Month: December 2022

Sun, Huihui published the artcileExpression, characterization of a novel nitrilase PpL19 from Pseudomonas psychrotolerans with S-selectivity toward mandelonitrile present in active inclusion bodies, Name: 2-(2-Chlorophenyl)-2-hydroxyacetonitrile, the publication is Biotechnology Letters (2016), 38(3), 455-461, database is CAplus and MEDLINE.

Objectives: To identify a novel nitrilase with S-selectivity toward mandelonitrile that can produce (S)-mandelic acid in one step. Results: A novel nitrilase PpL19 from Pseudomonas psychrotolerans L19 was discovered by genome mining. It showed S-selectivity with an enantiomeric excess of 52.7% when used to hydrolyze (R,S)-mandelonitrile. No byproduct was observed PpL19 was overexpressed in Escherichia coli BL21 (DE3) and formed inclusion bodies that were active toward mandelonitrile and stable across a broad range of temperature and pH. In addition, PpL19 hydrolyzed nitriles with diverse structures; arylacetonitriles were the optimal substrates. Homol. modeling and docking studies of both enantiomers of mandelonitrile in the active site of nitrilase PpL19 shed light on the enantioselectivity. Conclusions: A novel nitrilase PpL19 from P. psychrotolerans L19 was mined and distinguished from other nitrilases as it was expressed as an active inclusion body and showed S-selectivity toward mandelonitrile.

Biotechnology Letters 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 C10H9NO, Name: 2-(2-Chlorophenyl)-2-hydroxyacetonitrile.

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

Wan, Jinlin published the artcileDesign, synthesis and anti-bacterial evaluation of novel 1,3,4-thiadiazole derivatives bearing a semicarbazone moiety, Application In Synthesis of 612-13-5, the publication is Phosphorus, Sulfur and Silicon and the Related Elements (2018), 193(7), 443-450, database is CAplus.

(Alkylthio)thiadiazolyl semicarbazones of 2-chloro-3-indolecarboxaldehyde I (R = R¹CH₂, Me, Et, n-Pr, Bu, BuCH₂; R¹ = Ph, 2-ClC₆H₄, 3-ClC₆H₄, 4-ClC₆H₄, 2-MeOC₆H₄, 3-MeOC₆H₄, 4-MeOC₆H₄, 2-MeC₆H₄, 3-MeC₆H₄, 4-MeC₆H₄, 2-FC₆H₄, 4-FC₆H₄, 2-NCC₆H₄, 2,4-Cl₂C₆H₃) were prepared as agrochem. antibacterial agents for treatment of rice bacterial leaf blight (Xanthomonas oryzae pv. oryzae, Xoo) and citrus canker (Xanthomonas axonopodis pv. citri, Xac). I were prepared in four steps from 5-amino-1,3,4-thiadiazole-2-thiol, benzyl chlorides or alkyl bromides, and 2-chloro-3-indolecarboxaldehyde (prepared in one step from oxindole). Many of the tested compounds exhibited excellent activity (≥74.19%) against Xoo at a concentration of 200 μg/mL, with 50% effective concentration (EC₅₀) values ranging from 12.21 to 67.20 μg/mL, superior to the com. antibacterial agent bismerthiazol (EC₅₀ = 92.23 μg/mL). I (R = 2-ClC₆H₄CH₂) demonstrated good inhibitory activity against Xac (89.46% at 200 μg/mL) and Xoo (EC₅₀ = 18.28 μg/mL), while I (R = 4-MeOC₆H₄CH₂) displayed excellent activity against Xoo with an EC₅₀ value of 12.21 μg/mL.

Phosphorus, Sulfur and Silicon and the Related Elements 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 C15H14Cl2S2, Application In Synthesis of 612-13-5.

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

Sau, Abhijit published the artcilePalladium-Catalyzed α-Stereoselective O-Glycosylation of O(3)-Acylated Glycals, Formula: C10H12F6N4O6PdS2, the publication is Organic Letters (2017), 19(11), 2857-2860, database is CAplus and MEDLINE.

Pd(MeCN)₂Cl₂ enables the α-stereoselective catalytic synthesis of 2,3-unsaturated O-glycosides from O(3)-acylated glycals without the requirement for additives to pre-activate either donor or nucleophile. Mechanistic studies suggest that, unlike traditional (η3-allyl)palladium-mediated processes, the reaction proceeds via an alkoxy-palladium intermediate that increases the proton acidity and oxygen nucleophilicity of the alc. The method is exemplified with the synthesis of a range of glycosides and glycoconjugates of synthetic utility.

Organic Letters published new progress about 68569-14-2. 68569-14-2 belongs to nitriles-buliding-blocks, auxiliary class Palladium, name is Tetrakis(acetonitrile)palladium(II) Ditriflate, and the molecular formula is C10H12F6N4O6PdS2, Formula: C10H12F6N4O6PdS2.

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

Sakata, Yoko published the artcileFunctionalized metallonanobelt derivatives having quinoxaline scaffold prepared from a common precursor, Name: Tetrakis(acetonitrile)palladium(II) Ditriflate, the publication is Tetrahedron Letters (2019), 60(31), 2049-2053, database is CAplus.

Synthesis of functionalized pentamer metallonanobelts was accomplished by using a series of triptycene ligands, which were synthesized by quinoxaline formation from 2,3,6,7,14,15-hexaaminotriptycene as a common precursor. It was also found that two kinds of template-bound metal complexes were selectively formed by changing the ratio of Pd²⁺/ligand.

Tetrahedron Letters published new progress about 68569-14-2. 68569-14-2 belongs to nitriles-buliding-blocks, auxiliary class Palladium, name is Tetrakis(acetonitrile)palladium(II) Ditriflate, and the molecular formula is C10H12F6N4O6PdS2, Name: Tetrakis(acetonitrile)palladium(II) Ditriflate.

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

Yamamoto, Yasunori published the artcileIridium-catalyzed hydroboration of alkenes with pinacolborane, Synthetic Route of 238088-16-9, the publication is Tetrahedron (2004), 60(47), 10695-10700, database is CAplus.

Hydroboration of terminal and internal alkenes with pinacolborane was carried out at room temperature in the presence of an iridium(I) catalyst. Addition of dppm to [Ir(cod)Cl]₂ gave the best catalyst for hydroboration of aliphatic terminal and internal alkenes at room temperature, resulting in addition of the boron atom to the terminal carbon of 1-alkenes with excellent selectivities. On the other hand, a complex prepared from dppe and [Ir(cod)Cl]₂ resulted in the best yields for vinylarenes such as styrene. These complexes exhibited higher levels of catalyst activity and selectivity than those of corresponding rhodium complexes.

Tetrahedron published new progress about 238088-16-9. 238088-16-9 belongs to nitriles-buliding-blocks, auxiliary class Nitrile,Boronic acid and ester,Aliphatic cyclic hydrocarbon,Boronic Acids,Boronate Esters, name is 4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)butanenitrile, and the molecular formula is C44H28ClFeN4, Synthetic Route of 238088-16-9.

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

Chan, Kelvin S. L. published the artcilePalladium(II)-Catalyzed Highly Enantioselective C-H Arylation of Cyclopropylmethylamines, Recommanded Product: Tetrakis(acetonitrile)palladium(II) Ditriflate, the publication is Journal of the American Chemical Society (2015), 137(5), 2042-2046, database is CAplus and MEDLINE.

C-H arylation via a Pd(II)/Pd(IV) catalytic cycle has been one of the most extensively studied C-H activation reactions since the 1990s. Despite the rapid development of this reaction in the past two decades, an enantioselective version has not been reported to date. Herein, we report a Pd(II)-catalyzed highly enantioselective (up to 99.5% ee) arylation of cyclopropyl C-H bonds with aryl iodides using mono-N-protected amino acid (MPAA) ligands, providing a new route for the preparation of chiral cis-aryl-cyclopropylmethylamines, e.g., I [R¹ = H, Me, CH₂Ph, Ph, C₆H₃F₂-2,6, CH₂OSiMe₂CMe₃, CO₂Me]. The enantiocontrol is also shown to override the diastereoselectivity of chiral substrates.

Journal of the American Chemical Society published new progress about 68569-14-2. 68569-14-2 belongs to nitriles-buliding-blocks, auxiliary class Palladium, name is Tetrakis(acetonitrile)palladium(II) Ditriflate, and the molecular formula is C10H12F6N4O6PdS2, Recommanded Product: Tetrakis(acetonitrile)palladium(II) Ditriflate.

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

Andersson, Carlaxel published the artcileThe influence of metal coordination on ligand geometry: the structures of 2-(diphenylphosphino)benzyl methyl ether and bis(2-(diphenylphosphino)benzyl methyl ether)palladium(II)triflate, Recommanded Product: Tetrakis(acetonitrile)palladium(II) Ditriflate, the publication is Journal of Molecular Structure (1999), 479(1), 1-11, database is CAplus.

The structures of 2-(diphenylphosphino)benzyl Me ether (I) and bis(2-(diphenylphosphino)benzyl Me ether)palladium(II)triflate (II) were determined by x-ray crystallog. II is a potential catalyst in organic synthesis and was prepared by treating tetrakis(acetonitrile)palladium bistriflate with 2-(diphenylphosphino)benzyl Me ether in toluene for 16 h at room temperature I crystallizes in monoclinic space group P2₁/a with a 7.873(2), b 14.805(3), c 14.262(5) Å, β 91.34(3)°, and Z = 4. II crystallizes in triclinic space group P1̅ with a 10.2886(6), b 13.951(1), c 15.6339(9) Å, α 89.171(5), β 73.791(5), γ 83.463(6)°, and Z = 2. Both structures were solved by direct methods and the refinements resulted in the R-values 0.066 and 0.052 for I and II, resp. The bidentate ligand binds to Pd(II) in a cis-configuration. The Pd-O distances are 2.153(3) and 2.142(3) A and the Pd-P distances 2.252(1) and 2.256(1) Å. The effects of packing and metal complexation on the geometry of I are discussed and the differences are compared by half-normal probability plot anal.

Journal of Molecular Structure published new progress about 68569-14-2. 68569-14-2 belongs to nitriles-buliding-blocks, auxiliary class Palladium, name is Tetrakis(acetonitrile)palladium(II) Ditriflate, and the molecular formula is C10H12F6N4O6PdS2, Recommanded Product: Tetrakis(acetonitrile)palladium(II) Ditriflate.

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

Visser, Michael S. published the artcileSynthesis and biological evaluation of novel hygromycin A antibacterial agents, Name: 2-(Chloromethyl)benzonitrile, the publication is Bioorganic & Medicinal Chemistry Letters (2010), 20(22), 6730-6734, database is CAplus and MEDLINE.

Novel hygromycin A derivatives, e.g. I, bearing a variety of functionalized aminocyclitol moieties have been synthesized in an effort to increase the antibacterial activity and drug-like properties of this class of agents. A systematic study of the effect of alkylation and removal of the hydroxyls of the aminocyclitol directed us to a series of alkylated aminocyclitol derivatives with improved Gram-pos. activity.

Bioorganic & Medicinal Chemistry Letters 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 C5H6BNO2, Name: 2-(Chloromethyl)benzonitrile.

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

Gutierrez-Bonet, Alvaro published the artcileFe-Catalyzed Regiodivergent [1,2]-Shift of α-Aryl Aldehydes, Category: nitriles-buliding-blocks, the publication is Journal of the American Chemical Society (2013), 135(34), 12576-12579, database is CAplus and MEDLINE.

An Fe-catalyzed conversion of aldehydes to ketones via [1,2]-shift has been developed. This skeletal rearrangement shows a wide substrate scope and chemoselectivity profile while exhibiting an excellent [1,2]-aryl or [1,2]-alkyl shift selectivity that is easily switched by electronic effects.

Journal of the American Chemical Society 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, Category: nitriles-buliding-blocks.

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