Month: January 2023

Ketimines. III. ω-Cyclohexylalkyl alkyl type was written by Pickard, P. L.;Young, C. W.. And the article was included in Journal of the American Chemical Society in 1951.Product Details of 4435-14-7 This article mentions the following:

In this abstract, R = cyclohexyl throughout.) Acid chlorides, R(CH₂)_XCl (read x, yield (%), b.p., d₄²³, n_D²⁰): 3, 92.5, b₁ 83°, 1.0175, 1.4710; 5, 96, b₁ 106°, 0.9987, 1.4714. Slow addition of the acid chlorides to NH₄OH at 0° and crystallization of the precipitate from MeOH-H₂O gave above 80% of the amides, R(CH₂)₃CONH₂: × = 3, m. 111°; 5, m. 117°. Dehydration with excess POCl₃ gave the nitriles, R(CH₂)_xCN (read x, yield (%), b.p., d₄²⁰, n_D²⁰): 1, 70, b₁ 57°. 0.9180, 1.4575; 2, 80, b₁ 71°, 0.9107, 1.4602; 3, 83, b₁ 82°, 0.9056, 1.4607; 4, 85, b₁ 93°, 0.8950, 1.4618; 5, 86, b₁ 112°, 0.9879, 1.4637. The ketimines, R(CH₂)_x C(:NH)CHMeEt were prepared from 0.25 mole MeEtCHBr and 0.20 mole nitrile by the method of Pickard and Vaughan (C.A. 45,381 1a) (read x, yield (%), b.p., d₄²⁰, and n_D²⁰): 2, 56, b₂ 101°, 0.8680, 1.4689; 3, 43, b₁ 107°, 0.8611, 1.4699; 4, 45, b₁ 121°, 0.8754, 1.4700; 5, 60, b₁ 130°, 0.8808, 1.4719. In the experiment, the researchers used many compounds, for example, 2-Cyclohexylacetonitrile (cas: 4435-14-7Product Details of 4435-14-7).

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. 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.Product Details of 4435-14-7

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Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Non-covalent thrombin inhibitors featuring P₃-heterocycles with P₁-monocyclic arginine surrogates was written by Reiner, John E.;Siev, Daniel V.;Araldi, Gian-Luca;Cui, Jingrong Jean;Ho, Jonathan Z.;Reddy, Komandla Malla;Mamedova, Lala;Vu, Phong H.;Lee, Kuen-Shan S.;Minami, Nathaniel K.;Gibson, Tony S.;Anderson, Susanne M.;Bradbury, Annette E.;Nolan, Thomas G.;Semple, J. Edward. And the article was included in Bioorganic & Medicinal Chemistry Letters in 2002.COA of Formula: C5H4N4 This article mentions the following:

Investigations on P₂-P₃-heterocyclic dipeptide surrogates directed towards identification of an orally bioavailable thrombin inhibitor led us to pursue novel classes of achiral, non-covalent P₁-arginine derivatives The design, synthesis, and biol. activity of inhibitors NC1-NC30 that feature three classes of monocyclic P₁-arginine surrogates will be disclosed: (1) (hetero)aromatic amidines, amines and hydroxyamidines, (2) 2-aminopyrazines, and (3) 2-aminopyrimidines and 2-aminotetrahydropyrimidines. In the experiment, the researchers used many compounds, for example, 2-Aminopyrimidine-5-carbonitrile (cas: 1753-48-6COA of Formula: C5H4N4).

2-Aminopyrimidine-5-carbonitrile (cas: 1753-48-6) 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. 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.COA of Formula: C5H4N4

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Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

β-Amino alcohols as ligands for asymmetric transfer hydrogenation of ketones in water was written by Wu, Xiaofeng;Li, Xiaohong;McConville, Matthew;Saidi, Ourida;Xiao, Jianliang. And the article was included in Journal of Molecular Catalysis A: Chemical in 2006.HPLC of Formula: 101219-69-6 This article mentions the following:

