Category: 5153-73-1

Cui, Bao-Dong published the artcile3-Pyrrolyl-oxindoles as efficient nucleophiles for organocatalytic asymmetric synthesis of structurally diverse 3,3′-disubstituted oxindole derivatives, Application of (E)-4-(2-Nitrovinyl)benzonitrile, the publication is Chemical Communications (Cambridge, United Kingdom) (2015), 51(4), 757-760, database is CAplus and MEDLINE.

A range of 3-pyrrolyl-3,3′-disubstituted oxindoles, e.g., I, were smoothly obtained via the reaction of 3-pyrrolyl-oxindoles with nitroalkenes using an organocatalyst. The usefulness of the protocol was also demonstrated by the versatile conversions of the Michael adducts into other functionalized 3,3′-disubstituted oxindoles, as well as into the analogs of some valuable natural products.

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

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

Cai, Pin-Wen published the artcileThe Attractive Application of Lactol Chemistry: From Racemic Lactol to Natural Product Skeleton, Related Products of nitriles-buliding-blocks, the publication is Synthesis (2016), 48(16), 2581-2594, database is CAplus.

A versatile methodol. involving the use of substituted racemic lactols as nucleophiles in the enamine-based asym. reactions leading to functionalized lactones with multiple stereogenic centers as one single diastereoisomer is reported. Importantly, the desired products could be easily transformed into asym. 2,4,5-trisubstituted piperidine derivatives (e.g. I), which are present in numerous alkaloid products but difficult to prepare optically enriched. Moreover, although starting from racemic precursors, the stereoisomeric products were discretely provided by simple column chromatog., which could meet the requirements of atom economy and efficiency.

Synthesis 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, Related Products of nitriles-buliding-blocks.

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

Fuchs, Patrick J. W. published the artcileAn N-Heterocyclic Carbene-Mediated, Enantioselective and Multicatalytic Strategy to Access Dihydropyranones in a Sequential Three-Component One-Pot Reaction, SDS of cas: 5153-73-1, the publication is Organic Letters (2017), 19(22), 6076-6079, database is CAplus and MEDLINE.

The multicatalytic generation of 3,5,6-trisubstituted 3,4-dihydropyranones with high enantioselectivity using a highly convergent strategy starting from com. available precursors is reported. The operationally simple three-step, one-pot protocol merges H-bond and NHC catalysis to provide crucial, reactive β-unsubstituted enones from nitroalkenes as latent 1,2-biselectrophiles. These intermediates are directly funneled into a further NHC-catalyzed formal hetero-Diels-Alder reaction to deliver manifold chiral C(4)-unsubstituted dihydropyranones (typical ee >98%), allowing aliphatic and heteroaromatic substituents and hence expanding the scope of this Michael addition/lactonization.

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, SDS of cas: 5153-73-1.

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

Bai, Zhushuang published the artcileA vinylogous Michael reaction of 2-furanone dimers with α,β-unsaturated nitroolefins for constructing chiral γ,γ-disubstituted butenolides, Synthetic Route of 5153-73-1, the publication is Organic Chemistry Frontiers (2020), 7(19), 2910-2915, database is CAplus.

An efficient bifunctional thiourea-catalyzed asym. vinylogous Michael addition of 2-furanone dimers to α,β-unsaturated nitroolefins was developed to afford functional chiral γ,γ-disubstituted butenolides I [R¹ = i-Pr, 2-furyl, Ph, etc.; R² = Me, Et, n-Pr; R³ = Me, Et] in good yields (up to 95%) with good to excellent stereoselectivity (up to >20:1 dr, 99% ee). DFT calculations were carried out to explain the high stereoselectivity.

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, Synthetic Route of 5153-73-1.

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

Biswas, Soumen published the artcileDiastereoselective pot- and atom-economical synthesis of densely-substituted polycyclic 1,2- and 1,2,3-fused indole scaffolds, Application of (E)-4-(2-Nitrovinyl)benzonitrile, the publication is Tetrahedron Letters (2019), 60(32), 150921, database is CAplus.

A simple, efficient, one-pot sequential process for the preparation of a family of 8,9-dihydropyrido[1,2-a]indol-6(7H)-one scaffolds I [R¹ = Ph, 2-ClC₆H₄, 2-furyl, etc.; stereo = cis, trans] in acceptable yields was established under mild conditions. The Michael-hemiaminalization-oxidation reaction proceeded between Me 2-(3-formyl-1H-indol-2-yl) acetate and trans-β-aryl/alkyl-substituted acroleins using pyrrolidine-BzOH as an efficient organocatalyst, followed by oxidation of in situ generated of C,N-fused hemiaminal adducts in the presence of PDC at room temperature Excitingly, organobase-catalyzed highly diastereoselective (up to ≤9:1 dr) construction of a series of pharmacol. attractive 1,2,3-fused tetracyclic indole scaffolds with five contiguous chiral centers including an all-carbon stereogenic center II [R² = CO₂Me, Ph, 2-furyl, etc.; R³ = Ph, 4-MeOC₆H₄] was achieved using developed method. Moreover, pyrrolidine-BzOH and PTSA as combined catalytic systems promoted the uninterrupted sequential Michael-cyclization reaction, followed by N-alkylation reaction with carbazole to produce interesting class of 6-(9H-carbazol-9-yl)-6,7,8,9-tetrahydropyrido[1,2-a]indole derivatives III [R³ = Ph, 4-MeOC₆H₄] in a diastereoselective manner.

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

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

Sun, Minzhi published the artcileFree-Radical-Promoted Alkenylation of C(sp³)-H Bond in Chloroalkane with Cinnamic Acid and β-Nitrostyrene, Formula: C9H6N2O2, the publication is Advanced Synthesis & Catalysis (2020), 362(11), 2195-2199, database is CAplus.

Herein a free-radical alkenylation of the C(sp³)-H bond in 1,2-dichloroethane with cinnamic acid and β-nitrostyrene has been demonstrated. This method not only provides a facile approach to chloroalkylated styrenes, but also would be instructive for halogen-atom directing selective functionalization of inert C(sp³)-H bond.

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 C11H12O4, Formula: C9H6N2O2.

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

Corbett, Michael T. published the artcileTrisubstituted 2-Trifluoromethyl Pyrrolidines via Catalytic Asymmetric Michael Addition/Reductive Cyclization, Quality Control of 5153-73-1, the publication is Organic Letters (2014), 16(9), 2362-2365, database is CAplus and MEDLINE.

The stereoselective synthesis of trisubstituted 2-trifluoromethyl pyrrolidines by asym. Michael addition/hydrogenative cyclization is described. The direct organocatalytic addition of 1,1,1-trifluoromethyl ketones to nitroolefins proceeds under mild reaction conditions and low catalyst loadings to provide Michael adducts in high yield with excellent diastereo- and enantioselectivity. Catalytic hydrogenation of the Michael adducts stereoselectively generates 2-trifluoromethylated pyrrolidines bearing three contiguous stereocenters. A stereospecific route to epimeric 2-trifluoromethyl pyrrolidines from a common intermediate is described.

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, Quality Control of 5153-73-1.

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

Chen, Xiang-Yu published the artcileCatalytic MBH reaction of β-substituted nitroalkenes with azodicarboxylates, Name: (E)-4-(2-Nitrovinyl)benzonitrile, the publication is Organic & Biomolecular Chemistry (2013), 11(34), 5722-5726, database is CAplus and MEDLINE.

An unprecedented N-heterocyclic carbene (NHC) catalyzed Morita-Baylis-Hillman (MBH) reaction of β-substituted nitroalkenes and azodicarboxylates has been developed. Both β-aryl and β-alkyl nitroalkenes worked well for the reaction using 5 mol% of NHC catalyst, giving the desired α-hydrazino-α,β-unsaturated nitroalkenes in good to excellent yields. E.g., in presence of NHC catalyst (I) and DMAP, Morita-Baylis-Hillman reaction of (E)-PhCH:CHNO₂ and DEAD gave 91% II.

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

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

Saha, Arijit published the artcileFacile Synthesis of 1,3,5-Triarylbenzenes and 4-Aryl-NH-1,2,3-Triazoles Using Mesoporous Pd-MCM-41 as Reusable Catalyst, Related Products of nitriles-buliding-blocks, the publication is European Journal of Organic Chemistry (2019), 2019(1), 104-111, database is CAplus.

We report mesoporous nano-Pd-MCM-41 catalyzed rapid and efficient synthesis of 1,3,5-triarylbenzenes via de-nitrative cyclotrimerization of β-nitrostyrenes. All the reactions were very fast and high yielding. The Pd-MCM-41 was also very effective in catalyzing de-nitrative [3+2] cycloaddition of β-nitrostyrenes with TMSN₃ to synthesize 4-aryl-NH-1,2,3-triazoles. The catalyst was reused at least up to eight times with min. loss of catalytic activity.

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, Related Products of nitriles-buliding-blocks.

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

Chen, Chen published the artcileDiastereo- and Enantioselective Synthesis of Functionalized Cyclopentenes Containing a Quaternary Chiral Center via a Thiosquaramide-Catalyzed Cascade Michael-Henry Reaction, HPLC of Formula: 5153-73-1, the publication is Journal of Organic Chemistry (2019), 84(23), 15655-15661, database is CAplus and MEDLINE.

An efficient method for the highly diastereoselective synthesis of chiral quaternary center-containing cyclopentenes via a cinchona alkaloid-derived thiosquaramide VIII-catalyzed tandem Michael-Henry reaction of phenacylmalononitriles and nitroolefins was developed. Meanwhile, up to 98% of enantioselectivity was observed A mechanism involving thiosquaramide-catalyzed asym. Michael addition and assisted E2 elimination was proposed based on exptl. data and preliminary theor. anal. (Hartree-Fock calculations).

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