Month: January 2023

Asymmetric transfer hydrogenation of ketones promoted by manganese(I) pre-catalysts supported by bidentate aminophosphines was written by Azouzi, Karim;Bruneau-Voisine, Antoine;Vendier, Laure;Sortais, Jean-Baptiste;Bastin, Stephanie. And the article was included in Catalysis Communications in 2020.Formula: C9H9NO This article mentions the following:

A series of com. available chiral amino-phosphines, in combination with Mn(CO)₅Br, was evaluated for the asym. reduction of ketones to secondary alcs. RCH(OH)R¹ [R = c-hexyl, Ph, 1-naphthyl, etc.; R¹ = Me, Et, i-Pr, etc.] using isopropanol as hydrogen source. With the most selective ligand, the corresponding manganese complex was synthesized and fully characterized. A series of ketones was hydrogenated in the presence of 0.5 mol% of the manganese pre-catalyst affording the chiral alcs. in high yields with enantiomeric excesses up to 99%. In the experiment, the researchers used many compounds, for example, (R)-4-(1-Hydroxyethyl)benzonitrile (cas: 101219-69-6Formula: C9H9NO).

(R)-4-(1-Hydroxyethyl)benzonitrile (cas: 101219-69-6) belongs to nitriles. Trimerization of aromatic nitriles requires harsh reaction conditions, high temperatures, long reaction times, and pressure. 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.Formula: C9H9NO

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Solubility measurement and modelling of ethyl 5-amino-4-cyano-3-(2-ethoxy-2-oxoethyl)-2-thiophenecarboxylate in four groups mixed solvents was written by Li, Xinbao;Han, Shuo;Zhao, Hongkun. And the article was included in Journal of Chemical Thermodynamics in 2016.Synthetic Route of C12H14N2O4S This article mentions the following:

The solubility of Et 5-amino-4-cyano-3-(2-ethoxy-2-oxoethyl)-2-thiophenecarboxylate (ACET) in binary (acetone + methanol), (acetone + ethanol), (acetone + 1-butanol) and (acetone + isopropanol) solvent mixtures was investigated by the isothermal dissolution equilibrium method under 101.3 kPa. This study was carried out at different mass fractions of acetone ranging from 0.1 to 0.9 at T = (273.15-318.15) K. For the nine groups with each solvent mixture studied, the solubility of ACET in the mixed solutions increased with increasing temperature and mass fraction acetone. At the same temperature and mass fraction of acetone, the solubility of ACET was greater in (acetone + methanol) than in the other three solvent mixtures The exptl. solubility values were correlated by three co-solvency models (Jouyban-Acree model, van’t Hoff-Jouyban-Acree model and Apelblat- Jouyban-Acree model). The relative average deviations (RAD) and the root-mean-square deviations (RMSD) were all less than 1.49 × 10^-2 and 8.99 × 10^-4, resp. The Apelblat-Jouyban-Acree model provided best representation of the exptl. solubility Furthermore, the standard molar enthalpy of the ACET during the dissolving process (Δ_solH^o) was also derived in this work, and the results showed that the dissolution process is endothermic. The exptl. solubility and the models used in this work would be helpful in purifying of ACET from its crude mixtures In the experiment, the researchers used many compounds, for example, Ethyl 5-amino-4-cyano-3-(2-ethoxy-2-oxoethyl)thiophene-2-carboxylate (cas: 58168-20-0Synthetic Route of C12H14N2O4S).

Ethyl 5-amino-4-cyano-3-(2-ethoxy-2-oxoethyl)thiophene-2-carboxylate (cas: 58168-20-0) 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. 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.Synthetic Route of C12H14N2O4S

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Asymmetric Synthesis of the Antiarrhythmia Agent d-Sotalol was written by Brodfuehrer, Paul R.;Smith, Patrick;Dillon, John L.;Vemishetti, Purushotham. And the article was included in Organic Process Research & Development in 1997.HPLC of Formula: 101219-69-6 This article mentions the following:

A chiral synthesis of d-Sotalol (I) was developed starting from com. available 4′-(chloroacetyl)methanesulfonanilide. Key step was the asym. reduction of the ketone by BH₃-THF in the presence of a chiral borane. In the experiment, the researchers used many compounds, for example, (R)-4-(1-Hydroxyethyl)benzonitrile (cas: 101219-69-6HPLC of Formula: 101219-69-6).

(R)-4-(1-Hydroxyethyl)benzonitrile (cas: 101219-69-6) 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. 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.HPLC of Formula: 101219-69-6

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Dual Ligand-Enabled Nondirected C-H Cyanation of Arenes was written by Chen, Hao;Mondal, Arup;Wedi, Philipp;van Gemmeren, Manuel. And the article was included in ACS Catalysis in 2019.Reference of 154532-34-0 This article mentions the following:

Aromatic nitriles are key structural units in organic chem. and, therefore, highly attractive targets for C-H activation. Herein, the development of an arene-limited, nondirected C-H cyanation based on the use of two cooperatively acting com. available ligands is reported. The reaction enables the cyanation of arenes by C-H activation in the absence of directing groups and is therefore complementary to established approaches. In the experiment, the researchers used many compounds, for example, 3-(tert-Butyl)benzonitrile (cas: 154532-34-0Reference of 154532-34-0).

3-(tert-Butyl)benzonitrile (cas: 154532-34-0) 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. 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.Reference of 154532-34-0

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Proton magnetic resonance (NMR) of thiophenes. VIII. Coupling constants in disubstituted thiophenes was written by Hoffman, Ragnar A.;Gronowitz, Salo. And the article was included in Arkiv foer Kemi in 1960.COA of Formula: C5H2N2O2S This article mentions the following:

The ring coupling constants in 19 2,5-, 17 2,3-, 18 2,4-, and 11 3,4-disubstituted thiophenes are reported. The values are: J₃₄ = 3.45-4.35; J₄₅ = 4.90-5.80; J₃₅ = 1.25-1.70; and J₂₅ = 3.20-3.65 cycles/sec., all values ±0.15 cycles/sec. These values were compared with the spin couplings of other monocyclic aromatic systems. Couplings between the side-chain proton and ring protons were observed in methylthiophenes, thiophene aldehydes, and thiophene thiols. These side-chain couplings have values of J_CH3-3 = 1.00-1.15, J_CH3-4 = 0.2-0.5 and J_CH3-5 <0.4 in 2-methylthiophenes; J_CH3-2= 0.9-1.25, J_CH34 ≈ J_CH3-5 =0.4-0.5 in 3-methylthiophenes; J_CHO-5 = 1.05-1.40 in 2-thiophenealdehydes; J_CHO-5 = (<0.4)-0.80 in 3-thiophenealdehydes; J_SH-3 = 1.4-1.60, J_SH-5= 0.90-1.0 in 2-thiophenethiols; J_SH-2 = 0.65-1.05, J_SH-5 ≤ 0.3 cycles/sec. in 3-thiophenethiols. Couplings between protons of different side-chains were observed in the 3- and 5-methyl-2-thiophenethiols and in 2-methyl-3-thiophenethiol, but not in 3-methyl-4-thiophenethiol or any methyl-substituted thiophene aldehyde. An explanation for these observations isproposed. 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. 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. 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. COA of Formula: C5H2N2O2S

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

A kinetic study of the N-bromosuccinimide bromination of some 4-substituted 3-cyanotoluenes was written by Fisher, T. H.;Meierhoefer, A. W.. And the article was included in Journal of Organic Chemistry in 1978.Application In Synthesis of 5-Methyl-2-nitrobenzonitrile This article mentions the following:

The log of the relative rates of the N-bromosuccinimide bromination of I (R = H, MeO, PhN₂, Me, Ph, iodo, Br, Cl, F, Ac, CN, NO₂) were linear in σ⁺ with ρ 1.13 ± 0.12. The substituent effects were discussed in terms of polar transition states and bond dissociation energies. The electron withdrawing substituents exhibited extra-resonance in this free radical reaction. In the experiment, the researchers used many compounds, for example, 5-Methyl-2-nitrobenzonitrile (cas: 64113-86-6Application In Synthesis of 5-Methyl-2-nitrobenzonitrile).

5-Methyl-2-nitrobenzonitrile (cas: 64113-86-6) 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. 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.Application In Synthesis of 5-Methyl-2-nitrobenzonitrile

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

5,6-Dihydroxypyrimidine Scaffold to Target HIV-1 Nucleocapsid Protein was written by Malancona, Savina;Mori, Mattia;Fezzardi, Paola;Santoriello, Marisabella;Basta, Andreina;Nibbio, Martina;Kovalenko, Lesia;Speziale, Roberto;Battista, Maria Rosaria;Cellucci, Antonella;Gennari, Nadia;Monteagudo, Edith;Di Marco, Annalise;Giannini, Alessia;Sharma, Rajhans;Pires, Manuel;Real, Eleonore;Zazzi, Maurizio;Dasso Lang, Maria Chiara;De Forni, Davide;Saladini, Francesco;Mely, Yves;Summa, Vincenzo;Harper, Steven;Botta, Maurizio. And the article was included in ACS Medicinal Chemistry Letters in 2020.Formula: C7H6N2O This article mentions the following:

The HIV-1 nucleocapsid (NC) protein is a small basic DNA and RNA binding protein that is absolutely necessary for viral replication and thus represents a target of great interest to develop new anti-HIV agents. Moreover, the highly conserved sequence offers the opportunity to escape the drug resistance (DR) that emerged following the highly active antiretroviral therapy (HAART) treatment. On the basis of our previous research, nordihydroguaiaretic acid 1 acts as a NC inhibitor showing moderate antiviral activity and suboptimal drug-like properties due to the presence of the catechol moieties. A bioisosteric catechol replacement approach led us to identify the 5-dihydroxypyrimidine-6-carboxamide substructure as a privileged scaffold of a new class of HIV-1 NC inhibitors. Hit validation efforts led to the identification of optimized analogs, as represented by compound 28, showing improved NC inhibition and antiviral activity as well as good ADME and PK properties. In the experiment, the researchers used many compounds, for example, 4-methoxypicolinonitrile (cas: 36057-44-0Formula: C7H6N2O).

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. Nitrile groups in organic compounds can undergo a variety of reactions depending on the reactants or conditions. A nitrile group can be hydrolyzed, reduced, or ejected from a molecule as a cyanide ion.Formula: C7H6N2O

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

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.Safety of 3-Methylthiophene-2-carbonitrile 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, 3-Methylthiophene-2-carbonitrile (cas: 55406-13-8Safety of 3-Methylthiophene-2-carbonitrile).

3-Methylthiophene-2-carbonitrile (cas: 55406-13-8) 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. 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.Safety of 3-Methylthiophene-2-carbonitrile

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Conversions of carbonyl compounds via their polymeric sulfonylhydrazones into alkenes, alkanes, and nitriles was written by Kamogawa, Hiroyoshi;Kanzawa, Asami;Kadoya, Masahiro;Naito, Takeshi;Nanasawa, Masato. And the article was included in Bulletin of the Chemical Society of Japan in 1983.Name: 2-Cyclohexylacetonitrile This article mentions the following:

RR¹CO [R = H, R¹ = (CH₂)₅Me, Ph, cyclohexyl; R = Me, R¹ = Ph, CH₂CH₂Ph; R = R¹ = Ph, CH₂Ph; RR¹ = (CH₂)₅, (CH₂)₁₁, (CH₂)₂CHMe; RR¹CO = camphor] reacted with hydrazine bound to sulfonated styrene-divinylbenzene copolymer to form polymer-bound sulfonylhydrazones (I). I reacted with alkali to give alkenes, with NaBH₄ or LiAlH₄ to give RCH_iR¹, and with KCN to give RR¹CHCN. The extent of the reaction depended on the type of resin and the bulk of RR¹CO. In the experiment, the researchers used many compounds, for example, 2-Cyclohexylacetonitrile (cas: 4435-14-7Name: 2-Cyclohexylacetonitrile).

2-Cyclohexylacetonitrile (cas: 4435-14-7) belongs to nitriles. Trimerization of aromatic nitriles requires harsh reaction conditions, high temperatures, long reaction times, and pressure. Nitrile groups in organic compounds can undergo a variety of reactions depending on the reactants or conditions. A nitrile group can be hydrolyzed, reduced, or ejected from a molecule as a cyanide ion.Name: 2-Cyclohexylacetonitrile

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Synthesis, crystal structures and biological activity of two enantiomeric 2-trifluoromethylthieno[2,3-d]pyrimidin-4-amine derivatives was written by Gao, Hui;Fu, Ju;Zhao, Ming-juan;Song, Xin-jian;Yang, Ping;Zheng, Yin. And the article was included in Chinese Journal of Structural Chemistry in 2015.Recommanded Product: 2-Amino-5,6-dihydro-4H-cyclopenta[b]thiophene-3-carbonitrile This article mentions the following:

Two enantiomeric 2-trifluoromethyl-6,7-dihydro-5H-cyclopenta[4,5]thieno[2,3-d]pyrimidin-4-amine derivatives were synthesized by nucleophilic substitution of two chiral amines with 4-chloro-2-trifluoromethyl-6,7-dihydro-5H-cyclopenta[4,5]thieno[2,3-d]pyrimidine, which started from 2-amino-5,6-dihydro-4H-cyclopenta[b]thiophene-3-carbonitrile, trifluoroacetic acid (TFA) and phosphoryl trichloride via one-pot procedure [I → II; II + (R)/(S)-α-methylbenzylamine → (R)/(S)-III]. Their structures were determined by single-crystal X-ray diffraction. Enantiomer (R)-III, (R)-N-(1-phenylethyl)-2-trifluoromethyl-6,7-dihydro-5H-cyclopenta[4,5]thieno[2,3-d]pyrimidin-4-amine crystallizes in the tetragonal system, space group P4₃ with a = 8.6847(6), b = 8.6847(6), c = 22.419(2) Å, V = 1690.9(3) ų, Z = 4, D_c = 1.428 g/cm³, μ = 0.228 mm^-1, F(000) = 752, the final R = 0.0463 and wR = 0.1257 for 3442 observed reflections with I > 2(I). Enantiomer (S)-III, (S)-N-(1-phenylethyl)-2-trifluoromethyl-6,7-dihydro-5H-cyclopenta[4,5]thieno[2,3-d]pyrimidin-4-amine crystallizes in the tetragonal system, space group P41 with a = 8.688, b = 8.688, c = 22.421 Å, V = 1692.4 ų, Z = 4, Dc = 1.426 g/cm³, μ = 0.227 mm^-1, F(000) = 752, the final R = 0.0682 and wR = 0.1806 for 3182 observed reflections with I > 2(I). The preliminary bioassay indicated that the R-enantiomer exhibits higher antitumor activity against MCF-7 than gefitinib. In the experiment, the researchers used many compounds, for example, 2-Amino-5,6-dihydro-4H-cyclopenta[b]thiophene-3-carbonitrile (cas: 70291-62-2Recommanded Product: 2-Amino-5,6-dihydro-4H-cyclopenta[b]thiophene-3-carbonitrile).

2-Amino-5,6-dihydro-4H-cyclopenta[b]thiophene-3-carbonitrile (cas: 70291-62-2) 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.Recommanded Product: 2-Amino-5,6-dihydro-4H-cyclopenta[b]thiophene-3-carbonitrile

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts