Month: January 2023

Tris(2-cyanoethyl)amine was written by Xu, An-Wu;Cai, Yue-Peng;Su, Cheng-Yong;Liu, Hong-Ke. And the article was included in Acta Crystallographica, Section C: Crystal Structure Communications in 2000.COA of Formula: C9H12N4 This article mentions the following:

In the title compound, N(CH₂CH₂CN)₃, (I), the three cyanoethyl groups adopt a conformation with the CN groups (I) oriented in the same direction, suggesting the compound may behave as a potential tripodal ligand. Crystallog. data are given. In the experiment, the researchers used many compounds, for example, 3,3′,3”-Nitrilotripropanenitrile (cas: 7528-78-1COA of Formula: C9H12N4).

3,3′,3”-Nitrilotripropanenitrile (cas: 7528-78-1) 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.COA of Formula: C9H12N4

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

SAR study of 5-alkynyl substituted quinazolin-4(3H)-ones as phosphoinositide 3-kinase delta (PI3Kδ) inhibitors was written by Wei, Manman;Zhang, Xi;Wang, Xiang;Song, Zilan;Ding, Jian;Meng, Ling-Hua;Zhang, Ao. And the article was included in European Journal of Medicinal Chemistry in 2017.Electric Literature of C5H3ClN4 This article mentions the following:

PI3Kδ is a key component in the aberrant signaling transduction in B cell malignancy, therefore specific targeting PI3Kδ has become an attractive molecularly targeted therapy for chronic lymphocytic leukemia (CLL). Herein, we describe the discovery and optimization of a series of 5-alkynyl substituted PI3Kδ inhibitors based on the first FDA-approved inhibitor idelalisib. Compound 8d bearing the 1-morpholinohex-5-yn-1-one moiety as the C5-substituent was identified to have high potency against PI3Kδ (3.82 nM) and SU-DHL-6 cells (7.60 nM), resp. It was 154-fold selective over PI3Kα, 133-fold selective against PI3Kβ, and 24-fold selective against PI3Kγ. Treatment of MOLT-4 and SU-DHL-6 cells with compound 8d for 1 h resulted in reduction of phosphorylation of both Akt (S473) and its downstream S6k1 (T389) in a concentration-dependent manner. Compound 8d showed potent anti-proliferative activity as well against T lymphoblast MOLT-4, suggesting its potential activity in T-cell leukemia. In the experiment, the researchers used many compounds, for example, 4-Amino-6-chloropyrimidine-5-carbonitrile (cas: 60025-09-4Electric Literature of C5H3ClN4).

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. 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. Electric Literature of C5H3ClN4

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Ketene gem-dithiols; a convenient one-step procedure from aliphatic active methylenes: reactions and synthesis of polyfunctionally substituted thia- and azaheteroaromatics was written by Zayed, Salem E.. And the article was included in Phosphorus, Sulfur and Silicon and the Related Elements in 1996.Application of 58168-20-0 This article mentions the following:

It has been reported in the current literature that the isolation of certain ketene gem dithiols has failed due to dimerization. Generation of ketene gem-dithiols via trapping with other reactants led to formation of pyridine, pyrrole, pyridothiadiazole and pyrazolone derivatives In the experiment, the researchers used many compounds, for example, Ethyl 5-amino-4-cyano-3-(2-ethoxy-2-oxoethyl)thiophene-2-carboxylate (cas: 58168-20-0Application of 58168-20-0).

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

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Nitriles in heterocyclic synthesis: novel routes to cyclopentenothienopyridines, cyclopentenothienopyrimidenes and cyclopentenopyrrolopyrazoles was written by Harb, Abdel Fattah Ali. And the article was included in Egyptian Journal of Pharmaceutical Sciences in 1992.Safety of 2-Amino-5,6-dihydro-4H-cyclopenta[b]thiophene-3-carbonitrile This article mentions the following:

Aminocyclopentenothiophenecarbonitrile I prepared via an extension to the Gewald reaction, was converted into the cyclopentenothienopyridines II (R = H, NH₂) and III by treatment with acrylonitrile, malononitrile and Et cyanoacetate. I was converted into the corresponding cyclopentenothienopyrimidines IV (X = S, R¹ = NHPh; X = O, R¹ = Me, H) on treatment with Ph isothiocyanate, acetic anhydride and triethylorthoformate resp. Also the corresponding cyclopentenopyrrolopyrazole V was obtained by treating I with hydrazine hydrate. In the experiment, the researchers used many compounds, for example, 2-Amino-5,6-dihydro-4H-cyclopenta[b]thiophene-3-carbonitrile (cas: 70291-62-2Safety of 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. Trimerization of aromatic nitriles requires harsh reaction conditions, high temperatures, long reaction times, and pressure. 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. Safety of 2-Amino-5,6-dihydro-4H-cyclopenta[b]thiophene-3-carbonitrile

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Rh^III– and Ir^III-catalyzed asymmetric transfer hydrogenation of ketones in water was written by Wu, Xiaofeng;Li, Xiaohong;Zanotti-Gerosa, Antonio;Pettman, Allan;Liu, Jianke;Mills, Allan James;Xiao, Jianliang. And the article was included in Chemistry – A European Journal in 2008.Recommanded Product: (R)-4-(1-Hydroxyethyl)benzonitrile This article mentions the following:

Asym. transfer hydrogenation (ATH) of ketones by formate in neat water is shown to be viable with Rh-TsDPEN and Ir-TsDPEN catalysts, derived in situ from [Cp^*MCl₂]₂ (M = Rh, Ir) and TsDPEN. A variety of ketones were reduced, including non-functionalized aryl ketones, heteroaryl ketones, keto esters, and unsaturated ketones. In comparison with Ir-TsDPEN and the related Ru^II catalyst, the Rh^III catalyst is most efficient in water, affording enantioselectivities of up to 99% ee at substrate/catalyst (S/C) ratios of 100-1000 even without working under an inert atm. The aqueous phase reduction is shown to be highly pH-dependent; the optimum pH windows for TOF greater than 50 molmol^-1h^-1 for Rh- and Ir-TsDPEN are 5.5-10.0 and 6.5-8.5, resp. Outside the pH window, the reduction becomes slow or stagnant depending on the pH. However, the enantioselectivities erode only under acidic conditions. At a higher S/C ratio, the aqueous ATH by Rh-TsDPEN is shown to be product – as well as byproduct – inhibited; the product inhibition appears to stem at least partly from the reaction being reversible. The aqueous phase reduction is simple, efficient and environmentally benign, thus presenting a viable alternative for asym. reduction In the experiment, the researchers used many compounds, for example, (R)-4-(1-Hydroxyethyl)benzonitrile (cas: 101219-69-6Recommanded Product: (R)-4-(1-Hydroxyethyl)benzonitrile).

(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. 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: (R)-4-(1-Hydroxyethyl)benzonitrile

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Immobilization of rhodium-based transfer hydrogenation catalysts on mesoporous silica materials was written by Long, Jie;Liu, Guohua;Cheng, Tanyu;Yao, Hui;Qian, Qingqian;Zhuang, Jinglan;Gao, Fei;Li, Hexing. And the article was included in Journal of Catalysis in 2013.Synthetic Route of C9H9NO This article mentions the following:

Rhodium TsDPEN complex was immobilized on mesoporous silica as reusable catalyst for transfer hydrogenation of aryl ketones into chiral benzyl alcs. The immobilization procedure comprised in situ reaction of [Cp^*RhCl₂]₂ with (S,S)-(MeO)₃SiCH₂CH₂C₆H₄SO₂NHCHPhCHPhNH₂ (1) followed by hydrolytic chemisorption on mesoporous silica, or cocondensation of (EtO)₄Si with 1 followed by reaction of functionalized silica with [Cp^*RhCl₂]₂. A series of chiral heterogeneous rhodium catalysts obtained via immobilization of chiral N-sulfonylated diamine-based organorhodium complexes within mesoporous silicate networks have been obtained through the postgrafting, postmodification, and co-condensation strategies. Structural analyses and characterizations disclose their well-defined single-site rhodium species within materials, while electron microscopy images reveal their highly ordered dimensional-hexagonal mesostructures. By systemically comparing these prepared strategies, it is found that they exhibit obviously different catalytic activities and enantioselectivities in aqueous asym. transfer hydrogenation of aromatic ketones. The direct anchoring of chiral organorhodium complexes onto the outside surface of mesoporous silica can maintain high enantioselectivity, while the co-condensation of chiral organorhodium complexes into the inside surface of mesoporous silica can form a uniform distribution of active rhodium centers. Both strategies show higher catalytic efficiency than the postmodification strategy in enantioselective performance. This outcome from the study clearly demonstrates the nature of these heterogeneous catalysts based on different immobilization strategies and offers a general way to optimize the prepared strategy to adjust the catalytic efficiency of heterogeneous catalysts. 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. 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. 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 C9H9NO

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Quantitative structure-activity relationship studies on relative sweetness of aniline derivatives was written by Zhu, Lilan. And the article was included in Shipin Kexue (Beijing, China) in 2011.Category: nitriles-buliding-blocks This article mentions the following:

In this article, a novel connectivity index (^mL_t^v) was established by extending Kier’s connectivity index (^mX_t^v). The quant. structure-activity relationship (QSSR) between the relative sweetness (R_S/B) of 20 nitroaniline and cyanoaniline derivatives and ^mL_t^v was explored using multivariate statistical regression. Based on leaps-and-bounds regression anal., an optimal binary QSAR model was set up. The traditional correlation coefficient (R) and cross-validation correlation coefficient (Q²) of leave-one-out (LOO) were 0.943 and 0.844, resp. These results demonstrated that the model was highly reliable and had good prediction capability. Meanwhile, it was better than that of Kier’s connectivity index. Moreover, the model could be explained by the AH-B-W sweetness theory of Shallenberger and Kier. In the experiment, the researchers used many compounds, for example, 3-Amino-4-methoxybenzonitrile (cas: 60979-25-1Category: nitriles-buliding-blocks).

3-Amino-4-methoxybenzonitrile (cas: 60979-25-1) 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).Category: nitriles-buliding-blocks

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Polynitrile- and polyamine-functionalized poly(trimethylenimine) dendrimers was written by Woerner, Christof;Muelhaupt, Rolf. And the article was included in Angewandte Chemie in 1993.Recommanded Product: 3,3′,3”-Nitrilotripropanenitrile This article mentions the following:

Sequential acrylonitrile-condensation and Raney nickel-catalyzed hydrogenation of poly(trimethylenimine) N[CH₂CH₂CH₂N(CH₂CH₂NH₂)₂]₃ gave poly(trimethylenimine) I (X = CN). This sequence was repeated two more times to give a dendrimer complex, which was analyzed spectroscopically. 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. 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.Recommanded Product: 3,3′,3”-Nitrilotripropanenitrile

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Bovine serum albumin-catalyzed one-pot synthesis of 2-aminothiophenes via Gewald reaction was written by Zhao, Dan-Dan;Li, Li;Xu, Fan;Wu, Qi;Lin, Xian-Fu. And the article was included in Journal of Molecular Catalysis B: Enzymatic in 2013.Quality Control of 2-Amino-5,6-dihydro-4H-cyclopenta[b]thiophene-3-carbonitrile This article mentions the following:

A novel bovine serum albumin (BSA)-catalyzed Gewald reaction in one-pot was developed in this work. The influence of reaction conditions including solvent, temperature and catalyst loading was investigated, and 12 multi-substituted 2-aminothiophene derivatives were prepared with moderate to excellent yields. Recycle experiments were designed to demonstrate the reusability of BSA. This novel activity of BSA to catalyze Gewald reaction is of practical significance in expanding the application of biocatalysts. In the experiment, the researchers used many compounds, for example, 2-Amino-5,6-dihydro-4H-cyclopenta[b]thiophene-3-carbonitrile (cas: 70291-62-2Quality Control of 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. 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.Quality Control of 2-Amino-5,6-dihydro-4H-cyclopenta[b]thiophene-3-carbonitrile

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Contribution to Our Knowledge of the Terpenes and the Ethereal Oils. Eighty-fourth Paper. Carboxylic Acids of Cyclic Hydrocarbons and Their Transformation Products was written by Wallach, O.. And the article was included in Justus Liebigs Annalen der Chemie in 1907.Name: 2-Cyclohexylacetonitrile This article mentions the following:

Acids and bases containing the characteristic groups in the side chain were studied. 1. Cyclohexanone derivatives. Two isomeric acids, (I) and (II) were formed on dehydrating cyclohexanolacetic acid. Δ^2.7-Cyclohexeneacetic acid (II), m. 91°, was prepared as already described (Ibid., 347, 329) added HBr to form a compound, m. 89-90°, C₈H₁₃BrO₂, and Br₂ to form C₄H₁₂Br₂O₂ m. 133-34°. Oxidized with permanganate, cyclohexanone was formed. The isomeric acid, m. 38°, probably structure I, yielded the same compound as the Δ^1.7-acid and the hexanolacetic acid with halogen hydrides. Monochlorcyclohexylacetic acid, m. 83°. Monobromcyclohexylacetic acid, m. 89-90°. Monoiodocyclohexylacetic acid, m. 99-100°. The acid, m. 38°, added two atoms bromine to form a compound, m. 119-20°, and distilled with sulphuric acid yielded a lactone. The acid chloride and the amide, m. 152-53°, were prepared. On oxidation, no definite products could be identified. Cyclohexylacetic acid, b. 245-47°, m. 30-31°, was prepared by reduction (Zn dust and acetic acid) of the brom- or iodo- acid. Amide, m. 168°. Nitrile, b. 215-17°, on reduction yielded, β-cyclohexylethylamine, b. 188-189°. Hydrochloride, m. 252-53°; chlorplatinate, m. 253-54°; ureide, m. 85-86°; methylammonium iodide, m. 221-22°. Cyclohexylmethylamine, b. 162-164°, was prepared from the amide, bromine and alkali. Hydrochloride, m. above 210°. Chlorplatinate, m. 240° (decompose). Ureide, m. 170-72°. Cyclohexylacetic acid distilled with lime yielded the completely hydrated dibenzylketone. Semicarbazone, m. 142-45°. Similarly cyclohexylacetone, b. 198-200°, was prepared. Semicarbazone, m. 165-66°. II Suberone derivatives. The methods used were the same as before. Suberylacetic acid, (cycloheptylacetic acid), b₁₀ 165°. Silver salt. Amide, m. 146-48°. Amine, b. 193-95°, [n]_D=1.4719, hydrochloride, m. 229-32°; chlorplatinate; ureide, m. 127-29°; trimethylammonium iodide, m. 223°. III Cyclopentanone derivatives. Cyclopentylacetic acid, b. 226-30°. Amide, m. 143-45°. Amine, b. 139-45°; hydrocldoride, chlorplatinate. Cyctopentanone and ethyl α-isobrombutyrate condensed with zinc formed pentanolisobutyric ester, b₁₁ 108-13°, which lost water on heating with potassium acid sulphate and yielded cyclopenteneisobutyric acid, b₁₁ 148-50°. Silver salt. HCl was added readily to form monochlorcyclopentylisobutyric acid, m. 122.5-123.5°. Monobromcyclopentylisobutyric acid, m. 113-14°. Moniodocyclopentylisobutyric acid, m. 107-108°. The dry distillation of the pentene isobutyric acid yielded a hydrocarbon, C₁₄H₈, b. 136-37° probably chiefly, since on oxidation cyclopentanone (semicarbazone) was formed. An isomer, was also formed and could also be obtained from the first on prolonged heating with alcoholic sulphuric acid. IV 1,4-Methylcyclohexonone derivatives. (Edgar Evans). 1,4-Methylhexeneacetic acid, (Ibid., 343, 345) CH₃C_6?H₉:CH.CO₂H, m. 42-43°. Monochlorcyclomethylhexylacetic acid, m. 88-89°. Monobromcyclomethylhexylacetic acid, m. 85-86°. Dibromcyclomethylhexylacetic acid, m. 97-99°. Cyclomethylhexeneacetomide, m. 155-56°. Nitrile, b₁₅ 107°, 1,4-Cyclomethylhexylacetic acid, m. 63-65°. Amide, m. 161-62°. V Menthone derivatives (Eduard Schellack). Menthone condensed with methylbromacetate and zinc yielded mentholacetic acid methyl ester, , m. 32-33°, b_.10 136-137°. Acid, m. 82-83°, b₁₁ 193-197°. Brommenthylacetic acid. In the preparation of mentheneacetic acid, a lactone, C₁₂H₂₀O₂, b. 300-305°, [n]_D=1.4781 at 22°, was obtained, which, on boiling with HI and phosphorus yielded a substance, m. 88.5-89.5°, isomeric with the lactone. The liquid lactone was levorotatory, the solid, dextrorotatory. Brommenthylacetic acid reduced gave menthylacetic acid, b₁₁ 166-170°. Amide, m. 148-150°. 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. 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.Name: 2-Cyclohexylacetonitrile

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts