Tag: 100-200

Structure-taste relationship of perillartine and nitro- and cyanoaniline derivatives was written by Iwamura, Hajime. And the article was included in Journal of Medicinal Chemistry in 1980.SDS of cas: 60979-25-1 This article mentions the following:

The relation between structure and taste potency of perillartine (I) and its analogs was investigated quant. by physicochem. parameters and regression anal. The results indicated that the hydrophobicity estimated from the octanol/water partition coefficient and the mol. widths from the bond axis connecting the oxime C atom and alicyclic ring are important, regardless of whether the taste is sweet or bitter, so far as taste potency is concerned. The structure-activity relation for the sweet/bitter ratio was not established quant., but the mol. width and thickness and the position-specific electronic effect appeared to delineate the ratio qual.; i.e., in principle, the wider and(or) the thicker the mol., the more bitter the taste. The quant. structure-activity relation of 5-nitro- and 5-cyanoaniline sweetener was formulated to show the nonsignificance of hydrophobicity within the compounds investigated but the importance of steric dimensions in determining the activity. In the experiment, the researchers used many compounds, for example, 3-Amino-4-methoxybenzonitrile (cas: 60979-25-1SDS of cas: 60979-25-1).

3-Amino-4-methoxybenzonitrile (cas: 60979-25-1) belongs to nitriles. Nitriles are polar, as indicated by high dipole moments. As liquids, they have high relative permittivities, often in the 30s. 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.SDS of cas: 60979-25-1

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Nitrile – Wikipedia,
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Cobalt(III) complex-promoted hydrolysis of phosphate diesters: comparison in reactivity of rigid cis-diaquo(tetraaza)cobalt(III) complexes was written by Chin, Jik;Banaszczyk, Mariusz;Jubian, Vrej;Zou, Xiang. And the article was included in Journal of the American Chemical Society in 1989.Name: 3,3′,3”-Nitrilotripropanenitrile This article mentions the following:

The efficiencies of three rigidly held cis-aquohydroxotetraazacobalt(III) complexes [(cyclen)Co(OH)(OH₂)]²⁺ (cyclen = 1,4,7,10-tetraazacyclododecane), [(tren)Co(OH)(OH₂)]²⁺ [tren = N(CH₂CH₂NH₂)₃], and [(trpn)Co(OH)(OH₂)]²⁺ [trpn = N(CH₂CH₂CH₂NH₂)₃] in promoting the hydrolysis of bis(p-nitrophenyl) phosphate (BNPP) have been compared. In neutral water at 50°, the rate constant for hydrolysis of the phosphate diester bond in [(cyclen)Co(OH)(BNPP)]⁺, [(tren)Co(OH)(BNPP)]⁺, [(trpn)Co(OH)(BNPP)]⁺ are 4.6 × 10^-1, 8.1 × 10^-3, and 2.5 s^-1, resp. [(Trpn)Co(OH)(BNPP)]⁺ is hydrolyzed at about the same rate as BNPP bound to a real enzyme from Enterobacter aerogenes and about 10¹⁰ times more rapidly than free BNPP. The dramatic increase in the activity of the Co(III) complex with change in the tetraamine ligand structure can be explained in terms of a detailed mechanism of the reaction. In the experiment, the researchers used many compounds, for example, 3,3′,3”-Nitrilotripropanenitrile (cas: 7528-78-1Name: 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. 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.Name: 3,3′,3”-Nitrilotripropanenitrile

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Nitrile – Wikipedia,
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Ethylene diamine grafted nanoporous UiO-66 as an efficient basic catalyst in the multi-component synthesis of 2-aminothiophenes was written by Erfaninia, N.;Tayebee, R.;Dusek, M.;Amini, M. M.. And the article was included in Applied Organometallic Chemistry in 2018.Application of 70291-62-2 This article mentions the following:

This study demonstrates ED-UiO-66 as a novel and effective solid nanoporous basic catalyst prepared through the amine grafting onto the pores of UiO-66. The manufactured nanoparticles were identified by FT-IR, XRD, TGA, FESEM, TEM, CHN and BET and the characterization results certified formation of a single phase nanoporous substance with the medium grain size less than 90 nm. The synthesized material was employed as an efficient catalyst for the preparation of 2-aminothiophenes I [R = 4,5-(-CH₂-)₅, 5-CH₃, 5-C₆H₅] through the Gewald method. This thermochem. stable nanocatalyst was environmentally safe, reusable and economic. Therefore, this methodol. can be simply extended for industrial goals. In the experiment, the researchers used many compounds, for example, 2-Amino-5,6-dihydro-4H-cyclopenta[b]thiophene-3-carbonitrile (cas: 70291-62-2Application of 70291-62-2).

