper catalyst and chiral monophosphoramidite ligand can furnish optically active products with moderate ee.

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 C6H5BFNO4, Name: (E)-4-(2-Nitrovinyl)benzonitrile.

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

Trost, Barry M. published the artcileHighly Stereoselective Synthesis of α-Alkyl-α-Hydroxycarboxylic Acid Derivatives Catalyzed by a Dinuclear Zinc Complex, Formula: C9H6N2O2, the publication is Angewandte Chemie, International Edition (2012), 51(26), 6480-6483, S6480/1-S6480/101, database is CAplus and MEDLINE.

The authors describe a highly diastereo- and enantioselective nitro-Michael reaction of 5H-oxazol-4-ones. The process provides a range of highly functionalized α-alkyl-α-hydroxycarboxylic acid derivatives in high yields. For example, reacting β-nitrostyrene with methyloxazolone I gave the desired product II in 95% yield (d.r. = 15.6:1, 88% ee) in the presence of ZnEt₂ and phenol ligand III.

Angewandte Chemie, International Edition 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 C30H24BrCuN2P, Formula: C9H6N2O2.

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

Li, Si-Yuan published the artcilePractical copper-catalyzed chloronitration of alkenes with TMSCl and guanidine nitrate, Quality Control of 5153-73-1, the publication is Organic Chemistry Frontiers (2020), 7(17), 2449-2455, database is CAplus.

A novel and practical chloronitration of alkenes in the presence of easily available TMSCl and guanidine nitrate was developed by using cheap copper sulfate pentahydrate as the catalyst. A variety of vic-chloronitro compounds were directly synthesized in good to excellent yields on up to 100 mmol scale under mild reaction conditions, and the resulting products could be smoothly transformed into the corresponding nitroalkenes and diverse nitro compounds bearing a vicinal nucleophilic “C”, “N” or “S” unit.

Organic Chemistry Frontiers 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

Shan, Xiaojie published the artcile2,2′-Azodi(2-methylbutyronitrile) (AMBN) Promoted Alkenylation of Cyclic Ethers via Radical Addition to β-Nitrostyrenes, Recommanded Product: (E)-4-(2-Nitrovinyl)benzonitrile, the publication is ChemistrySelect (2022), 7(13), e202200425, database is CAplus.

It is reported the alkenylation of cyclic ethers via radical addition to β-nitrostyrenes in the presence of AMBN without any other additives under mild conditions. A wide range of β-nitrostyrenes and various ethers are tested in this reaction, most cases are happed smoothly with excellent to good yields. Cyclohexane also could be reacted under the conditions with moderate yield. According to the control experiments, the reaction mechanism was proposed. It is found that AMBN could induce to hydrogen abstraction from sp³ carbon under oxygen atm. This reaction system possesses the advantages of very high reactivity, stability, and convenient preparation method. Especially, it is very useful in the pharmacy industry due to the metal-free and easy treatment conditions.

ChemistrySelect 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 C15H21BO2, Recommanded Product: (E)-4-(2-Nitrovinyl)benzonitrile.

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

Chen, Weiqiang published the artcileThe Cyclohexa-2,5-dienyl Group as a Placeholder for Hydrogen: Organocatalytic Michael Addition of an Acetaldehyde Surrogate, SDS of cas: 5153-73-1, the publication is Chemistry – A European Journal (2020), 26(66), 15126-15129, database is CAplus and MEDLINE.

An aldehyde with a cyclohexa-2,5-dienyl group in the α-position is introduced as a storable surrogate of highly reactive acetaldehyde. The cyclohexa-2,5-dienyl unit is compatible with an enantioselective Michael addition to nitroalkenes promoted by a Hayashi-Jorgensen catalyst and can be removed by a boron Lewis acid mediated C-C bond cleavage. The robust two-step sequence does not require a large excess of the aldehyde component that is typically needed when directly using acetaldehyde.

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, SDS of cas: 5153-73-1.

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

Izquierdo, Joseba published the artcileEnantioselective Synthesis of 5,5-Disubstituted Hydantoins by Bronsted Base/H-Bond Catalyst Assisted Michael Reactions of a Design Template, Safety of (E)-4-(2-Nitrovinyl)benzonitrile, the publication is Chemistry – A European Journal (2018), 24(28), 7217-7227, database is CAplus and MEDLINE.

A new method for the enantioselective synthesis of 5,5-disubstituted (quaternary) hydantoins, e.g., I was developed on the basis of an organocatalytic Michael reaction approach involving the use of 2-benzylthio-3,5-dihydroimidazol-4-ones as key hydantoin surrogates. The method is general with respect to the substitution pattern at the hydantoin N¹ (alkyl, aryl, acyl), N³ (aryl), and C⁵ (linear/branched alkyl, aryl) positions and affords essentially single diastereomeric products with enantioselectivities higher than 95 % ee in most cases. Among the bifunctional Bronsted base/H-bond catalysts examined, a known squaramide-tertiary amine catalyst II and a newly prepared squaramide-tertiary amine catalyst III provide the highest selectivity so far with either nitroolefins or vinyl ketones as the acceptor components. Kinetic measurements support a first-order rate dependence on both reaction partners, the donor template and the Michael acceptor, whereas competitive ¹H NMR spectroscopy experiments reveal the high ability of the template for catalyst binding.

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

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

Diosdado, Saioa published the artcileCatalytic Enantioselective Synthesis of Tertiary Thiols From 5H-Thiazol-4-ones and Nitroolefins: Bifunctional Ureidopeptide-Based Bronsted Base Catalysis, Computed Properties of 5153-73-1, the publication is Angewandte Chemie, International Edition (2013), 52(45), 11846-11851, database is CAplus and MEDLINE.

The synthesis of the target compounds was achieved using urea-peptide analogs as catalysts (Bronsted acids). A reaction of amino acids (L-valine, 3-methyl-L-valine) with (8α,9S)-6′-methoxycinchonan-9-amine (epiquinine, cinchona alkaloid derivative) provided the above-mentioned urea-peptide analogs. These catalysts were applied in a Michael reaction of thiazolone derivatives with (nitro)alkenes. A reaction of 2-mercaptobutanoic acid, 2-(mercapto)octanoic acid, α-(mercapto)benzenepropanoic acid with nitriles provided 4-thiazolol derivatives (4-thiazolone derivatives). The title compounds thus formed included a thiazolone nitroalkane derivative (I) and related substances, quinoline derivatives, naphthalene derivatives, etc.

Angewandte Chemie, International Edition 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