Tag: 100-200

Aluminum-Catalyzed Asymmetric Alkylations of Pyridyl-Substituted Alkynyl Ketones with Dialkylzinc Reagents was written by Friel, Donna K.;Snapper, Marc L.;Hoveyda, Amir H.. And the article was included in Journal of the American Chemical Society in 2008.Recommanded Product: 36057-44-0 This article mentions the following:

Alkylations of pyridyl-substituted ynones with Et₂Zn and Me₂Zn, promoted by amino acid-based chiral ligands in the presence of Al-based alkoxides, afford tertiary propargyl alcs. efficiently in 57% to >98% ee. Two easily accessible chiral ligands are identified as optimal for reactions of the two dialkylzinc reagents. Catalytic alkylations with Et₂Zn require a chiral ligand carrying two amino acid moieties (valine and phenylalanine) along with a p-trifluoromethylphenylamide C-terminus. In contrast, reactions with Me₂Zn are most effectively promoted in the presence of a chiral ligand containing a single amino acid (benzyl cysteine), capped by an n-butylamide. Enantiomerically enriched tertiary alcs. bearing a pyridyl and an alkyne substituent can be functionalized in a variety of manners to furnish a wide range of difficult-to-access acyclic and heterocyclic structures; two noteworthy examples are Cu-catalyzed protocols for conversion of tertiary propargyl alcs. to enantiomerically enriched tetrasubstituted allenes and bicyclic amides that bear an N-substituted quaternary carbon stereogenic center. Mechanistic models that account for the trends and enantioselectivity levels are provided. In the experiment, the researchers used many compounds, for example, 4-methoxypicolinonitrile (cas: 36057-44-0Recommanded Product: 36057-44-0).

4-methoxypicolinonitrile (cas: 36057-44-0) belongs to nitriles. The electronic structure of nitriles is very similar to that of an alkyne with the main difference being the presence of a set of lone pair electrons on the nitrogen. In addition, Nitriles can react with alkynes, which leads to an increase in carbon chain length (carbocyanation).Recommanded Product: 36057-44-0

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Iridium-Catalyzed Enantioselective C(sp³)-H Borylation of Aminocyclopropanes was written by Shi, Yongjia;Yang, Yuhuan;Xu, Senmiao. And the article was included in Angewandte Chemie, International Edition in 2022.Formula: C8H13N This article mentions the following:

Transition-metal-catalyzed regio- and stereo-controllable C-H functionalization remains a formidable challenge in asym. catalysis. Herein, we disclose the first example of iridium-catalyzed C(sp³)-H borylation of aminocyclopropanes by using simple imides as weakly coordinating directing groups under mild reaction conditions. The reaction proceeded via a six-membered iridacycle, affording a vast range of chiral aminocyclopropyl boronates. The current method features a broad spectrum of functional groups (36 examples) and high enantioselectivities (up to 99%). We also demonstrated the synthetic utility by a preparative scale C-H borylation, C-B bond transformations, and conversion of the directing group. In the experiment, the researchers used many compounds, for example, 2-Cyclohexylacetonitrile (cas: 4435-14-7Formula: C8H13N).

2-Cyclohexylacetonitrile (cas: 4435-14-7) belongs to nitriles. Nitriles are polar, as indicated by high dipole moments. As liquids, they have high relative permittivities, often in the 30s. In conventional organic reductions, nitrile is reduced by treatment with lithium aluminium hydride to the amine. Reduction to the imine followed by hydrolysis to the aldehyde takes place in the Stephen aldehyde synthesis, which uses stannous chloride in acid.Formula: C8H13N

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Photocatalytic trifluoromethoxylation of arenes and heteroarenes in continuous-flow was written by Nyuchev, Alexander V.;Wan, Ting;Cendon, Borja;Sambiagio, Carlo;Struijs, Job J. C.;Ho, Michelle;Gulias, Moises;Wang, Ying;Noe, Timothy. And the article was included in Beilstein Journal of Organic Chemistry in 2020.HPLC of Formula: 63968-85-4 This article mentions the following:

The first example of photocatalytic trifluoromethoxylation of arenes and heteroarenes, e.g., I under continuous-flow conditions is described. Application of continuous-flow microreactor technol. allowed to reduce the residence time up to 16 times in comparison to the batch procedure, while achieving similar or higher yields. In addition, the use of inorganic bases was demonstrated to increase the reaction yield under batch conditions. In the experiment, the researchers used many compounds, for example, 2-(Trifluoromethoxy)benzonitrile (cas: 63968-85-4HPLC of Formula: 63968-85-4).

2-(Trifluoromethoxy)benzonitrile (cas: 63968-85-4) belongs to nitriles. There has been no report on the microbial biosynthesis of nitriles and the physiological function of such enzymes, nor was it not even known whether aliphatic and aromatic nitriles are biological compounds or just petrochemicals. Some nitriles are manufactured by heating carboxylic acids with ammonia in the presence of catalysts. This process is used to make nitriles from natural fats and oils, the products being used as softening agents in synthetic rubbers, plastics, and textiles and for making amines.HPLC of Formula: 63968-85-4

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

An ion-pair immobilization strategy in rhodium-catalyzed asymmetric transfer hydrogenation of aromatic ketones was written by Xu, Yulong;Cheng, Tanyu;Long, Jie;Liu, Ketang;Qian, Qingqian;Gao, Fei;Liu, Guohua;Li, Hexing. And the article was included in Advanced Synthesis & Catalysis in 2012.Related Products of 101219-69-6 This article mentions the following:

A chiral diamine-based homogeneous cationic rhodium catalyst was developed and two heterogeneous cationic rhodium catalysts were obtained via the encapsulation of the homogeneous cationic rhodium catalyst within Me-SBA-15 and Me-SBA-16. All these catalysts presented excellent catalytic activities and high enantioselectivities in ultrasound-promoted asym. transfer hydrogenation of aromatic ketones and represent a successful use of the ion-pair immobilization strategy. More importantly, the encapsulation of the cationic rhodium functionality within Me-SBA-16 had an obvious high recyclability, in which the recycled catalyst could be reused nine times without significantly affecting its enantioselectivity, showing good potential in industrial application. In the experiment, the researchers used many compounds, for example, (R)-4-(1-Hydroxyethyl)benzonitrile (cas: 101219-69-6Related Products of 101219-69-6).

(R)-4-(1-Hydroxyethyl)benzonitrile (cas: 101219-69-6) belongs to nitriles. The electronic structure of nitriles is very similar to that of an alkyne with the main difference being the presence of a set of lone pair electrons on the nitrogen. In addition, Nitriles can react with alkynes, which leads to an increase in carbon chain length (carbocyanation).Related Products of 101219-69-6

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Discovery and in Vivo Evaluation of the Potent and Selective PI3Kδ Inhibitors 2-((1S)-1-((6-Amino-5-cyano-4-pyrimidinyl)amino)ethyl)-6-fluoro-N-methyl-3-(2-pyridinyl)-4-quinolinecarboxamide (AM-0687) and 2-((1S)-1-((6-Amino-5-cyano-4-pyrimidinyl)amino)ethyl)-5-fluoro-N-methyl-3-(2-pyridinyl)-4-quinolinecarboxamide (AM-1430) was written by Gonzalez-Lopez de Turiso, Felix;Hao, Xiaolin;Shin, Youngsook;Bui, Minna;Campuzano, Iain D. G.;Cardozo, Mario;Dunn, Michelle C.;Duquette, Jason;Fisher, Benjamin;Foti, Robert S.;Henne, Kirk;He, Xiao;Hu, Yi-Ling;Kelly, Ron C.;Johnson, Michael G.;Lucas, Brian S.;McCarter, John;McGee, Lawrence R.;Medina, Julio C.;Metz, Daniela;San Miguel, Tisha;Mohn, Deanna;Tran, Thuy;Vissinga, Christine;Wannberg, Sharon;Whittington, Douglas A.;Whoriskey, John;Yu, Gang;Zalameda, Leeanne;Zhang, Xuxia;Cushing, Timothy D.. And the article was included in Journal of Medicinal Chemistry in 2016.Product Details of 60025-09-4 This article mentions the following:

Optimization of the potency and pharmacokinetic profile of the lead 2,3,4-trisubstituted quinoline led to the discovery of two potent, selective, and orally bioavailable PI3Kδ inhibitors, I (AM-0687) and II (AM-1430). On the basis of their improved profile, these analogs were selected for in vivo pharmacodynamic (PD) and efficacy experiments in animal models of inflammation. The in vivo PD studies, which were carried out in a mouse pAKT inhibition animal model, confirmed the observed potency of I and II in biochem. and cellular assays. Efficacy experiments in a keyhole limpet hemocyanin model in rats demonstrated that administration of either I or II resulted in a strong dose-dependent reduction of IgG and IgM specific antibodies. The excellent in vitro and in vivo profiles of these analogs make them suitable for further development. In the experiment, the researchers used many compounds, for example, 4-Amino-6-chloropyrimidine-5-carbonitrile (cas: 60025-09-4Product Details of 60025-09-4).

4-Amino-6-chloropyrimidine-5-carbonitrile (cas: 60025-09-4) belongs to nitriles. The R-C-N bond angle in and nitrile is 180° which give a nitrile functional group a linear shape. Both the carbon and the nitrogen are sp hydridized which leaves them both with two p orbitals which overlap to form the two π bond in the triple bond. In conventional organic reductions, nitrile is reduced by treatment with lithium aluminium hydride to the amine. Reduction to the imine followed by hydrolysis to the aldehyde takes place in the Stephen aldehyde synthesis, which uses stannous chloride in acid.Product Details of 60025-09-4

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Selective deoxygenative alkylation of alcohols via photocatalytic domino radical fragmentations was written by Guo, Hong-Mei;Wu, Xuesong. And the article was included in Nature Communications in 2021.Related Products of 24056-34-6 This article mentions the following:

A one-pot strategy for deoxygenative Giese reaction of alcs. with electron-deficient alkenes, by using xanthate salts as alc.-activating groups for radical generation under visible-light photoredox conditions in the presence of triphenylphosphine were reported. The convenient generation of xanthate salts and high reactivity of sequential C-S/C-O bond homolytic cleavage enable efficient deoxygenation of primary, secondary and tertiary alcs. with diverse functionality and structure to generate the corresponding alkyl radicals, including Me radical. Moreover, chemoselective radical monodeoxygenation of diols was achieved via selective formation of xanthate salts. In the experiment, the researchers used many compounds, for example, 4-Hydroxycyclohexanecarbonitrile (cas: 24056-34-6Related Products of 24056-34-6).

4-Hydroxycyclohexanecarbonitrile (cas: 24056-34-6) belongs to nitriles. Nitriles are polar, as indicated by high dipole moments. As liquids, they have high relative permittivities, often in the 30s. Alkyl nitriles are sufficiently acidic to undergo deprotonation of the C-H bond adjacent to the CN group.Strong bases are required, such as lithium diisopropylamide and butyl lithium. The product is referred to as a nitrile anion. Related Products of 24056-34-6

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

2-Formylpyridyl Ureas as Highly Selective Reversible-Covalent Inhibitors of Fibroblast Growth Factor Receptor 4 was written by Knoepfel, Thomas;Furet, Pascal;Mah, Robert;Buschmann, Nicole;Leblanc, Catherine;Ripoche, Sebastien;Graus-Porta, Diana;Wartmann, Markus;Galuba, Inga;Fairhurst, Robin A.. And the article was included in ACS Medicinal Chemistry Letters in 2018.Electric Literature of C5H4N4 This article mentions the following:

As part of a project to identify FGFR4 selective inhibitors, scaffold morphing of a 2-formylquinoline amide hit identified series of 2-formylpyridine ureas (2-FPUs) with improved potency and physicochem. properties. In particular, tetrahydronaphthyridine urea analogs with cellular activities below 30 nM have been identified. Consistent with the hypothesized reversible-covalent mechanism of inhibition, the 2-FPUs exhibited slow binding kinetics, and the aldehyde, as the putative electrophile, could be demonstrated to be a key structural element for activity. In the experiment, the researchers used many compounds, for example, 2-Aminopyrimidine-5-carbonitrile (cas: 1753-48-6Electric Literature of C5H4N4).

2-Aminopyrimidine-5-carbonitrile (cas: 1753-48-6) belongs to nitriles. Trimerization of aromatic nitriles requires harsh reaction conditions, high temperatures, long reaction times, and pressure. Some nitriles are manufactured by heating carboxylic acids with ammonia in the presence of catalysts. This process is used to make nitriles from natural fats and oils, the products being used as softening agents in synthetic rubbers, plastics, and textiles and for making amines.Electric Literature of C5H4N4

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Equilibrium NH-acidity of substituted aminopyrimidines was written by Shkurko, O. P.;Terekhova, M. I.;Petrov, E. S.;Mamaev, V. P.;Shatenshtein, A. I.. And the article was included in Zhurnal Organicheskoi Khimii in 1981.Category: nitriles-buliding-blocks This article mentions the following:

The transmetalation method was used to determine the NH acidity (pK) of thirty-nine 2-, 4-, and 5-aminopyrimidines; the pK values ranged from 17.7 for 5-nitro-2-pyrimidinamine to 30.2 for 2-(dimethylamino)-5-pyrimidinamine. Comparison with the pK of aniline showed that the ring N atoms had an acidifying effect in the order 4-aza ≫ 2-aza > 3-aza. LFER of the pK vs. NMR chem. shifts, and inductive or resonance substituent constants were described. In the experiment, the researchers used many compounds, for example, 2-Aminopyrimidine-5-carbonitrile (cas: 1753-48-6Category: nitriles-buliding-blocks).

2-Aminopyrimidine-5-carbonitrile (cas: 1753-48-6) belongs to nitriles. Nitrile compounds can be prepared by the incorporation of a cyanide source through C–C bond formation or by dehydration of primary carboxamides. Asymmetric bioreduction of nitriles is an attractive route to produce optically active nitriles as current metal-catalyzed hydrogenations tend to have low reactivity.Category: nitriles-buliding-blocks

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

An improved synthesis of homoproline and derivatives was written by Shuman, Robert T.;Ornstein, Paul L.;Paschal, Jonathan W.;Gesellchen, Paul D.. And the article was included in Journal of Organic Chemistry in 1990.HPLC of Formula: 36057-44-0 This article mentions the following:

Homoproline derivatives I (R = 3-Me, 4-Me, 6-Me, 4-Et, 4-OMe, 4-CMe₃) were prepared from the corresponding pyridines II in 4 steps. A key step was the treatment of N-oxides III (R = same) with Me₃SiCN and Me₂NCOCl in CH₂Cl₂ to give nitriles IV (R = same). 5,6-Benzohomoprolines V (R¹ = H, Me) were also prepared In the experiment, the researchers used many compounds, for example, 4-methoxypicolinonitrile (cas: 36057-44-0HPLC of Formula: 36057-44-0).

4-methoxypicolinonitrile (cas: 36057-44-0) belongs to nitriles. Nitrile function is a very important functional group because it can be manipulated to other functional groups such as carboxylic acid by hydrolysis or amine by reduction, respectively. Alkyl nitriles are sufficiently acidic to undergo deprotonation of the C-H bond adjacent to the CN group.Strong bases are required, such as lithium diisopropylamide and butyl lithium. The product is referred to as a nitrile anion. HPLC of Formula: 36057-44-0

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Research in the heterocyclic series. VII. Orientation of nitro derivatives of α-substituted thiophenes, pyrroles, and N-methylpyrroles was written by Tirouflet, Jean;Fournari, Pierre. And the article was included in Bulletin de la Societe Chimique de France in 1963.COA of Formula: C5H2N2O2S This article mentions the following:

The ratios of the isomeric mono-NO₂ derivatives formed under various conditions from 2-substituted-thiophenes (I), pyrroles (II), and 1-methylpyrroles (III) were determined polarographically and found to be dependent on the nature of the α-substituent and the hetero atom. In the thiophene series, the substituent exerts a more pronounced effect than in the pyrrole series and the 1-methylpyrrole series. The N-methylation of pyrroles increases the reactivity of the β-position. The nitrations in the II and III series were performed by nitrating the appropriate heterocyclic substrate (1-4 g.) by the methods described previously (loc. cit.), pouring the mixture onto 10-50 g. ice, and then polarographing the solution (if necessary after the addition of AcOH or aqueous EtOH); the half-wave potentials were determined for the following I (2-substituent, pH, and half-wave potentials in neg. v. of the 5- and 4-NO₂ derivatives given): H, 3.1, 0.30, 0.40; NO₂, 3.1, 0.06, 0.13; CHO, 9.1, 0.35, 0.57 (at pH 4.2, the 5-NO₂ derivative showed 2 waves at -0.16 and -0.31 v., resp., and the 4-NO₂ derivative 1 at -0.34 v.); Ac, 10.2, 0.41, 0.61; CN, 3.1, 0.14, 0.29; CO₂H, 4.2, 0.23, 0.42. The same delta were determined for the following II (same data given): H, 3.1, 0.54, 0.67; NO₂, 2, 0.07, 0.18; CHO, 2, 0.15, 0.50; Ac, 3.1, 0.24, 0.51; CN, 3.1, 0.14, 0.29; CO₂H, 3.1, 0.31, 0.60. The same data were determined for the following III (same data given): H, 5.4, 0.59, 0.68; NO₂, 3.1, 0.08, 0.25; CHO, 10.2, 0.55, 0.76; Ac, 10.2, 0.60, 0.80; CN, 5.2, 0.37, 0.53; CO₂H, 3.1, 0.25, 0.52. The % content of the 4-NO₂ derivatives (IV) in the nitration products of the following I was determined polarographically (2-substituent and % IV given): H 5, NO₂ 80, CHO 75, Ac 52, CN 43, CO₂H 31, CH(OAe)₂ 14. The % content of the IV from the following II was determined (same data given): H 9, NO₂ 67, CHO 59, Ac 57, CN 42, CO₂H, 55. The % content of the IV from the following III was deed. (same data given): II 43, NO₂ 70, CHO 80, Ac 68, CN 65, CO₂H 68. The effect of various reaction media on the composition of the product was determined in a series of runs with I. 2-Thiophenecarboxaldehyde with HNO₃H₂SO₄ (free CHO group) yielded preferentially the 4-NO₂ derivative, while nitration in Ac₂O [CHO group present as CH(OAc)₂] favored the formation of the 5-NO₂ derivative In the experiment, the researchers used many compounds, for example, 4-Nitrothiophene-2-carbonitrile (cas: 42137-24-6COA of Formula: C5H2N2O2S).

4-Nitrothiophene-2-carbonitrile (cas: 42137-24-6) belongs to nitriles. There has been no report on the microbial biosynthesis of nitriles and the physiological function of such enzymes, nor was it not even known whether aliphatic and aromatic nitriles are biological compounds or just petrochemicals. Nitriles are susceptible to hydrogenation over diverse metal catalysts. The reaction can afford either the primary amine (RCH2NH2) or the tertiary amine ((RCH2)3N), depending on conditions.COA of Formula: C5H2N2O2S

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts