Tag: M.W=150-200

Juhl, Martin published the artcileCO₂-Enabled Cyanohydrin Synthesis and Facile Iterative Homologation Reactions, Category: nitriles-buliding-blocks, the publication is Chemistry – A European Journal (2021), 27(1), 228-232, database is CAplus and MEDLINE.

Use of carbon dioxide/carbon disulfide to accelerate cyanohydrin RR¹COHCN [R = cyclohexyl, Ph, 2-furyl, etc.; R¹ = H, CO₂H] and R²CHOC(S)SMeCN [R² = 4-FC₆H₄, (CH₂)₂Ph] syntheses starting from alkyl- and aryl aldehydes under neutral conditions with an insoluble cyanide source (KCN) without generating toxic HCN were reported. Under inert atm., the reaction was essentially not operative due to the unfavored equilibrium The utility of CO₂-mediated selective cyanohydrin synthesis was further showcased by broadening Kiliani-Fischer synthesis under neutral conditions. This protocol offered an easy access to a variety of polyols, cyanohydrins, linear alkylnitriles, by simply starting from alkyl- and arylaldehydes, KCN and an atm. pressure of CO².

Chemistry – A European Journal 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

Dianati, Vahid published the artcileImproving the Selectivity of PACE4 Inhibitors through Modifications of the P1 Residue, Application In Synthesis of 5153-73-1, the publication is Journal of Medicinal Chemistry (2018), 61(24), 11250-11260, database is CAplus and MEDLINE.

Paired basic amino acid cleaving enzyme 4 (PACE4), a serine endoprotease of the proprotein convertases family, has been recognized as a promising target for prostate cancer. We previously reported a selective and potent peptide-based inhibitor for PACE4, named the multi-Leu peptide (Ac-LLLLRVKR-NH₂ sequence), which was then modified into a more potent and stable compound named C23 with the following structure: Ac-DLeu-LLLRVK-Amba (Amba: 4-amidinobenzylamide). Despite improvements in both in vitro and in vivo profiles of C23, its selectivity for PACE4 over furin was significantly reduced. We examined other Arg-mimetics instead of Amba to regain the lost selectivity. Our results indicated that the replacement of Amba with 5-(aminomethyl)picolinimidamide increased affinity for PACE4 and restored selectivity. Our results also provide a better insight on how structural differences between S1 pockets of PACE4 and furin could be employed in the rational design of selective inhibitors.

Journal of Medicinal 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, Application In Synthesis of 5153-73-1.

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

Maity, Soham published the artcileStereoselective Nitration of Olefins with ^tBuONO and TEMPO: Direct Access to Nitroolefins under Metal-free Conditions, Application of (E)-4-(2-Nitrovinyl)benzonitrile, the publication is Organic Letters (2013), 15(13), 3384-3387, database is CAplus and MEDLINE.

Nitroolefins are essential elements for both synthetic chem. and medicinal research. Despite significant improvements in nitration of olefin an efficient metal-free synthesis remains elusive so far. Herein, we disclose a new set of reagents to access nitroolefins in a single step under metal-free conditions. A wide range of olefins with diverse functionalities has been nitrated in synthetically useful yields. This transformation is operationally simple and exhibits excellent E-selectivity. Furthermore, site selective nitration in a complex setup makes this method advantageous.

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

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

Suzuki, Kensuke published the artcile(o-Phenylenediamino)borylstannanes: Efficient Reagents for Borylation of Various Alkyl Radical Precursors, SDS of cas: 238088-16-9, the publication is Chemistry – A European Journal (2021), 27(12), 3968-3973, database is CAplus and MEDLINE.

(o-Phenylenediamino)borylstannanes were newly synthesized to achieve radical boryl substitutions of a variety of alkyl radical precursors. Dehalogenative, deaminative, dechalcogenative, and decarboxylative borylations proceeded in the presence of a radical initiator to give the corresponding organic B compounds Radical clock experiments and computational studies provided insights into the mechanism of the homolytic substitution (S_H2) of the borylstannanes with alkyl radical intermediates. DFT calculation disclosed that the phenylenediamino structure lowered the LUMO level including the vacant p-orbital on the B atom to enhance the reactivity to alkyl radicals in S_H2. Also, C(sp³)-H borylation of THF was accomplished using the triplet state of xanthone.

Chemistry – A European Journal 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 C14H23N, SDS of cas: 238088-16-9.

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

Sang, Ruocheng published the artcileChiral Benzothiophene Synthesis via Enantiospecific Coupling of Benzothiophene S-Oxides with Boronic Esters, Quality Control of 238088-16-9, the publication is Angewandte Chemie, International Edition (2021), 60(48), 25313-25317, database is CAplus and MEDLINE.

Benzothiophenes are valuable heterocycles that are widely used in medicines, agrochems., and materials science. Herein, a general method for the synthesis of enantioenriched 2,3-disubstituted benzothiophenes via a transition-metal-free C2-alkylation of benzothiophenes with boronic esters is reported. The reactions utilize benzothiophene S-oxides in lithiation-borylations to generate intermediate arylboronate complexes, and subsequent Tf₂O-promoted S-O bond cleavage to trigger a Pummerer-type 1,2-metalate shift, which gives the coupled products with complete enantiospecificity. Primary, secondary and tertiary alkyl boronic esters and aryl boronic esters are successfully coupled with a range of C3-substituted benzothiophenes. Importantly, this transformation does not require the use of C3 directing groups, therefore it overcomes a major limitation of previously developed transition-metal-mediated C2 alkylations of benzothiophenes.

Angewandte Chemie, International Edition 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, Quality Control of 238088-16-9.

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

Shu, Chao published the artcileMetal-free photoinduced C(sp³)-H borylation of alkanes, Recommanded Product: 4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)butanenitrile, the publication is Nature (London, United Kingdom) (2020), 586(7831), 714-719, database is CAplus and MEDLINE.

Boronic acids and their derivatives are some of the most useful reagents in the chem. sciences, with applications spanning pharmaceuticals, agrochems. and functional materials. Catalytic C-H borylation is a powerful method for introducing these and other boron groups into organic mols. because it can be used to directly functionalize C-H bonds of feedstock chems. without the need for substrate pre-activation. These reactions have traditionally relied on precious-metal catalysts for C-H bond cleavage and, as a result, display high selectivity for borylation of aromatic C(sp²)-H bonds over aliphatic C(sp³)-H bonds. Here we report a mechanistically distinct, metal-free borylation using hydrogen atom transfer catalysis, in which homolytic cleavage of C(sp³)-H bonds produces alkyl radicals that are borylated by direct reaction with a diboron reagent. The reaction proceeds by violet-light photoinduced electron transfer between an N-alkoxyphthalimide-based oxidant and a chloride hydrogen atom transfer catalyst. Unusually, stronger Me C-H bonds are borylated preferentially over weaker secondary, tertiary and even benzylic C-H bonds. Mechanistic studies indicate that the high Me selectivity is a result of the formation of a chlorine radical-boron ‘ate’ complex that selectively cleaves sterically unhindered C-H bonds. By using a photoinduced hydrogen atom transfer strategy, this metal-free C(sp³)-H borylation enables unreactive alkanes to be transformed into valuable organoboron reagents under mild conditions and with selectivities that contrast with those of established metal-catalyzed protocols.

Nature (London, United Kingdom) 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 C3H9ClOS, 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

Shu, Chao published the artcilePhotoredox-Catalyzed Cyclobutane Synthesis by a Deboronative Radical Addition-Polar Cyclization Cascade, SDS of cas: 238088-16-9, the publication is Angewandte Chemie, International Edition (2019), 58(12), 3870-3874, database is CAplus and MEDLINE.

Photoredox-catalyzed methylcyclobutanations of boronic esters are described. The reactions proceed through single-electron transfer induced deboronative radical addition to an electron-deficient alkene followed by single-electron reduction and polar 4-exo-tet cyclization with a pendant alkyl halide. Key to the success of the methodol. was the use of easily oxidizable arylboronate complexes. Structurally diverse cyclobutanes are shown to be conveniently prepared from readily available boronic esters and a range of haloalkyl alkenes. The mild reactions display excellent functional group tolerance, and the radical addition-polar cyclization cascade also enables the synthesis of 3-, 5-, 6-, and 7-membered rings.

Angewandte Chemie, International Edition 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 C11H10O3, SDS of cas: 238088-16-9.

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

Hara, Momoko published the artcileNoncovalent Modification Strategy with Achiral Phosphoric Acid Diesters for Designing a Chiral Bronsted Base Organocatalyst, Product Details of C9H6N2O2, the publication is Bulletin of the Chemical Society of Japan (2022), 95(4), 553-555, database is CAplus.

A strategy for designing chiral Bronsted base organocatalysts through noncovalent modification of a chiral dibasic mol. with an achiral phosphoric acid diester is introduced for the first time. Such a mol. modification concept utilizing acid-base interactions may facilitate the on-demand design of asym. organocatalysts, as preliminarily demonstrated in this work.

Bulletin of the Chemical Society of Japan 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, Product Details of C9H6N2O2.

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

Moon, Lomary S. published the artcileChiral Solvating Agents for Cyanohydrins and Carboxylic Acids, SDS of cas: 13312-84-0, the publication is Journal of Organic Chemistry (2010), 75(16), 5487-5498, database is CAplus and MEDLINE.

A structure as simple as an ion pair of (R)- or (S)-mandelate and dimethylamminopyridinium ions possesses structural features that are sufficient for NMR enantiodiscrimination of cyanohydrins. Also, ¹H NMR data of cyanohydrins of known configuration obtained in the presence of the mandelate-dimethylaminopyridinium ion pair point to the existence of a correlation between chem. shifts and absolute configuration of cyanohydrins. Mandelate-DMAPH⁺ ion pair and mandelonitrile form a 1:1 complex with an association constant of 338 M^-1 (ΔG⁰, -3.4 kcal/mol) for the (R)-mandelonitrile/(R)-mandelate-DMAPH⁺ and 139 M^-1 (ΔG⁰, -2.9 kcal/mol) for the (R)-mandelonitrile/(S)-mandelate-DMAPH⁺ complex. To understand the origin of enantiodiscrimination, the geometry optimization and energy minimization of the models of ternary complexes of (S)-mandelonitrile/(R)-mandelate/DMAPH⁺ and (S)-mandelonitrile/(S)-mandelate/DMAPH⁺ complexes was performed using DFT methodol. (B3LYP) with the 6-31+G(d) basis set in Gaussian 3.0. Further, anal. of optimized mol. model obtained from theor. studies suggested that (i) DMAP may be replaced with other amines, (ii) the hydroxyl group of mandelic acid is not necessary for stabilization of ternary complex and may be replaced with other groups such as Me, (iii) the ion pair should form a stable ternary complex with any hydrogen-bond donor, provided its OH bond is sufficiently polarized, and (iv) α-H of racemic mandelic acid should also get resolved with optically pure mandelonitrile. These inferences were exptl. verified, which not only validated the proposed model but also led to development of a new chiral solvating agent for determination of ee of carboxylic acids and absolute configuration of aryl but not alkyl carboxylic acids.

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, SDS of cas: 13312-84-0.

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

Zhang, Zhi-Jun published the artcileSignificant enhancement of (R)-mandelic acid production by relieving substrate inhibition of recombinant nitrilase in toluene-water biphasic system, Computed Properties of 13312-84-0, the publication is Journal of Biotechnology (2011), 152(1-2), 24-29, database is CAplus and MEDLINE.

The enantioselective hydrolysis of mandelonitrile with whole cells of a recombinant Escherichia coli expressing nitrilase activity was severely inhibited by the substrate at high concentrations (>300 mM), which resulted in a low yield of the target product (R)-(-)-mandelic acid. To relieve the substrate inhibition and to enhance the (R)-(-)-mandelic acid productivity, eight water-organic solvent biphasic systems were attempted in this work. Toluene was found to be the most suitable solvent as the organic phase among the solvents tested. Various parameters were systematically examined and optimized in shake flasks. The phase volume ratio, buffer pH and reaction temperature were shown to be sensitive parameters affecting both the yield and the enantiopurity of product in the biphasic system. Under the optimized conditions, significant enhancement of substrate tolerance from 200 mM to 500 mM and average productivity from 179.6 g L^-1 d^-1 to 352.6 g L^-1 d^-1 were achieved. Subsequently, the biocatalytic hydrolysis of mandelonitrile was successfully carried out in a stirred reactor (2-L scale) by repeated use of the calcium alginate entrapped cells for 5 batches, affording 110.7 g (R)-(-)-mandelic acid in 98.0% ee (enantiomeric excess) and a specific production of 13.8 g (mandelic acid) g^-1 (cell), resp.

Journal of 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 C14H26O2, Computed Properties of 13312-84-0.

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