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

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Nitrile – Wikipedia,
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Photocatalytic C-H Amination of Aromatics Overcoming Redox Potential Limitations was written by Morofuji, Tatsuya;Ikarashi, Gun;Kano, Naokazu. And the article was included in Organic Letters in 2020.Computed Properties of C8H8N2O This article mentions the following:

The photocatalytic C-H amination of aromatics overcoming redox potential limitations was reported. Radical cations of aromatic compounds were generated photocatalytically using Ru(phen)₃(PF₆)₂, which had a reduction potential at a high oxidation state (E_red(Ru^III/Ru^II) = +1.37 V vs SCE) lower than the oxidation potentials of aromatic substrates (E_ox = +1.65 to +2.27 V vs SCE). The radical cations were trapped with pyridine to give N-arylpyridinium ions, which were converted to aromatic amines. In the experiment, the researchers used many compounds, for example, 3-Amino-4-methoxybenzonitrile (cas: 60979-25-1Computed Properties of C8H8N2O).

3-Amino-4-methoxybenzonitrile (cas: 60979-25-1) belongs to nitriles. Nitrile carbon shifts are in the range of 115–125 ppm whereas in isonitriles the shifts are around 155–165 ppm. 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.Computed Properties of C8H8N2O

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Nitrile – Wikipedia,
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Synthesis, Characterization, Antimicrobial Activity Screening, and Molecular Docking Study of Pyrimidine Carbonitrile Derivatives was written by Bhat, Radhika;Begum, Noor Shahina. And the article was included in Russian Journal of Organic Chemistry in 2021.Computed Properties of C5H3ClN4 This article mentions the following:

The synthesis of pyrimidine carbonitrile derivatives I [R = 1-piperidyl, 2-phenylethylamino, 2-(1H-indol-3-ylmethylene)hydrazino, etc.] was described. The compounds I were characterized by FT-IR and ¹H and ¹³C- NMR spectroscopy and mass spectrometry. All the compounds I were evaluated for in-vitro antimicrobial activity against different bacterial and fungal strains. The min. inhibitory concentrations (MICs) of all the compounds I were validated. Compounds I [R = 2-[(3,4-dimethoxyphenyl)methylene]hydrazino, 1-piperidyl], which had the lowest MIC values were selected for cell leakage anal. and bacterial growth curve study. It was found that both the compounds I [R = 2-[(3,4-dimethoxyphenyl)methylene]hydrazino, 1-piperidyl] have potential to induce bacterial cell membrane rupture and disintegration. Field emission scanning electron microscopic anal. confirmed the effect of the selected compounds on the morphol. of both Gram-pos. (S. aureus) and Gram-neg. (E. coli) bacteria. The mechanism of interaction between the drug and the target protein of S. aureus and E. coli was studied by mol. docking. In the experiment, the researchers used many compounds, for example, 4-Amino-6-chloropyrimidine-5-carbonitrile (cas: 60025-09-4Computed Properties of C5H3ClN4).

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. Asymmetric bioreduction of nitriles is an attractive route to produce optically active nitriles as current metal-catalyzed hydrogenations tend to have low reactivity.Computed Properties of C5H3ClN4

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Nitrile – Wikipedia,
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Charge localization in the retro-Diels-Alder fragmentation of tetralins was written by Lightner, David A.;Steinberg, Frank S.. And the article was included in Organic Mass Spectrometry in 1970.SDS of cas: 29809-13-0 This article mentions the following:

The electron-impact induced retro-Diels-Alder reaction of 5- and 6-substituted tetralins has been examined Most electron-donating groups at C-5 retard the fragmentation relative to tetralin; whereas, electron-withdrawing groups slightly increase the fragmentation. In the experiment, the researchers used many compounds, for example, 5,6,7,8-Tetrahydronaphthalene-1-carbonitrile (cas: 29809-13-0SDS of cas: 29809-13-0).