Chiral β-amino alcs. were used as ligands for ruthenium, rhodium and iridium-catalyzed asym. transfer hydrogenation of acetophenone derivatives in water with formate as reductant. The catalysts were shown to be capable of asym. transfer hydrogenation of ketones in water, but their activities and enantioselectivity varied with the ligands used and with solution pH values, with higher pH favoring higher rates and better enantioselectivity. 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. Asymmetric bioreduction of nitriles is an attractive route to produce optically active nitriles as current metal-catalyzed hydrogenations tend to have low reactivity.HPLC of Formula: 101219-69-6

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Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Cobalt(II)/TPPMS-Catalyzed Dehydrative Nucleophilic Substitution of Alcohols in Water was written by Hikawa, Hidemasa;Ijichi, Yukiko;Kikkawa, Shoko;Azumaya, Isao. And the article was included in European Journal of Organic Chemistry in 2017.Computed Properties of C8H5F3N2 This article mentions the following:

A green and sustainable direct dehydrative amination of alcs., catalyzed by cobalt(II)/TPPMS (sodium diphenylphosphinobenzene-3-sulfonate) in water, is described. Earth-abundant cobalt was used as Co(hfac)₂·xH₂O (hfac: hexafluoroacetylacetone), which acts as a highly efficient Lewis acidic catalyst. This simple atom-economical protocol features mild conditions without the need for a base or other additives and affords the corresponding benzylic and allylic anilines along with water as the only coproduct. Mechanistic studies suggest that this system is driven by direct nucleophilic substitution of alcs. In the experiment, the researchers used many compounds, for example, 2-Amino-4-(trifluoromethyl)benzonitrile (cas: 1483-54-1Computed Properties of C8H5F3N2).

2-Amino-4-(trifluoromethyl)benzonitrile (cas: 1483-54-1) 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. 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.Computed Properties of C8H5F3N2

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Nanochannel-based {BaZn}-organic framework for catalytic activity on the cycloaddition reaction of epoxides with CO₂ and deacetalization-Knoevenagel condensation was written by Lv, Hongxiao;Fan, Liming;Chen, Hongtai;Zhang, Xiutang;Gao, Yanpeng. And the article was included in Dalton Transactions in 2022.Application of 55490-87-4 This article mentions the following:

The rare combination of Ba(II) (5s) and Zn^II (3d) in the presence of the structure-oriented TDP⁶– ligand generated the nanochannel-based hybrid material {[(CH₃)₂NH₂]₂[BaZn(TDP)(H₂O)]·DMF·5H₂O}_n (NUC-51, H₆TDP = 2,4,6-tri(2,4-dicarboxyphenyl)pyridine), which possesses excellent physicochem. characteristics such as nanoscopic channels, high porosity, large sp. surface area and high heat/water-resistance. This is the first 3D [Ba^IIZn^II(CO₂)₆(H₂O)]-based nano-porous host framework, whose activated state NUC-51a possesses the coexistence of Lewis acid-base sites including 4-coordinated Zn²⁺ ions, 7-coordinated Ba²⁺ ions, uncoordinated carboxyl oxygen atoms and N_pyridine atoms. Catalytic experiments exhibited that activated NUC-51a possesses a high catalytic activity on the cycloaddition reactions of epoxides with CO₂ at 55°C, which can be ascribed to its structural advantages of nanoscale channels and rich bifunctional active sites. Moreover, NUC-51a could significantly accelerate the deacetalization-Knoevenagel condensation reaction in DMSO solvent at 70°C. In the experiment, the researchers used many compounds, for example, 2-(Anthracen-9-ylmethylene)malononitrile (cas: 55490-87-4Application of 55490-87-4).

2-(Anthracen-9-ylmethylene)malononitrile (cas: 55490-87-4) 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.Application of 55490-87-4

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

The reduction of α,β-unsaturated nitriles and α-halonitriles with sodium hydrogen telluride was written by Blay, Gonzalo;Cardona, Luz;Garcia, Begona;Lahoz, Luisa;Pedro, Jose R.. And the article was included in Tetrahedron in 1996.Safety of 2-Cyclohexylacetonitrile This article mentions the following:

Sodium hydrogen telluride reacts chemoselectively with α,β-unsaturated nitriles and α-halonitriles linked to aromatic and aliphatic substituents to give the corresponding saturated nitriles with good yields. In the experiment, the researchers used many compounds, for example, 2-Cyclohexylacetonitrile (cas: 4435-14-7Safety of 2-Cyclohexylacetonitrile).

2-Cyclohexylacetonitrile (cas: 4435-14-7) 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.Safety of 2-Cyclohexylacetonitrile

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Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Imidoyl chloride mediated one-pot synthesis of 3-electron withdrawing group substituted indoles was written by Zhan, Linjun;Hu, Wei;Wang, Mei;Huang, Bin;Long, Yaqiu. And the article was included in Huaxue Xuebao in 2021.SDS of cas: 67197-53-9 This article mentions the following:

Indole scaffold is widely present in pharmaceutical and pesticide products, dyes and natural products. The indole skeleton substituted by the electron withdrawing group at position 3 is an important class of bioactive indole derivatives Among them, 3-cyanoindole is a key module in the construction of privileged scaffold-based combinatory library and diversity-oriented synthesis for drug discovery. For these reasons, the design and synthesis of these scaffolds have received considerable attention in organic synthesis and have been extensively studied. However, the cyano group on the indole was introduced directly in previously reported methods. Due to the high toxicity of cyanide, the application of these reactions is limited. Imidoyl chloride, a highly reactive synthon, which was successfully used as a module for the construction of quinolones, quinazolines, benzimidazoles and other drug-like privileged scaffolds by our group. By making use of the imidoyl chloride as the active intermediate to mediate a cascade reaction to form the heterocycle, we developed a new one-pot synthesis to construct the 3-cyano or carboxylate-indole derivatives The reaction proceeded via two sequential steps: initial formation of imidoyl chloride starting from N-substituted arylamide and thionyl chloride, followed by 2-bromo-arylnitrile carbanion nucleophilic addition, elimination and Ulmann reaction. This synthetic methodol. is featured with cheap and readily available starting materials, high reaction yields, high functional group tolerance and broad substrate scope. This reaction is a direct synthesis not requiring prefunctionalization, and highly atom- and step-economic. It’s worth noting that it’s the first time building 3-cyanoindole scaffold commenced with the substrates bearing cyano group, which is of great importance for avoiding potential safety hazards. In the experiment, the researchers used many compounds, for example, 2-(2,6-Dibromophenyl)acetonitrile (cas: 67197-53-9SDS of cas: 67197-53-9).

2-(2,6-Dibromophenyl)acetonitrile (cas: 67197-53-9) 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.SDS of cas: 67197-53-9

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Solvent-free synthesis of 2-aminothiophene-3-carbonitrile derivatives using high-speed vibration milling was written by Xu, Fang;Li, Yujin;Xu, Fengshuang;Ye, Qing;Han, Liang;Gao, Jianrong;Yu, Wubin. And the article was included in Journal of Chemical Research in 2014.Quality Control of 2-Amino-5,6-dihydro-4H-cyclopenta[b]thiophene-3-carbonitrile This article mentions the following:

Solvent-free synthesis of 2-aminothiophene-3-carbonitrile derivatives e.g., I via one-pot cyclo-condensation of various ketones, malononitrile with elemental sulfur employing high-speed vibration milling with diethylamine as the catalyst was developed. The main advantages of this method are short reaction times, facile conditions, good yields, use of inexpensive catalyst and environmental friendly conditions. 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. 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. Quality Control of 2-Amino-5,6-dihydro-4H-cyclopenta[b]thiophene-3-carbonitrile

