Category: nitriles-buliding-blocks

Yang, Chu-Ting published the artcileCopper-Catalyzed Cross-Coupling Reaction of Organoboron Compounds with Primary Alkyl Halides and Pseudohalides, Category: nitriles-buliding-blocks, the publication is Angewandte Chemie, International Edition (2011), 50(17), 3904-3907, S3904/1-S3904/108, database is CAplus and MEDLINE.

A copper-catalyzed cross-coupling of non-activated alkyl electrophiles with organoboron compounds has been developed. The use of LiOtBu as a base was found to be crucial to the reaction. The reaction is applicable to alkyl iodides, bromides, tosylates, mesylates, and even chlorides, and tolerates many more functional groups than the previously described copper-catalyzed coupling of Grignard reagents. It provides practically useful reactivities and may thus compliment palladium and nickel-catalyzed Suzuki-Miyaura coupling reactions of alkyl halides.

Angewandte Chemie, International Edition published new progress about 214360-44-8. 214360-44-8 belongs to nitriles-buliding-blocks, auxiliary class Nitrile,Boronic acid and ester,Benzene,Boronic Acids,Boronic acid and ester, name is 4-(5,5-Dimethyl-1,3,2-dioxaborinan-2-yl)benzonitrile, and the molecular formula is C4H7F3O2, Category: nitriles-buliding-blocks.

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

He, Yu-Cai published the artcileBiocatalytic synthesis of (R)-(-)-mandelic acid from racemic mandelonitrile by cetyltrimethylammonium bromide-permeabilized cells of Alcaligenes faecalis ECU0401, Synthetic Route of 13312-84-0, the publication is Journal of Industrial Microbiology & Biotechnology (2010), 37(7), 741-750, database is CAplus and MEDLINE.

The nitrilase from Alcaligenes faecalis ECU0401 belongs to the category of arylacetonitrilase, which could hydrolyze 2-chloromandelonitrile, 3,4-dimethoxyphenylacetonitrile, mandelonitrile, and phenylacetonitrile into the corresponding arylacetic acids. To overcome the permeability barrier and prepare whole cell biocatalysts with high activities, permeabilization of Alcaligenes faecalis ECU0401 in relation to nitrilase activity was optimized by using cetyltrimethylammonium bromide (CTAB) as permeabilizing agent. The nitrilase activity from Alcaligenes faecalis ECU0401 increased 4.5-fold when the cells were permeabilized with 0.3% (w/v) CTAB for 20 min at 25°C and pH 6.5. Consequently, almost all the mandelonitrile was consumed and converted to (R)-(-)-mandelic acid with greater than 99.9% enantiomeric excess (e.e.) by the CTAB-permeabilized cells. The permeability barrier has been significantly reduced in the hydrolysis of mandelonitrile by using CTAB-permeabilized cells and a dynamic resolution was successfully achieved, giving a 100% theor. yield of (R)-(-)-mandelic acid. Efficient biocatalyst recycling was achieved as a result of cell immobilization in calcium alginate, with a product-to-biocatalyst ratio of 3.82 g (R)-(-)-mandelic acid g^-1 dry cell weight (dcw) cell after 20 cycles of repeated use.

Journal of Industrial Microbiology & 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, Synthetic Route of 13312-84-0.

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

Zhang, Chen-Sheng published the artcileEfficient production of (R)-o-chloromandelic acid by deracemization of o-chloromandelonitrile with a new nitrilase mined from Labrenzia aggregata, Category: nitriles-buliding-blocks, the publication is Applied Microbiology and Biotechnology (2012), 95(1), 91-99, database is CAplus and MEDLINE.

(R)-o-Chloromandelic acid (I) is the key precursor for the synthesis of Clopidogrel, a best-selling cardiovascular drug. Although nitrilases are often used as an efficient tool in the production of α-hydroxy acids, there is no practical nitrilase specifically developed for I. Here, a new nitrilase from L. aggregata (II) was discovered for the 1st time by genomic data mining, which hydrolyzed o-chloromandelonitrile (III) with high enantioselectivity, yielding (R)-o-chloromandelic acid in 96.5% ee. II was overexpressed in Escherichia coli BL21 (DE3), purified, and its catalytic properties were studied. When III was used as the substrate, the V_max and K_m values of II were 2.53 μmol min^-1 mg^-1 protein and 0.39 mM, resp., indicating its high catalytic efficiency. In addition, a study of the substrate spectrum showed that II preferred to hydrolyze arylacetonitriles. To relieve substrate inhibition and to improve the productivity of II, a biphasic system of toluene-water (1:9, volume/volume) was adopted, in which III at 300 mM (apparent concentration, based on total volume) could be transformed by II in 8 h, giving an isolated yield of 94.5%. Thus, the development of II makes it possible to produce I by deracemizing III with a good ee value and high substrate concentration

Applied Microbiology 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 C2H4ClNO, Category: nitriles-buliding-blocks.

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

Xu, Jian-Xing published the artcileRuthenium-Catalyzed Carbonylative Coupling of Anilines with Organoboranes by the Cleavage of Neutral Aryl C-N Bond, Quality Control of 214360-44-8, the publication is Organic Letters (2020), 22(7), 2756-2760, database is CAplus and MEDLINE.

Herein, the first ruthenium-catalyzed Suzuki-type carbonylative reaction of electronically neutral anilines I (R¹ = H; R² = Me, F, Cl, t-Bu, H; R³ = H, F; R¹R² = -CH=CH-CH=CH-) and N,N-dimethyl-2-(pyrimidin-2-yl)aniline via C(aryl)-N bond cleavage was reported. Without any ligand and base, diaryl ketones II (R⁴ = 3-bromophenyl, 2,4,6-trimethylphenyl, 2-naphthyl, etc.) and phenyl(2-(pyrimidin-2-yl)phenyl)methanone can be obtained in moderate to high yields by using Ru₃(CO)₁₂ as the catalyst and chelation assisted by pyridine. The pyridine ring has a significant effect on both high efficiency and high regioselectivity in the cleavage of the aryl C-N bond in anilines.

Organic Letters published new progress about 214360-44-8. 214360-44-8 belongs to nitriles-buliding-blocks, auxiliary class Nitrile,Boronic acid and ester,Benzene,Boronic Acids,Boronic acid and ester, name is 4-(5,5-Dimethyl-1,3,2-dioxaborinan-2-yl)benzonitrile, and the molecular formula is C14H23N, Quality Control of 214360-44-8.

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

Wang, Guan published the artcileDiscovery of a Novel Dual-Target Inhibitor of ERK1 and ERK5 That Induces Regulated Cell Death to Overcome Compensatory Mechanism in Specific Tumor Types, Recommanded Product: 2-(Chloromethyl)benzonitrile, the publication is Journal of Medicinal Chemistry (2020), 63(8), 3976-3995, database is CAplus and MEDLINE.

ERK1 and ERK5 are proposed to have pivotal roles in several types of cancer. Under some circumstance, ERK5 may provide a common bypass route, which rescues proliferation upon abrogation of ERK1 signaling. Thus, we accurately classified the tumor types from The Cancer Genome Atlas (TCGA) based on the expression levels of ERK1 and ERK5. We proposed a novel therapeutic strategy to overcome the above-mentioned compensatory mechanism in specific tumor types by co-targeting both ERK1 and ERK5. On the basis of the idea of overcoming ERK5 compensation mechanism, 22ac (ADTL-EI1712) as the first selective dual-target inhibitor of ERK1 and ERK5 was discovered to have potent antitumor effects in vitro and in vivo. Interestingly, this compound was found to induce regulated cell death accompanied by autophagy in MKN-74 cells. Taken together, our results warrant the potential of this dual-target inhibitor as a new candidate drug that conquers compensatory mechanism in certain tumor types.

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 C6H12O2, Recommanded Product: 2-(Chloromethyl)benzonitrile.

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

Qiao, Jin-Bao published the artcileAllylboronates from Vinyl Triflates and α-Chloroboronates by Reductive Nickel Catalysis, Recommanded Product: 4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)butanenitrile, the publication is Organic Letters (2020), 22(13), 5085-5089, database is CAplus and MEDLINE.

Allylboronates are unique building blocks widely used in organic synthesis, but the construction of cyclic allylboranates remains a challenging subject. The authors demonstrate here a mild and efficient access to this type of compound through the cross-electrophile coupling of vinyl triflates and α-chloroboronates. The reaction proceeded with a good substrate scope and good functional group compatibility. The ready availability of vinyl triflates from ketones, as well as the rich chem. of allylboranates, makes the authors’ method suitable for the divergent modification of biol. active compounds Preliminary mechanistic studies revealed that α-chloroboronates were activated via a radical process.

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, Recommanded Product: 4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)butanenitrile.

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

Zhang, Chun-Bo published the artcileDesign and synthesis of 6-alkyloxy[1,2,4]triazolo[1,5-a]quinazoline derivatives with anticonvulsant activity, Synthetic Route of 612-13-5, the publication is Medicinal Chemistry Research (2012), 21(10), 3294-3300, database is CAplus.

6-(Benzyloxy or alkoxy)[1,2,4]triazolo[1,5-a]quinazoline derivatives were synthesized in four steps starting from 1,3-cyclohexanedione, DMF-DMA, and aminotriazole followed by bromination, dehydrobromination and finally reaction with benzyl or alkyl halides. The anticonvulsant activity of all the target compounds, characterized by IR, ¹H-NMR and MS, were evaluated using Maximal electroshock test. The pharmacol. results showed that some of the compounds displayed pos. anticonvulsant activity. Among them, 6-(benzyloxy)-[1,2,4]triazolo[1,5-a]quinazoline was the most active compound with an ED₅₀ value of 78.9 mg/kg and a PI value of 9.0.

Medicinal Chemistry Research 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 C22H18Cl2N2, Synthetic Route of 612-13-5.

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

Zhang, Mengmeng published the artcileVisible Light Mediated C(sp³)-H Alkenylation of Cyclic Ethers Enabled by Aryl Ketone, Formula: C9H6N2O2, the publication is ChemCatChem (2019), 11(6), 1606-1609, database is CAplus.

C-H Alkenylation of cyclic ethers (THF, 1,4-dioxane) using the readily available nitroalkenes as the alkenylating reagents which gave α-alkenyl ethers Ar(CH:CH)_nR [Ar = Ph, 2-naphthyl, 2-thienyl, etc.; R = 1,2-dimethoxyethane, tetrahydrofuran-2-yl, 1,4-dioxan-2-yl] with high E-selectivity was developed. The mechanism study revealed that alkenylation proceeded through a proton coupled electron transfer (PCET) process with a de-nitration.

ChemCatChem 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 C8H16O2, Formula: C9H6N2O2.

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

Chen, Peiran published the artcileKinetic resolution of mandelate esters via stereoselective acylation catalyzed by lipase PS-30, Safety of 2-(2-Chlorophenyl)-2-hydroxyacetonitrile, the publication is Tetrahedron Letters (2014), 55(14), 2290-2294, database is CAplus.

By using lipase PS-30 as catalyst, the kinetic resolution of a series of racemic mandelate esters has been achieved via stereoselective acylation. The value of kinetic enantiomeric ratio (E) reached up to 197.5. Substituent effect is briefly discussed.

Tetrahedron 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 C8H6ClNO, Safety of 2-(2-Chlorophenyl)-2-hydroxyacetonitrile.

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

Dou, Xiaowei published the artcileAsymmetric synthesis of 3-spirocyclopropyl-2-oxindoles via intramolecular trapping of chiral aza-ortho-xylylene, Category: nitriles-buliding-blocks, the publication is Chemical Communications (Cambridge, United Kingdom) (2013), 49(80), 9224-9226, database is CAplus and MEDLINE.

Chiral aza-ortho-xylylene intermediates were efficiently generated from 3-chloro-3-substituted oxindole precursors I (R = H, 5-Br, 6-Cl, 5-Cl) and (E)-R¹CH:CHNO₂ (R¹ = Ph, 2-BrC₆H₄, 3-BrC₆H₄, 3-ClC₆H₄, 4-ClC₆H₄, 4-FC₆H₄, 2-MeC₆H₄, 4-MeOC₆H₄, 4-NCC₆H₄, 1-naphthyl, 2-furyl, 2-thienyl, phenethyl). The process was catalyzed by chiral quinine derivative II. The first intramol. trapping of chiral aza-ortho-xylylene intermediates led to a highly asym. synthesis of 3-spirocyclopropyl-2-oxindoles III.

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, Category: nitriles-buliding-blocks.

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