5,6,7,8-Tetrahydronaphthalene-1-carbonitrile (cas: 29809-13-0) 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.SDS of cas: 29809-13-0

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Nitrile – Wikipedia,
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Action of stilbene on tetrachloro-ο-benzoquinone was written by Schonberg, Alexander;Latif, Nazih. And the article was included in Journal of the American Chemical Society in 1950.COA of Formula: C8H13N This article mentions the following:

Tetrachloro-ο-quinone (I) (1 g.) and (PhCH:)₂ (II) in 30 cc. C₆H₆, exposed 13 days to sunlight, give 2,3-diphenyl-5,6,7,8-tetrachloro-1,4-benzodioxan (III), m. about 172°; III results in 70% yield on boiling 1.2 g. I and 0.9 g. II in C₆H₆ 15 hrs. in the dark. I (0.6 g.) and 0.5 g. (p-MeC₆H₄CH:)₂, exposed 10 days to sunlight, give 2-phenyl-3-(p-tolyl)-5,6,7,8-tetrachloro-1,4-benzodioxan, m. 132°. III, heated 15 min. in a C₆H₄(CO₂Et)₂ bath (oil-pump vacuum), gives II. III does not react with ο-C₆H₄(NH₂)₂ (refluxed 2 hrs. in 90% AcOH). In the experiment, the researchers used many compounds, for example, 2-Cyclohexylacetonitrile (cas: 4435-14-7COA of Formula: C8H13N).

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.COA of Formula: C8H13N

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Synthesis of novel fused thienodiazaphosphorine derivatives from 2-amino-3-cyanothiophenes and Lawesson’s reagent was written by Khalladi, Khaoula;Touil, Soufiane. And the article was included in Journal of Sulfur Chemistry in 2012.Formula: C8H8N2S This article mentions the following:

In a simple one-pot procedure, treatment of 2-amino-3-cyanothiophenes with Lawesson’s reagent led to the new thieno[2,3-d][1,3,2]diazaphosphorine-6-thione-2-sulfides in good to excellent yields. A possible reaction mechanism, involving a Dimroth-type rearrangement, was proposed. The structure of obtained products was confirmed by NMR (¹H, ³¹P, and ¹³C) and IR spectroscopies and by mass spectrometry. In the experiment, the researchers used many compounds, for example, 2-Amino-5,6-dihydro-4H-cyclopenta[b]thiophene-3-carbonitrile (cas: 70291-62-2Formula: C8H8N2S).

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. Asymmetric bioreduction of nitriles is an attractive route to produce optically active nitriles as current metal-catalyzed hydrogenations tend to have low reactivity.Formula: C8H8N2S

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Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Organic catalysts. XL. Synthetic dehydrogenases. 8 was written by Mix, Hermann;Krause, Hans Walter. And the article was included in Chemische Berichte in 1956.Synthetic Route of C8H8N2 This article mentions the following:

Some isatins, CMe:CH.CH:CR.C:C.NH.CO.CO (I), and N-(7-methylisatin-4-carbonyl)amino acid Et esters (II), substituted in the 4-position, are prepared and tested for their dehydrogenase activity. Treating p-MeC₆H₄CO₂H with fuming HNO₃ yields 4,3-Me(O₂N)C₆H₃CO₂H, m. 188-9°, which, reduced with Raney Ni in dioxane at 120° and 100 atm., gives 90% 4,3-Me(H₂N)C₆H₃CO₂H (III), m. 162°. Heating 5 g. III in 150 cc. H₂O containing 2 cc. concentrated H₂SO₄ with 5.5 g. CCl₃CHO.H₂O (IV) and 6.5 g. (HONH₂)₂.H₂SO₄ (V) yields 3-isonitrosoacetamido-4-methylbenzoic acid which (10 g.), heated in 22 cc. concentrated H₂SO₄ at 85-90° and kept 0.5 hr. at 95-100°, gives 72% I (R = CO₂H) (VI), yellow-red needles, m. 278-80°; Et ester, prepared by heating 5 g. VI in 150 cc. EtOH-HCl 0.5 hr. on a water bath and chromatographing over Al₂O₃, orange rods, m. 205°. Heating 5 g. 4,3-Me(H₂N)C₆H₃CN, m. 81°, 6.3 g. IV, and 7.5 g. V in 430 cc. H₂O and 3 cc. concentrated H₂SO₄ gives 2-2.5 g. isonitroso compound which, heated with concentrated H₂SO₄, yields I (R = CONH₂), brick-red crystals, decompose above 270°. Adding 0.94 cc. ClCO₂Et dropwise to a solution of 2 g. VI and 2.28 g. Bu₃N in 20 cc. CHCl₃ at -5°, stirring the mixture 0.5 hr. at -5°, then adding 900 mg. PhNH₂, and stirring the mixture 12 hrs. give I (R = CONHPh), small red rods, m. 308°; I (R = CONEt₂), light red leaflets, m. 192°. The following II are prepared (amino acid given): alanine, light red rods, m. 254°; norvaline, light red leaflets, m. 220°; α-aminobutyric acid, red leaflets, m. 218-19°; glutamic di-Et ester, red needles, m. 171-2°; glutamic mono-Et ester, long red needles, m. 186-7°; phenylalanine, red needles, m. 225-6°; tryptophan Me ester, purple crystals, m. 254°. Treating 1.2 g. 2,4-Me₂C₆H₃NH₂ in 30 cc. H₂O and 1.16 g. concentrated H₂SO₄ with 1.7 g. IV and 1.9 g. V yields isonitrosoacetamido-p-xylene which, added to 10 cc. concentrated H₂SO₄ at 65-7° and the mixture heated 20 min. at 65-70°, gives 4,7-dimethylisatin, yellow-red precipitate, m. 261°. Reduction of 4,3-Me(O₂N)C₆H₃NHAc with Raney Ni at 120° and 100 atm. gives 100% 3,4-Me(H₂N)C₆H₃NHAc, m. 159°, which (6 g.), stirred 4-5 hrs. at 36-40° with 6 g. IV and 7.2 g. V, yields 3-isonitrosoacetamido-4-methylacetanilide. Heating the latter 45 min. in 10 cc. concentrated H₂SO₄ at 95-100° gives 4-amino-7-methylisatin, light red needles, charring above 310°. The dehydrogenase activity of these compounds has been tested by measuring the time required to decolorize a solution of 2 × 10^-5 moles methylene blue and 2.25 × 10^-4 moles DL-alanine in 71% HCONMe₂ at 40°. The results, given in a table, show that V is the most active catalyst. The introduction of the Me group at the 7-position has no effect on the dehydrogenation velocity. For the calculation of the partial velocities of the catalysis the P_S curves of some of the compounds are given. In the experiment, the researchers used many compounds, for example, 3-Amino-4-methylbenzonitrile (cas: 60710-80-7Synthetic Route of C8H8N2).

3-Amino-4-methylbenzonitrile (cas: 60710-80-7) 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.Synthetic Route of C8H8N2

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Amination of acrylonitrile in liquid ammonia was written by Murohashi, Susumu. And the article was included in Nagaoka Kogyo Tanki Daigaku Koto Semmon Gakko Kenkyu Kiyo in 1968.Name: 3,3′,3”-Nitrilotripropanenitrile This article mentions the following:

The title reaction was studied with or without a catalyst. Acrylonitrile (1 mole) was treated with liquid NH3 (>10 moles) in an autoclave at 100° for 30 min. in the presence of Raney Cu or Co to give mono(β-cyanoethyl)amine as the main product in 80% yield. Tris(β-cyanoethyl)amine was obtained when no catalyst or the Raney catalyst together with a polymerization inhibitor was used, while the bis- and tris(β-cyanoethyl)amines were produced in the presence of Raney Ni. After the amination, only the Co catalyst among Raney metal catalysts kept the ability as a hydrogenation catalyst. Successive amination and hydrogenation of acrylonitrile without isolation of the intermediate or further addition of the catalyst gave 1,3-propanediol in 80% yield. Gas chromatographic determination and life of the catalyst were also discussed. In the experiment, the researchers used many compounds, for example, 3,3′,3”-Nitrilotripropanenitrile (cas: 7528-78-1Name: 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. 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.Name: 3,3′,3”-Nitrilotripropanenitrile

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts