Tag: M.W=150-200

Liu, Huijun published the artcileHighly chemoselective and efficient Strecker reaction of aldehydes with TMSCN catalyzed by MgI₂ etherate under solvent-free conditions, Recommanded Product: 2-(2-Chlorophenyl)-2-hydroxyacetonitrile, the publication is Phosphorus, Sulfur and Silicon and the Related Elements (2019), 194(9), 933-936, database is CAplus.

Strecker reaction of various substituted aromatic aldehydes, heteroaromatic aldehydes, aliphatic aldehydes and α,β-unsaturated aldehydes with trimethylsilyl cyanide (TMSCN) was realized in the presence of 5 mol % of MgI₂ etherate in a mild, efficient and highly chemoselective manner under solvent-free conditions.

Phosphorus, Sulfur and Silicon and the Related Elements 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, Recommanded Product: 2-(2-Chlorophenyl)-2-hydroxyacetonitrile.

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

Anand, Devireddy published the artcileA photocatalytic sp³ C-S, C-Se and C-B bond formation through C-C bond cleavage of cycloketone oxime esters, HPLC of Formula: 238088-16-9, the publication is Organic & Biomolecular Chemistry (2019), 17(3), 533-540, database is CAplus and MEDLINE.

The photocatalytic thiolation, selenylation and borylation of cycloketone oxime esters through iminyl radical-triggered C-C bond cleavage were described. The reactions provide a unified approach to alkyl sulfur, selenium and boron compounds tethered to a synthetically useful nitrile group.

Organic & Biomolecular Chemistry 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 C10H18BNO2, HPLC of Formula: 238088-16-9.

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

Man, Hon-Wah published the artcileA Highly Enantioselective and Diastereoselective Synthesis of Cyclobutanes via Boronic Esters, COA of Formula: C10H18BNO2, the publication is Organic Letters (1999), 1(3), 379-381, database is CAplus and MEDLINE.

Deprotonation of enantiopure (R,R)-1,2-dicyclohexyl-1,2-ethanediol 1-chloro-4-cyanobutylboronates with LDA followed by treatment with anhydrous magnesium bromide yields (R)-(trans-2-cyanocyclobutyl)boronic esters 7 in high diastereomeric and enantiomeric purity. No cyclobutane formation has been observed in the absence of at least a catalytic amount of magnesium halide.

Organic Letters 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 C10H18BNO2, COA of Formula: C10H18BNO2.

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

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

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

Sun, Huihui published the artcileCloning, purification and evaluation of the enzymatic properties of a novel arylacetonitrilase from Luminiphilus syltensis NOR5-1B: a potential biocatalyst for the synthesis of mandelic acid and its derivatives, Category: nitriles-buliding-blocks, the publication is Biotechnology Letters (2015), 37(8), 1655-1661, database is CAplus and MEDLINE.

Objective: To examine nitrilase-mediated hydrolysis of nitriles to produce optically pure α-hydroxycarboxylic acids. Results: A novel nitrilase, GPnor51, from Luminiphilus syltensis NOR5-1B was discovered by genomic data mining. It could hydrolyze racemic o-chloromandelonitrile to (R)-o-chloromandelic acid with high enantioselectivity (ee 98.2 %). GPnor51 was overexpressed in Escherichia coli BL21 (DE3), purified, and its catalytic properties studied. GPnor51 had a broad substrate acceptance toward various nitriles with structure diversity. It was an arylacetonitrilase that uses arylacetonitriles as optimal substrates. The V_max and K_m of GPnor51 towards o-chloromandelonitrile were 1.9 μmol min^-1 mg^-1 protein and 0.38 mM, resp. GPnor51 also demonstrated high enantioselectivity toward mandelonitrile and other substituted mandelonitrile. Conclusion: This enzyme has a great potential for com. production of optically pure (R)-mandelic acid and its derivatives

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 C10H13NO2, Category: nitriles-buliding-blocks.

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

Wang, Hualei published the artcileProtein engineering of a nitrilase from Burkholderia cenocepacia J2315 for efficient and enantioselective production of (R)-o-chloromandelic acid, Related Products of nitriles-buliding-blocks, the publication is Applied and Environmental Microbiology (2015), 81(24), 8469-8477, database is CAplus and MEDLINE.

The nitrilase-mediated pathway has significant advantages in the production of optically pure aromatic α-hydroxy carboxylic acids. However, low enantioselectivity and activity are observed on hydrolyzing o-chloromandelonitrile to produce optically pure (R)-o-chloromandelic acid. A protein engineering approach was successfully used to enhance the performance of nitrilase obtained from Burkholderia cenocepacia strain J2315 (BCJ2315) in hydrolyzing o-chloromandelonitrile. Four hot spots (T49, I113, Y199, and T310) responsible for the enantioselectivity and activity of BCJ2315 were identified by random mutagenesis. An effective double mutant (I113M/Y199G [encoding the replacement of I with M at position 113 and Y with G at position 199]), which demonstrated remarkably enhanced enantioselectivity (99.1% enantiomeric excess [ee] compared to 89.2% ee for the wild type) and relative activity (360% of the wild type), was created by two rounds of site saturation mutagenesis, first at each of the four hot spots and subsequently at position 199 for combination with the selected beneficial mutation I113M. Notably, this mutant also demonstrated dramatically enhanced enantioselectivity and activity toward other mandelonitrile derivatives and, thus, broadened the substrate scope of this nitrilase. Using an Et acetate-water (1:9) biphasic system, o-chloromandelonitrile (500 mM) was completely hydrolyzed in 3 h by this mutant with a small amount of biocatalyst (10 g/L wet cells), resulting in a high concentration of (R)-o-chloromandelic acid with 98.7% ee, to the authors’ knowledge the highest ever reported. This result highlights a promising method for industrial production of optically pure (R)-o-chloromandelic acid. Insight into the source of enantioselectivity and activity was gained by homol. modeling and mol. docking experiments

Applied and Environmental Microbiology 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 C18H10, Related Products of nitriles-buliding-blocks.

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

McEwen, William E. published the artcileSynthetic uses of open-chain analogs of Reissert compounds, Related Products of nitriles-buliding-blocks, the publication is Journal of Organic Chemistry (1980), 45(7), 1301-8, database is CAplus.

Open-chain analogs, RN(COR²)CHR¹CN (I, R = Ph, PhCH₂, p-ClC₆H₄, p-MeOC₆H₄, Me(CH₂)₅, cyclohexyl; R¹ = Ph, H, o-, m-, p-ClC₆H₄, 3,4-(MeO)₂C₆H₃, o-, m-MeOC₆H₄, Bu; R² = Ph, Me), of Reissert compounds are obtained by reaction of R¹CH(OH)CN with RNH₂, the resulting aminonitriles, RNHCHR¹CN, then being acylated. Hydrofluoroborate salts, II, of I, are prepared by reaction with fluoroboric acid in HOAc. The salts, II, undergo 1,3-dipolar addition reactions with reactive alkynes to give substituted pyrroles and with Et acrylate to give a different type of substituted pyrrole, the initial step in this instance being a Diels-Alder reaction. Thus, addition of MeO₂CCCCO₂Me to II (R¹ = R² = Ph) gave III (R = Ph, m-ClC₆H₄, p-MeOC₆H₄, PhCH₂); and addition of H₂C:CHCO₂Et to II (R = R¹ = R² = Ph) gave IV. I also undergo base-catalyzed reactions, such as alkylation with R⁵Br to provide R²CONRCR¹R⁵CN (R⁵ = PhCH₂, Bu, α-naphthylmethyl, R-R² = as above), which, in turn, undergo cleavage reactions in ethanolic alkali to give ketones R¹R⁵CO. A conjugate addition reaction of the anion BzNPhC^–PhCN (V) to Me acrylate to give, after subsequent steps, VI was demonstrated. α-Anilino ketones, PhNHCHRCOR¹, result when the anion V is treated with aldehydes, the initial reaction mixtures being subjected to subsequent alk. hydrolysis. Finally, N-benzyl Reissert analogs give desoxybenzoins plus benzonitriles on treatment with NaH in THF.

Journal of Organic Chemistry 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, Related Products of nitriles-buliding-blocks.

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