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Discovery of a Potent and Selective PI3Kδ Inhibitor (S)-2,4-Diamino-6-((1-(7-fluoro-1-(4-fluorophenyl)-4-oxo-3-phenyl-4H-quinolizin-2-yl)ethyl)amino)pyrimidine-5-carbonitrile with Improved Pharmacokinetic Profile and Superior Efficacy in Hematological Cancer Models was written by Shukla, Manojkumar R.;Patra, Sukanya;Verma, Mahip;Sadasivam, Gayathri;Jana, Nirmal;Mahangare, Sachin J.;Vidhate, Prashant;Lagad, Dipak;Tarage, Anand;Cheemala, Murthy;Kulkarni, Chaitanya;Bhagwat, Shankar;Chaudhari, Vinod D.;Sayyed, Majid;Pachpute, Vipul;Phadtare, Ramesh;Gole, Gopal;Phukan, Samiron;Sunkara, Brahmam;Samant, Charudatt;Shingare, Manisha;Naik, Aditya;Trivedi, Sneha;Marisetti, Ajit Kumar;Reddy, Madhusudhan;Gholve, Milind;Mahajan, Nilesh;Sabde, Sudeep;Patil, Vinod;Modi, Dipak;Mehta, Maneesh;Nigade, Prashant;Tamane, Kaustubh;Tota, Swati;Goyal, Hemant;Volam, Harish;Pawar, Shashikant;Ahirrao, Prajakta;Dinchhana, Lal;Mallurwar, Sadanand;Akarte, Atul;Bokare, Anand;Kanhere, Rupesh;Reddy, Neetinkumar;Koul, Sarita;Dandekar, Manoj;Singh, Minakshi;Bernstein, Peter R.;Narasimham, Lakshmi;Bhonde, Mandar;Gundu, Jayasagar;Goel, Rajan;Kulkarni, Sanjeev;Sharma, Sharad;Kamboj, Rajender Kumar;Palle, Venkata P.. And the article was included in Journal of Medicinal Chemistry in 2020.Application of 60025-09-4 This article mentions the following:

PI3Kδ inhibitors have been approved for B-cell malignancies like CLL, small lymphocytic lymphoma, and so forth. However, currently available PI3Kδ inhibitors are nonoptimal, showing weakness against at least one of the several important properties: potency, isoform selectivity, and/or pharmacokinetic profile. To come up with a PI3Kδ inhibitor that overcomes all these deficiencies, a pharmacophoric expansion strategy was employed. Herein, we describe a systematic transformation of a “three-blade propeller” shaped lead, 2,3-disubstituted quinolizinone 11, through a 1,2-disubstituted quinolizinone 20 to a novel “four-blade propeller” shaped 1,2,3-trisubstituted quinolizinone 34. Compound 34 (I)has excellent potency, isoform selectivity, metabolic stability across species, and exhibited a favorable pharmacokinetic profile. Compound 34 also demonstrated a differentiated efficacy profile in human germinal center B and activated B cell-DLBCL cell lines and xenograft models. Compound 34 qualifies for further evaluation as a candidate for monotherapy or in combination with other targeted agents in DLBCLs and other forms of iNHL. In the experiment, the researchers used many compounds, for example, 4-Amino-6-chloropyrimidine-5-carbonitrile (cas: 60025-09-4Application of 60025-09-4).

4-Amino-6-chloropyrimidine-5-carbonitrile (cas: 60025-09-4) 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. 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 60025-09-4

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Electrophoretic migration imaging process was written by VanAllan, J. A.;Rossi, L. J.;Bloom, M. S.;Regan, M. T.;Wright, H. E.;Kaukeinen, J. Y.. And the article was included in Research Disclosure in 1978.Product Details of 55490-87-4 This article mentions the following:

Twenty-five photosensitive compounds having the general structure Z(CH:CRR¹)_n where Z is phenylene, naphthylene, anthracenyl, anthracenediyl, or dibenzothiendiyl, n = 1 or 2, and R and R¹ are H, CN, alkylsulfonyl, alkylcarbonyl, arylcarbamoyl, cyanoaryl, arylcarbonyl, or together form an substituted or unsubstituted ring are described for use in electrophoretic imaging. Thus, a dispersion (containing Isopar G 2.2, Solvesso 100 1.3, Piccotex 100 1.4, and lauryl methacrylate-Li methacrylate-methacrylic acid-vinyltoluene polymer 0.1 g) 5 and 5,5′-(9,10-anthracenediyldimethylidyne)bis[3,4-di(p-nitrophenyl)furan-2-one] 0.045 g were milled with stainless steel balls 12 g for 3 h and then evaluated to show a useful level of photosensitivity. In the experiment, the researchers used many compounds, for example, 2-(Anthracen-9-ylmethylene)malononitrile (cas: 55490-87-4Product Details of 55490-87-4).

2-(Anthracen-9-ylmethylene)malononitrile (cas: 55490-87-4) belongs to nitriles. Trimerization of aromatic nitriles requires harsh reaction conditions, high temperatures, long reaction times, and pressure. In addition, Nitriles can react with alkynes, which leads to an increase in carbon chain length (carbocyanation).Product Details of 55490-87-4

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts