Author: Jessica.F

Highly active cooperative Lewis acid-ammonium salt catalyst for enantioselective hydroboration of ketones was written by Titze, Marvin;Heitkaemper, Juliane;Junge, Thorsten;Kaestner, Johannes;Peters, Rene. And the article was included in Angewandte Chemie, International Edition in 2021.Computed Properties of C9H9NO This article mentions the following:

Enantiopure secondary alcs. are fundamental high-value synthetic building blocks. One of the most attractive ways to get access to this compound class is the catalytic hydroboration. We describe a new concept for this reaction type that allowed for exceptional catalytic turnover numbers (up to 15 400), which were increased by around 1.5-3 orders of magnitude compared to the most active catalysts previously reported. In our concept an aprotic ammonium halide moiety cooperates with an oxo philic Lewis acid within the same catalyst mol. Control experiments reveal that both catalytic centers are essential for the observed activity. Kinetic, spectroscopic and computational studies show that the hydride transfer is rate limiting and proceeds via a concerted mechanism, in which hydride at Boron is continuously displaced by iodide, reminiscent to an S_N2 reaction. The catalyst, which is accessible in high yields in few steps, was found to be stable during catalysis, readily recyclable and could be reused 10 times still efficiently working. In the experiment, the researchers used many compounds, for example, (R)-4-(1-Hydroxyethyl)benzonitrile (cas: 101219-69-6Computed Properties of C9H9NO).

(R)-4-(1-Hydroxyethyl)benzonitrile (cas: 101219-69-6) belongs to nitriles. Nitrile carbon shifts are in the range of 115�25 ppm whereas in isonitriles the shifts are around 155�65 ppm. Industrially, the main methods for producing nitriles are ammoxidation and hydrocyanation. Both routes are green in the sense that they do not generate stoichiometric amounts of salts.Computed Properties of C9H9NO

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A remarkably effective catalyst for the asymmetric transfer hydrogenation of aromatic ketones in water and air was written by Wu, Xiaofeng;Vinci, Daniele;Ikariya, Takao;Xiao, Jiangliang. And the article was included in Chemical Communications (Cambridge, United Kingdom) in 2005.Synthetic Route of C9H9NO This article mentions the following:

A Rh(III) complex generated in situ from [Cp^*RhCl₂]₂ and (1R,2R)-N-(p-toluenesulfonyl)-1,2-cyclohexanediamine (TsCYDN) serves as a remarkably effective, robust catalyst for the asym. transfer hydrogenation of aromatic ketones by HCOONa in water in air, affording alcs. in up to 99% ee. In the experiment, the researchers used many compounds, for example, (R)-4-(1-Hydroxyethyl)benzonitrile (cas: 101219-69-6Synthetic Route of C9H9NO).

(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).Synthetic Route of C9H9NO

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Synthesis of prenylated benzaldehydes and their use in the synthesis of analogs of licochalcone A was written by Kromann, Hasse;Larsen, Mogens;Boesen, Thomas;Schonning, Kristian;Nielsen, Simon Feldbaek. And the article was included in European Journal of Medicinal Chemistry in 2004.Synthetic Route of C11H13NO This article mentions the following:

A generally applicable synthesis of prenylated aromatic compounds exemplified by prenylated benzaldehydes starting from readily available acetophenones was described. The synthesized benzaldehydes were used to prepare a number of novel analogs, such as I (R = OH, R¹ = H, Cl, OMe; R = H, R¹ = H, OH; R = OMe, R¹ = OH, OMe), of Licochalcone A, a known antibacterial compound, and for the exploration of the pharmacophoric elements that are essential for the antibacterial activity. It was shown that the hydroxyl group in the A ring is essential for the activity and that the hydroxyl group in the B ring has no influence on the antibacterial effect of Licochalcone A. Furthermore, it is shown that the prenyl group at the position 5 of the B ring also has a dominating influence on the activity. This aliphatic group can be replaced by other lipophilic long chained substituents in order to maintain the activity. In the experiment, the researchers used many compounds, for example, 2-(4-Methoxyphenyl)-2-methylpropanenitrile (cas: 5351-07-5Synthetic Route of C11H13NO).

2-(4-Methoxyphenyl)-2-methylpropanenitrile (cas: 5351-07-5) 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. 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.Synthetic Route of C11H13NO

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Palladium-Catalyzed Late-Stage Direct Arene Cyanation was written by Zhao, Da;Xu, Peng;Ritter, Tobias. And the article was included in Chem in 2019.Recommanded Product: 3-(tert-Butyl)benzonitrile This article mentions the following:

The first general late-stage aryl C-H cyanation with broad substrate scope and functional-group tolerance was reported. The reaction was enabled by a dual-ligand combination of quinoxaline and an amino acid-derived ligand. The method was applicable to direct cyanation of several marketed small-mol. drugs, common pharmacophores and organic dyes. In the experiment, the researchers used many compounds, for example, 3-(tert-Butyl)benzonitrile (cas: 154532-34-0Recommanded Product: 3-(tert-Butyl)benzonitrile).

3-(tert-Butyl)benzonitrile (cas: 154532-34-0) belongs to nitriles. Nitrile carbon shifts are in the range of 115�25 ppm whereas in isonitriles the shifts are around 155�65 ppm. 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.Recommanded Product: 3-(tert-Butyl)benzonitrile

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2-(2-Thienyl)-5,6-dihydroxy-4-carboxypyrimidines as Inhibitors of the Hepatitis C Virus NS5B Polymerase: Discovery, SAR, Modeling, and Mutagenesis was written by Koch, Uwe;Attenni, Barbara;Malancona, Savina;Colarusso, Stefania;Conte, Immacolata;Di Filippo, Marcello;Harper, Steven;Pacini, Barbara;Giomini, Claudia;Thomas, Steven;Incitti, Ilario;Tomei, Licia;De Francesco, Raffaele;Altamura, Sergio;Matassa, Victor G.;Narjes, Frank. And the article was included in Journal of Medicinal Chemistry in 2006.Recommanded Product: 42137-24-6 This article mentions the following:

Infections caused by hepatitis C virus (HCV) are a significant world health problem for which novel therapies are in urgent demand. The polymerase of HCV is responsible for the replication of viral RNA. The authors recently disclosed dihydroxypyrimidine carboxylates as novel, reversible inhibitors of the HCV NS5B polymerase. This series was further developed into 5,6-dihydroxy-2-(2-thienyl)pyrimidine-4-carboxylic acids such as (I) (EC₅₀ 9.3 μM), which now show activity in the cell-based HCV replication assay. The structure-activity relation of these inhibitors is discussed in the context of their physicochem. properties and of the polymerase crystal structure. We also report the results of mutagenesis experiments which support the proposed binding model, which involves pyrophosphate-like chelation of the active site Mg ions. In the experiment, the researchers used many compounds, for example, 4-Nitrothiophene-2-carbonitrile (cas: 42137-24-6Recommanded Product: 42137-24-6).

4-Nitrothiophene-2-carbonitrile (cas: 42137-24-6) 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. Industrially, the main methods for producing nitriles are ammoxidation and hydrocyanation. Both routes are green in the sense that they do not generate stoichiometric amounts of salts.Recommanded Product: 42137-24-6

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Nitrile – Wikipedia,
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Trigonal-Bipyramidal Copper(II) Complexes with Symmetric and Unsymmetric Tripodal Tetramine Ligands was written by Dittler-Klingemann, Andreas M.;Hahn, F. Ekkehardt. And the article was included in Inorganic Chemistry in 1996.Quality Control of 3,3′,3”-Nitrilotripropanenitrile This article mentions the following:

The syntheses of the aliphatic tripodal tetramine ligands N(CH₂CH₂CH₂NH₂)₃ (1), N[(CH₂CH₂CH₂NH₂)₂(CH₂CH₂NH₂)] (2), and N[(CH₂CH₂CH₂NH₂)(CH₂CH₂NH₂)₂] (3) are reported. The tripodal N₄– ligands 1–3 react with Cu(OH)₂ in H₂O to give blue Cu(II) complexes. Addition of NH₄PF₆ to such solutions yields [Cu(N₄)(NH₃)](PF₆)₂ [4; N₄ = 1, 4a; N₄ = 2, 4b; N₄ = 3, 4c]. The mol. structures of complexes 4a–c were determined by x-ray diffraction. All three complexes can be crystallized from H₂O. Selected crystallog. details are as follows 4a [4b] {4c}: formula C₉H₂₇CuF₁₂N₅P₂ [C₈H₂₅CuF₁₂N₅P₂] {C₇H₂₃CuF₁₂N₅P₂}, M = 558.82 [544.79] MLL {530.76} amu, monoclinic [monoclinic] {orthorhombic}, space group P2₁/c [C2/c] {P2₁2₁2}, a = 8.9519(14) [30.181(6)] {15.075(5)} Å, b = 16.803(3) [8.914(3)] {12.2939(14)} Å, c 13.834(2) [14.253(4)] {10.064(2)} , β = 94.183(12) [93.76(2)] {90.0}°, V = 2075.3(10) [3826(3)] {1865.2(12)} ų, Z = 4 [8] {4}, R = 5.10 [3.42] {4.32}, R_w = 6.67 [5.12] {5.23} for 2480 [2137] {1533} absorption corrected structure factors F_o² â‰?3σ(F_o²) and 262 [255] {245} refined parameters. The complex dications in 4a–c exhibit a trigonal-bipyramidal geometry with the tertiary N of the tripodal ligand and the NH₃ N in the axial positions. Complexes with the unsym. ligands 2 and 3 possess both five and six membered chelate rings. Depending on the ligand, the size of the cavity for the NH₃ ligand increases from 4a to 4c. This leads to a shortening of the Cu-NH₃ bond length with the shortest bond of this type observed for 4c. In the experiment, the researchers used many compounds, for example, 3,3′,3”-Nitrilotripropanenitrile (cas: 7528-78-1Quality Control of 3,3′,3”-Nitrilotripropanenitrile).

3,3′,3”-Nitrilotripropanenitrile (cas: 7528-78-1) belongs to nitriles. Nitriles are polar, as indicated by high dipole moments. As liquids, they have high relative permittivities, often in the 30s. Asymmetric bioreduction of nitriles is an attractive route to produce optically active nitriles as current metal-catalyzed hydrogenations tend to have low reactivity.Quality Control of 3,3′,3”-Nitrilotripropanenitrile

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Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Trigonal-Bipyramidal Copper(II) Complexes with Symmetric and Unsymmetric Tripodal Tetramine Ligands was written by Dittler-Klingemann, Andreas M.;Hahn, F. Ekkehardt. And the article was included in Inorganic Chemistry in 1996.Quality Control of 3,3′,3”-Nitrilotripropanenitrile This article mentions the following:

The syntheses of the aliphatic tripodal tetramine ligands N(CH₂CH₂CH₂NH₂)₃ (1), N[(CH₂CH₂CH₂NH₂)₂(CH₂CH₂NH₂)] (2), and N[(CH₂CH₂CH₂NH₂)(CH₂CH₂NH₂)₂] (3) are reported. The tripodal N₄– ligands 1–3 react with Cu(OH)₂ in H₂O to give blue Cu(II) complexes. Addition of NH₄PF₆ to such solutions yields [Cu(N₄)(NH₃)](PF₆)₂ [4; N₄ = 1, 4a; N₄ = 2, 4b; N₄ = 3, 4c]. The mol. structures of complexes 4a–c were determined by x-ray diffraction. All three complexes can be crystallized from H₂O. Selected crystallog. details are as follows 4a [4b] {4c}: formula C₉H₂₇CuF₁₂N₅P₂ [C₈H₂₅CuF₁₂N₅P₂] {C₇H₂₃CuF₁₂N₅P₂}, M = 558.82 [544.79] MLL {530.76} amu, monoclinic [monoclinic] {orthorhombic}, space group P2₁/c [C2/c] {P2₁2₁2}, a = 8.9519(14) [30.181(6)] {15.075(5)} Å, b = 16.803(3) [8.914(3)] {12.2939(14)} Å, c 13.834(2) [14.253(4)] {10.064(2)} , β = 94.183(12) [93.76(2)] {90.0}°, V = 2075.3(10) [3826(3)] {1865.2(12)} ų, Z = 4 [8] {4}, R = 5.10 [3.42] {4.32}, R_w = 6.67 [5.12] {5.23} for 2480 [2137] {1533} absorption corrected structure factors F_o² ≥ 3σ(F_o²) and 262 [255] {245} refined parameters. The complex dications in 4a–c exhibit a trigonal-bipyramidal geometry with the tertiary N of the tripodal ligand and the NH₃ N in the axial positions. Complexes with the unsym. ligands 2 and 3 possess both five and six membered chelate rings. Depending on the ligand, the size of the cavity for the NH₃ ligand increases from 4a to 4c. This leads to a shortening of the Cu-NH₃ bond length with the shortest bond of this type observed for 4c. In the experiment, the researchers used many compounds, for example, 3,3′,3”-Nitrilotripropanenitrile (cas: 7528-78-1Quality Control of 3,3′,3”-Nitrilotripropanenitrile).

3,3′,3”-Nitrilotripropanenitrile (cas: 7528-78-1) belongs to nitriles. Nitriles are polar, as indicated by high dipole moments. As liquids, they have high relative permittivities, often in the 30s. Asymmetric bioreduction of nitriles is an attractive route to produce optically active nitriles as current metal-catalyzed hydrogenations tend to have low reactivity.Quality Control of 3,3′,3”-Nitrilotripropanenitrile

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Some amine derivatives of acrylonitrile was written by Wiedeman, O. F.;Montgomery, W. H.. And the article was included in Journal of the American Chemical Society in 1945.Recommanded Product: 3,3′,3”-Nitrilotripropanenitrile This article mentions the following:

CH₂:CHCN (I) (12, 000 cc.), added dropwise to 6500 cc. 28% NH₄OH at 30°, gives 1.7% (of the I used) of NCCH₂CH₂NH₂ (II), 88.5% of NH(CH₂CH₂CN)₂ (III), and 6% of N(CH₂CH₂CN)₃ (IV), m. 99°; 880 cc. of I, and 500 cc. NH₄OH give 5.8% of II, 83.5% of III, and 1% of IV; 6000 cc. of I and 36, 000 cc. NH₄OH give 23.9% of II, 58.9% of III, and 3.3% of IV. Many samples of IV, which remained unchanged at room temperature for several months, decomposed within 24 h. for no apparent reason; no effective stabilizer was found and CO₂ apparently accelerated decomposition III is quite stable but some decomposition occurs on distillation at 140-60°/2-5 mm. IV is recovered from the residue of the vacuum distillation of II and III by extraction with hot H₂O. Catalytic reduction of II in lots of 5-10 mol in the presence of 1.1 mol of anhydrous NH₃ and 2-3 g. Raney Ni (per mole of amine) at pressures of 50-250 atm. for 5-10 h. at 90-125° gives 54% of NH₂(CH₂)₃NH₂ (V), 12% of (H₂NCH₂CH₂CH₂)₂NH (VI), b_2-3 100°, d²⁰ 0.9307, d²⁵ 0.9268, n_D²⁵ 1.4910, and 3% of (H₂NCH₂CH₂CH₂)₃N (VII), b_2-3 140-50°, d²⁰ 0.9591, d²⁵ 0.9552, n_D²⁵ 1.4910. III gives 14% of V, 58% of VI, and 13% of VII. A mixture of 30% II, 65% III, and 4% IV gives 28% of V, 42% of VI, and 13% of VII. I and (CH₂)₂O give (NCCH₂CH₂)₂O, b_2-3 140°, d²⁰ 1.0497, d²⁵ 1.0457, n_D²⁵ 1.4404; reduction in the presence of NH₃ at 110-15° and 100 atm. for 2 h. yielded 25-30% of low-boiling impurities (some PrNH₂), 35-40% of H₂N(CH₂)₃OH, b_2-3 60°, d²⁰ 0.9832, d²⁵ 0.9794, n_D²⁵ 1.4597, and 20% of (H₂NCH₂CH₂CH₂)₂O, b₃ 130-40°, d²⁰ 0.9723, d²⁵ 0.9685, n_D²⁵ 1.4780; the residue was 15%. In the experiment, the researchers used many compounds, for example, 3,3′,3”-Nitrilotripropanenitrile (cas: 7528-78-1Recommanded Product: 3,3′,3”-Nitrilotripropanenitrile).

3,3′,3”-Nitrilotripropanenitrile (cas: 7528-78-1) 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. Recommanded Product: 3,3′,3”-Nitrilotripropanenitrile

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Radical C-H Trifluoromethoxylation of (Hetero)arenes with Bis(trifluoromethyl)peroxide was written by Dix, Stefan;Golz, Paul;Schmid, Jonas R.;Riedel, Sebastian;Hopkinson, Matthew N.. And the article was included in Chemistry – A European Journal in 2021.Computed Properties of C8H4F3NO This article mentions the following:

Herein, bis(trifluoromethyl)peroxide (BTMP, CF₃OOCF₃) as a practical and efficient trifluoromethoxylating reagent, which easily accessible from inexpensive bulk chems. was introduced. Using either visible light photoredox or TEMPO catalysis, trifluoromethoxylated arenes could be prepared in good yields under mild conditions directly from unactivated aromatics Moreover, TEMPO catalysis allowed for the one-step synthesis of valuable pyridine derivatives, which was previously prepared via multi-step approaches. In the experiment, the researchers used many compounds, for example, 2-(Trifluoromethoxy)benzonitrile (cas: 63968-85-4Computed Properties of C8H4F3NO).

2-(Trifluoromethoxy)benzonitrile (cas: 63968-85-4) belongs to nitriles. Nitrile carbon shifts are in the range of 115–125 ppm whereas in isonitriles the shifts are around 155–165 ppm. 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.Computed Properties of C8H4F3NO

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Base-mediated cascade amidination/N-alkylation of amines by alcohols was written by Zhang, Chunyan;Liang, Zuyu;Lu, Fenghong;Jia, Xiaofei;Zhang, Guoying;Hu, Mao-Lin. And the article was included in Chemical Communications (Cambridge, United Kingdom) in 2020.Electric Literature of C14H12N2 This article mentions the following:

A base-mediated cascade amidination/N-alkylation reaction of amines by alcs. was developed. For the first time, nitriles was identified as an efficient and benign water acceptor reagent in N-alkylation. Notably, the procedure tolerates a series of functional groups, such as methoxyl, halo, vinyl and hetero groups, providing a convenient method to construct different substituted diamino compounds, ¹⁵N labeled amine and was scaled up to 1 mol scale offering 138.7 g of the desired product in good yield in one-pot. Mechanistic studies provided strong evidence for the amidination of amines with nitriles facilitated by t-BuOK. In the experiment, the researchers used many compounds, for example, 4-(Benzylamino)benzonitrile (cas: 10282-32-3Electric Literature of C14H12N2).

4-(Benzylamino)benzonitrile (cas: 10282-32-3) 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. 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 C14H12N2

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts