Tag: M.W=150-200

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

Chen, Wen-Xin published the artcileBase-promoted N-alkylation using formamides as the N-sources in neat water, Computed Properties of 612-13-5, the publication is Tetrahedron (2014), 70(4), 880-885, database is CAplus.

An efficient catalyst-free, alternative method for the C-N bond formation reaction of alkyl electrophiles using formamides as the N-sources was achieved under mild conditions. The reaction possesses the advantages of a broad range of substrates scope and wide functional group tolerance. It should also be noted that this process was performed using the environmentally benign water as the sole solvent, and high yield can also be achieved in ten-gram scale.

Tetrahedron published new progress about 612-13-5. 612-13-5 belongs to nitriles-buliding-blocks, auxiliary class Organic Pigment, name is 2-(Chloromethyl)benzonitrile, and the molecular formula is C8H6ClN, Computed Properties of 612-13-5.

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

Lei, Zhen-lin published the artcileSynthesis with solvent-free and antifungal activities of 6-ether coumarin derivatives, Application In Synthesis of 612-13-5, the publication is Nongyao (2015), 54(10), 724-726, 743, database is CAplus.

2-Methyl-4-benzenediol was reacted with Et acetoacetate via Pechmann condensation to yield 6-hydroxy-4,7-dimethyl-coumarin, then the coumarin grinded with substituted benzyl chloride without solvent to yield twelve title compounds 4a-4l. The structure of the compounds were confirmed by ¹H NMR and LC-MS. The preliminary bioassay indicated some compounds, such as 4b, 4c and 4e, displayed over 90% antifungal activities against Botryodiplodia theobromae at 100 mg/L.

Nongyao published new progress about 612-13-5. 612-13-5 belongs to nitriles-buliding-blocks, auxiliary class Organic Pigment, name is 2-(Chloromethyl)benzonitrile, and the molecular formula is C8H6ClN, Application In Synthesis of 612-13-5.

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

Wang, Ming-Zhong published the artcileDesign, synthesis and antifungal activities of novel pyrrole alkaloid analogs, Application of 2-(Chloromethyl)benzonitrile, the publication is European Journal of Medicinal Chemistry (2011), 46(5), 1463-1472, database is CAplus and MEDLINE.

A series of novel analogs of pyrrole alkaloids were designed and synthesized by a facile method and their structures were characterized by ¹H NMR, ¹³C NMR and high-resolution mass spectrometry (HRMS). The structure of compound I was identified by 2D NMR including heteronuclear multiple-quantum coherence (HMQC), heteronuclear multiple-bond correlation (HMBC) and H-H correlation spectrometry (H-H COSY) spectra. Their antifungal activities against five fungi were evaluated, and the results indicated that some of the title compounds showed moderate fungicidal activities in vitro against Alternaria solani, Cercospora arachidicola, Fusarium omysporum, Gibberella zeae and Physalospora piricola at the dosage of 50 μg mL^-1. Compound I and its dibromo derivative exhibited good activities against P. piricola at low dosage.

European Journal of Medicinal Chemistry published new progress about 612-13-5. 612-13-5 belongs to nitriles-buliding-blocks, auxiliary class Organic Pigment, name is 2-(Chloromethyl)benzonitrile, and the molecular formula is C23H28N2O4, Application of 2-(Chloromethyl)benzonitrile.

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

He, Yu-Cai published the artcileBioproduction of glycolic acid from glycolonitrile with a new bacterial isolate of Alcaligenes sp. ECU0401, Safety of 2-(2-Chlorophenyl)-2-hydroxyacetonitrile, the publication is Applied Biochemistry and Biotechnology (2010), 160(5), 1428-1440, database is CAplus and MEDLINE.

Alcaligenes sp. ECU0401 has been isolated from soil samples with high nitrilase activity against glycolonitrile using the enrichment culture technique. The preferred carbon/nitrogen sources and metal ions were sodium acetate, a composite of peptone and yeast extract, and Cu²⁺, resp. Glycolic acid was obtained in a yield of 96.5% after 14 h of biotransformation from a total of 200 mM glycolonitrile in the mode of sequential addition during the cultivation of Alcaligenes sp. ECU0401 in a 5-L jar fermenter. Fifty micromolars of glycolonitrile could be hydrolyzed in a yield of 94.1% by resting cells after 36 h. The microbial nitrilase system could hydrolyze various nitriles with high activity, and no amidase activity and glycolic acid were observed in hydrolyzing glycolamide. It significantly exhibited high enantioselectivity in the hydrolysis of mandelonitrile and 2-chloromandelonitrile (>99.9% e.e._p). Efficient biocatalyst recycling was achieved as a result of immobilization in glutaraldehyde/polyethylenimine cross-linked carrageenan with immobilized cells exhibiting a biocatalyst productivity of 1,042.2 g glycolic acid per g dry cell weight after 29 batch recycles.

Applied Biochemistry and Biotechnology published new progress about 13312-84-0. 13312-84-0 belongs to nitriles-buliding-blocks, auxiliary class Chloride,Nitrile,Benzene,Alcohol,Benzene Compounds, name is 2-(2-Chlorophenyl)-2-hydroxyacetonitrile, and the molecular formula is C8H6ClNO, Safety of 2-(2-Chlorophenyl)-2-hydroxyacetonitrile.

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

Lan, Feng published the artcileSyntheses and herbicidal activities of novel 1,2,4-triazolinone derivatives, Formula: C8H6ClN, the publication is Gaodeng Xuexiao Huaxue Xuebao (2009), 30(4), 712-715, database is CAplus.

Environmentally benign triazolinone herbicides have a broad application perspective. Several triazolinone compounds such as amicarbazone, sulfentrazone [i.e., N-[2,4-dichloro-5-[4-(difluoromethyl)-4,5-dihydro-3-methyl-5-oxo-1H-1,2,4-triazol-1-yl]phenyl]methanesulfonamide], azafenidin [i.e., 2-[2,4-dichloro-5-(2-propyn-1-yloxy)phenyl]-5,6,7,8-tetrahydro-1,2,4-triazolo[4,3-a]pyridin-3(2H)-one] and carfentrazone-Et [i.e., α,2-dichloro-5-[4-(difluoromethyl)-4,5-dihydro-3-methyl-5-oxo-1H-1,2,4-triazol-1-yl]-4-fluorobenzenepropanoic acid Et ester] have already been developed as herbicides. In order to search for novel 1,2,4-triazolinone derivatives with high herbicidal activity, 2-(2,4,5-trichlorophenyl)-4-(benzyl)-5-methyl-3H-1,2,4-triazol-3-one derivatives and 2,4-bis(benzyl)-1,2,4-triazol-3-one derivatives were designed and synthesized. Their structures were determined by NMR, MS, elemental anal. The results of preliminary biol. activity tests show that some compounds display excellent herbicidal activity and some display good activity toward promoting cucumber cotyledon root-formation at 1.5 kg/ha.

Gaodeng Xuexiao Huaxue Xuebao published new progress about 612-13-5. 612-13-5 belongs to nitriles-buliding-blocks, auxiliary class Organic Pigment, name is 2-(Chloromethyl)benzonitrile, and the molecular formula is C8H6ClN, Formula: C8H6ClN.

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

Chu, Xue-Qiang published the artcileTBAI-Catalyzed/Water-Assisted Double C-S Bond Formations: An Efficient Approach to Sulfides through Metal-Free Three-Component Reactions, Recommanded Product: 2-(Chloromethyl)benzonitrile, the publication is Chemistry – A European Journal (2016), 22(40), 14181-14185, database is CAplus and MEDLINE.

An aqueous catalytic method for double C-S bond formations that involves alc. derivatives, organic halides, and sodium thiosulfate was developed. A diverse range of functionalized sulfides, including pharmaceutical and biol. derivatives, can be obtained in an efficient and eco-friendly manner under air. The mechanistic studies revealed that this tetrabutylammonium-iodide-catalyzed/water-assisted reaction generated a mercaptan species as the key intermediate.

Chemistry – A European Journal published new progress about 612-13-5. 612-13-5 belongs to nitriles-buliding-blocks, auxiliary class Organic Pigment, name is 2-(Chloromethyl)benzonitrile, and the molecular formula is C8H6ClN, Recommanded Product: 2-(Chloromethyl)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