Month: December 2022

Fang, Zengjun published the artcileSynthesis and Biological Evaluation of a Series of 2-((1-substituted-1H-1,2,3-triazol-4-yl)methylthio)-6-(naphthalen-1-ylmethyl)pyrimidin-4(3H)-one As Potential HIV-1 Inhibitors, Computed Properties of 612-13-5, the publication is Chemical Biology & Drug Design (2015), 86(4), 614-618, database is CAplus and MEDLINE.

A series of (arylmethyl)(arylmethyltriazolylmethylthio)dihydropyrimidinones I (R = 1-naphthalenyl, 2,6-dichlorophenyl; R¹ = H, I, Me; R² = Ph, 4-FC₆H₄, 4-MeOC₆H₄, 4-H₂NCOC₆H₄, 2-NCC₆H₄, 2-MeC₆H₄, 4-H₂NSO₂C₆H₄) were synthesized using copper-catalyzed azide-alkyne cycloadditions and evaluated as inhibitors of HIV-1. Among them, the most active HIV-1 inhibitor was compound I (R = 2,6-dichlorophenyl; R¹ = Me; R² = 4-H₂NSO₂C₆H₄), which exhibited similar HIV-1 inhibitory potency (EC₅₀ = 3.22 U+03BCM) compared with 3TC (EC₅₀ = 2.24 U+03BCM). None of these compounds demonstrated inhibition against HIV-2 replication. The preliminary structure-activity relationship (SAR) of these new derivatives was discussed briefly.

Chemical Biology & Drug Design published new progress about 612-13-5. 612-13-5 belongs to nitriles-buliding-blocks, auxiliary class Organic Pigment, name is 2-(Chloromethyl)benzonitrile, and the molecular formula is C8H6ClN, Computed Properties of 612-13-5.

Referemce:
https://en.wikipedia.org/wiki/Nitrile,
Nitriles – Chemistry LibreTexts

Ozawa, Jun published the artcileSilver-Catalyzed C(sp³)-H Chlorination, Name: 2-(Chloromethyl)benzonitrile, the publication is Organic Letters (2017), 19(6), 1430-1433, database is CAplus and MEDLINE.

A silver-catalyzed chlorination of benzylic, tertiary, and secondary C(sp³)-H bonds was developed. The reaction proceeded with as low as 0.2 mol % catalyst loading at room temperature under air atm. with synthetically useful functional group compatibility. The regioselectivity and reactivity tendencies suggest that the chlorination proceeded through a radical pathway, but an intermediate alkylsilver species cannot be ruled out.

Organic Letters published new progress about 612-13-5. 612-13-5 belongs to nitriles-buliding-blocks, auxiliary class Organic Pigment, name is 2-(Chloromethyl)benzonitrile, and the molecular formula is C8H6ClN, Name: 2-(Chloromethyl)benzonitrile.

Referemce:
https://en.wikipedia.org/wiki/Nitrile,
Nitriles – Chemistry LibreTexts

Wendt, Ola F. published the artcileAcetonitrile and propionitrile exchange at palladium(II) and platinum(II), COA of Formula: C10H12F6N4O6PdS2, the publication is Journal of the Chemical Society, Dalton Transactions: Inorganic Chemistry (1997), 4733-4738, database is CAplus.

Ligand exchange at square-planar [Pd(MeCN)₄]²⁺ and [Pd(EtCN)₄]²⁺ has been studied by ¹H NMR line broadening and at [Pt(MeCN)₄]²⁺ and [Pt(EtCN)₄]²⁺ by isotopic labeling using ¹H NMR spectroscopy in deuterated nitromethane. Exchange takes place via two-term rate laws R_ex/4 = (k₁ + k₂[RCN])c_M with well defined k₁ paths. Rate constants per co-ordination site k₁²⁹⁸/s^-1, k₂²⁹⁸/kg mol^-1 s^-1 are 6.9 ± 1.6, 34 ± 3; 0.59 ± 0.12, 34 ± 3; 10.7 ± 1.8, 35 ± 4; (5.1 ± 2.3) × 10^-6, (2.8 ± 0.2) × 10^-5 and (5.5 ± 1.0) × 10^-6, (3.3 ± 0.2) × 10^-5 for [Pd(MeCN)₄][CF₃SO₃]₂, [Pd(MeCN)₄][BF₄]₂, [Pd(EtCN)₄][CF₃SO₃]₂, [Pt(MeCN)₄][CF₃SO₃]₂ and [Pt(EtCN)₄][CF₃SO₃]₂, resp. For [Pd(MeCN)₄]²⁺ the k₁ path is much larger for triflate than for tetrafluoroborate as counter ion. Changing the tetrafluoroborate concentration has no effect on the exchange rate of acetonitrile at [Pd(MeCN)₄]²⁺. In this case the k₁ path is ascribed to an attack by solvent at the metal center. For triflate saturation kinetics is observed This can be rationalized in terms of ion-pair formation followed by reversible intramol. exchange of nitrile for triflate within the ion pair, with an equilibrium constant K_ip³⁰⁰ = 8 ± 2 kg mol-¹ and a rate constant k³⁰⁰ = 12.5 ± 1.3 s^-1. All activation entropies are neg., indicating associative activation. A new, simple one-step synthesis of the substrate complexes as their triflate salts, using [M(acac)₂] (acac = acetylacetonate) as starting material, and of [Pd(MeCN)₄][BF₄]₂ using palladium(II) acetate, is described.

Journal of the Chemical Society, Dalton Transactions: Inorganic Chemistry published new progress about 68569-14-2. 68569-14-2 belongs to nitriles-buliding-blocks, auxiliary class Palladium, name is Tetrakis(acetonitrile)palladium(II) Ditriflate, and the molecular formula is C25H29N9O3, COA of Formula: C10H12F6N4O6PdS2.

Referemce:
https://en.wikipedia.org/wiki/Nitrile,
Nitriles – Chemistry LibreTexts

Jagadeesh, Rajenahally V. published the artcile‘Nanorust’-catalyzed Benign Oxidation of Amines for Selective Synthesis of Nitriles, Related Products of nitriles-buliding-blocks, the publication is ChemSusChem (2015), 8(1), 92-96, database is CAplus and MEDLINE.

The selective and environmentally benign oxidative conversion of primary amines for the synthesis of structurally diverse aromatic, aliphatic and heterocyclic nitriles using a reusable ‘nanorust’ (nanoscale Fe₂O₃)-based catalysts applying mol. oxygen is reported.

ChemSusChem published new progress about 261951-87-5. 261951-87-5 belongs to nitriles-buliding-blocks, auxiliary class Trifluoromethyl,Fluoride,Nitrile,Benzene,Ether, name is 4-Methoxy-3-(trifluoromethyl)benzonitrile, and the molecular formula is C9H6F3NO, Related Products of nitriles-buliding-blocks.

Referemce:
https://en.wikipedia.org/wiki/Nitrile,
Nitriles – Chemistry LibreTexts

Tiburcio, Jorge published the artcileConformational Behavior and Coordination Chemistry of 2,11-Dithia[3.3]orthocyclophane with Platinum Group Metals, Synthetic Route of 68569-14-2, the publication is Inorganic Chemistry (2002), 41(14), 3779-3785, database is CAplus and MEDLINE.

The compound 2,11-dithia[3.3]orthocyclophane (L) is a mesocyclic dithioether that can act as a bidentate ligand in different conformations. In the ionic heteroleptic complexes [PtL(η⁴-cod)][CF₃SO₃]₂ (1), [RhL(η⁴-cod)][CF₃SO₃] (2), and [IrL(η⁴-cod)][CF₃SO₃] (3) (cod = 1,5-cyclooctadiene), L is coordinated in the anti I conformation both in solution and in the solid state, as revealed by an x-ray diffraction study of complex 1. However, in [PdL(PPh₃)₂][SO₃CF₃]₂ (4) and [PtL(PPh₃)₂][SO₃CF₃]₂ (5), L exhibits two different conformations:anti I and anti II in a 40:60 ratio, as observed by ¹H and ³¹P NMR spectroscopy, with no exchange up to 90°. The homoleptic complexes [PdL₂][SO₃CF₃]₂ (6) and [PtL₂][SO₃CF₃]₂ (7), with two ligands bound to the metal, display two isomers in solution, one of them with L in conformations anti I-anti II and the other with conformations anti II-anti II with a 75:25 ratio. The x-ray structure of 6 showed only the presence of the anti II-anti II isomer in the solid state. All complexes were synthesized by the reaction of a suitable chloride complex with 2 equiv of Ag triflate and 1 equiv of L.

Inorganic Chemistry published new progress about 68569-14-2. 68569-14-2 belongs to nitriles-buliding-blocks, auxiliary class Palladium, name is Tetrakis(acetonitrile)palladium(II) Ditriflate, and the molecular formula is C23H43NP2, Synthetic Route of 68569-14-2.

Referemce:
https://en.wikipedia.org/wiki/Nitrile,
Nitriles – Chemistry LibreTexts

Elsom, L. F. published the artcilePyrrole studies. XIV. Spectroscopic characteristics of cyanopyrroles, COA of Formula: C7H8N2, the publication is Journal of the Chemical Society [Section] B: Physical Organic (1970), 79-81, database is CAplus.

Data for pyrroles containing Me and CN groups show that the NH stretching frequency may be represented by the equation: νNH(cm-1) = 3496 – 9nαMe + 2nβMe – 22nαCN – 12nβCN, where nα and nβ are the number of substituents in the α- and β-positions resp. The electronic spectra indicate that in the excited state the resonance stabilization by the α-CN group is greater than that of the β-CN group to the extent of about 10.5 kcal/mole.

Journal of the Chemical Society [Section] B: Physical Organic published new progress about 26187-28-0. 26187-28-0 belongs to nitriles-buliding-blocks, auxiliary class Pyrrole,Nitrile, name is 2,4-Dimethyl-1H-pyrrole-3-carbonitrile, and the molecular formula is C7H8N2, COA of Formula: C7H8N2.

Referemce:
https://en.wikipedia.org/wiki/Nitrile,
Nitriles – Chemistry LibreTexts

Gibson, Charles S. published the artcileSyntheses with β,β’-dichlorodiethyl ether. I. Derivatives of tetrahydropyran, Computed Properties of 30431-99-3, the publication is Journal of the Chemical Society (1930), 2525-30, database is CAplus.

(ClCH₂CH₂)₂O (I), m. -24.5°, b₁₂ 66°, b₁₅ 70°, b₇₄₄ 176°, with a large excess of NaI in Me₂CO, gives the β,β’-diiododiethyl ether (II), b₁₀ 123.5-4°. I, CH₂(CO₂Et)₂ and Na in EtOH, boiled 5 hrs., give Et tetrahydropyran-4,4-dicarboxylate, b₁₂ 134-5°; hydrolysis with EtOH-KOH gives 81% of the acid, which loses CO₂ at 175-85°, giving 94.5% of tetrahydropyran-4-carboxylic acid (III), b₁₅ 146-7°; acid chloride, b₁₆ 85-6°; Me ester, b₁₆ 80.5-1°; Et ester, b₁₂ 82.5°; amide, m. 179°; anilide, m. 163°. I and NCCHNaCO₂Et in EtOH, heated 3 hrs. and kept 12 hrs., give 33% of Et 4-cyanotetrahydropyran-4-carboxylate, b₁₆ 125°; free acid, m. 160-2°; amide, in. 158°; heating at 180-200° for 1 hr. gives 66% of 4-cyanotetrahydropyran, b₁₀ 82-3°; this could not be reduced to the amine by Na in AmOH. I and AcCHNaCO₂Et gave only a small amount of high-boiling material. II gives a product b₉ 122.5-3.5°, which, on hydrolysis, gives III, AcOH and a trace of a ketone. No results were obtained in the Friedel-Crafts reaction with I and C₆H₆ or between I and KCN. I, As₂O₃ and NaOH gave no condensation product.

Journal of the Chemical Society published new progress about 30431-99-3. 30431-99-3 belongs to nitriles-buliding-blocks, auxiliary class Tetrahydropyran,Nitrile,Ester, name is Ethyl 4-cyanotetrahydro-2H-pyran-4-carboxylate, and the molecular formula is C9H13NO3, Computed Properties of 30431-99-3.

Referemce:
https://en.wikipedia.org/wiki/Nitrile,
Nitriles – Chemistry LibreTexts

Liu, Chunsheng published the artcileGreen synthesis process of fluorescent brightener ER, Category: nitriles-buliding-blocks, the publication is Ranliao Yu Ranse (2010), 47(5), 41-43, database is CAplus.

2-Cyanobenzyl chloride directly reacted with a slight excess of tri-Et phosphite by esterification reaction without adding other organic solvents, so the solvent recovery process was avoided. Using recrystallization mother liquor as the condensation reaction solvent, the process of solvent recovery was avoided also. The solvent loss and energy consumption were reduced by this process, and the yield of fluorescent brightener ER was increased by 10%. The green synthesis of fluorescent brightener ER was realized authentically.

Ranliao Yu Ranse published new progress about 612-13-5. 612-13-5 belongs to nitriles-buliding-blocks, auxiliary class Organic Pigment, name is 2-(Chloromethyl)benzonitrile, and the molecular formula is C8H6ClN, Category: nitriles-buliding-blocks.

Referemce:
https://en.wikipedia.org/wiki/Nitrile,
Nitriles – Chemistry LibreTexts

Xiao, Yuanyuan published the artcileEnantioselective Construction of Spiro Thiazol-4-one Derivatives with Multiple Stereocenters via an Organocatalyzed Multicomponent Cascade Reaction, Computed Properties of 5153-73-1, the publication is Advanced Synthesis & Catalysis (2018), 360(10), 1961-1966, database is CAplus.

An organocatalyzed asym. three-component reaction of thiazol-4-ones, acrolein and nitroolefins, which provides an efficient approach to access optically active spiro thiazol-4-ones I (R = C₆H₅, 4-FC₆H₄, 4-F₃CC₆H₄, etc.; R¹ = C₆H₅, 1-naphthyl, 2-thienyl, etc.) is developed. Under the catalysis of a bifunctional squaramide derived from L-tert-leucine, the reactions of a wide range of thiazol-4-ones, acrolein and nitroolefins took place smoothly to generate the corresponding spirothiazolone derivatives bearing four contiguous stereogenic centers in good yields with high levels of enantioselectivity. The title chiral spirothiazolones were obtained as a pair of separable epimers, which are formed through a double Michael addition followed by a Henry process.

Advanced Synthesis & Catalysis published new progress about 5153-73-1. 5153-73-1 belongs to nitriles-buliding-blocks, auxiliary class Nitrile,Alkenyl,Nitro Compound,Benzene, name is (E)-4-(2-Nitrovinyl)benzonitrile, and the molecular formula is C4H3Cl2N3, Computed Properties of 5153-73-1.

Referemce:
https://en.wikipedia.org/wiki/Nitrile,
Nitriles – Chemistry LibreTexts

Kuang, Dai-Zhi published the artcileSynthesis and crystal structure of tetra(o-cyanobenzyl)tin, Product Details of C8H6ClN, the publication is Chinese Journal of Structural Chemistry (2008), 27(1), 35-38, database is CAplus.

The tetra(o-cyanobenzyl)tin compound was synthesized by the reaction of cyanobenzyl chloride with tin, and its mol. structure was characterized by elemental anal., IR spectra, ¹H NMR and X-ray diffraction. Crystal data for this compound: monoclinic, space group C2/c, M_r = 583.24, a = 1.9629(2), b = 1.05967(13), c = 1.41249(18) nm, β = 118.180(2)°, V = 2.5898(5) nm³, Z = 4, D_c = 1.496 g/cm³, μ(MoKα) = 1.015 cm^-1, F(000) = 1176, R = 0.0189, wR = 0.0497 (observed reflections with I > 2σ(I)) and R = 0.0218, wR = 0.0513 (all reflections). The mol. structure adopts a distorted tetrahedral geometry around the tin atom. The Sn…N weak interaction between the Sn and N atoms of cyano forms an intermol. H-bonding, and the bond length is 0.3570 nm; the interaction between hydrogen of methylene and benzene ring of benzyl forms C-H…C with its bond length of 0.2817 nm; and the interaction among hydrogen of benzene ring and carbon of cyano forms Ph-H…C bond (0.2897 nm) of the σ…π interaction. A 3D chain structure is formed by the above weak intermol. interactions.

Chinese Journal of Structural Chemistry published new progress about 612-13-5. 612-13-5 belongs to nitriles-buliding-blocks, auxiliary class Organic Pigment, name is 2-(Chloromethyl)benzonitrile, and the molecular formula is C8H6ClN, Product Details of C8H6ClN.

Referemce:
https://en.wikipedia.org/wiki/Nitrile,
Nitriles – Chemistry LibreTexts