Month: November 2022

Giel, Marie-Claire published the artcileAminium cation-radical catalyzed selective hydration of (E)-aryl enynes, Application In Synthesis of 16909-09-4, the publication is Chemical Communications (Cambridge, United Kingdom) (2021), 57(57), 6991-6994, database is CAplus and MEDLINE.

The hydration of carbon-carbon triple bonds is an important and atom economic synthetic transformation. Herein, authors report a mild and selective method for the catalytic Markovnikov hydration of (E)-aryl enynes to the corresponding enones, mediated through the bench-stable aminium salt, tris(4-bromophenyl)ammoniumyl hexachloroantimonate (TBPA). The chemoselective and diastereoselective method proceeds under neutral metal-free conditions, delivering excellent product yields from terminal and internal alkyne units. The synthesis of biol. important (E)-3-styrylisocoumarins, including a formal synthesis of the natural product achlisocoumarin III, demonstrates the utility of this novel transformation.

Chemical Communications (Cambridge, United Kingdom) published new progress about 16909-09-4. 16909-09-4 belongs to catalysis-chemistry, auxiliary class Alkenyl,Carboxylic acid,Benzene,Ether, name is (E)-3-(2,4-Dimethoxyphenyl)acrylic acid, and the molecular formula is C11H12O4, Application In Synthesis of 16909-09-4.

Referemce:
https://courses.lumenlearning.com/boundless-chemistry/chapter/catalysis/,
Catalysis – Wikipedia

Shaghafi, Michael B. published the artcileThe insulin secretory action of novel polycyclic guanidines: Discovery through open innovation phenotypic screening, and exploration of structure-activity relationships, Safety of (E)-3-(3-Nitrophenyl)acrylic acid, the publication is Bioorganic & Medicinal Chemistry Letters (2014), 24(4), 1031-1036, database is CAplus and MEDLINE.

We report the discovery of the glucose-dependent insulin secretogogue activity of a novel class of polycyclic guanidines through phenotypic screening as part of the Lilly Open Innovation Drug Discovery platform. Three compounds from the University of California, Irvine, I.HCl, II.HCl and III.HCl, having the 3-arylhexahydropyrrolo[1,2-c]pyrimidin-1-amine scaffold acted as insulin secretagogues under high, but not low, glucose conditions. Exploration of the structure-activity relationship around the scaffold demonstrated the key role of the guanidine moiety, as well as the importance of two lipophilic regions, and led to the identification of IV.HCl, which stimulated insulin secretion in isolated rat pancreatic islets in a glucose-dependent manner.

Bioorganic & Medicinal Chemistry Letters published new progress about 1772-76-5. 1772-76-5 belongs to catalysis-chemistry, auxiliary class Benzenes, name is (E)-3-(3-Nitrophenyl)acrylic acid, and the molecular formula is C15H21BO3, Safety of (E)-3-(3-Nitrophenyl)acrylic acid.

Referemce:
https://courses.lumenlearning.com/boundless-chemistry/chapter/catalysis/,
Catalysis – Wikipedia

Krishnamurti, Vinayak published the artcileAqueous Base Promoted O-Difluoromethylation of Carboxylic Acids with TMSCF₂Br: Bench-Top Access to Difluoromethyl Esters, Quality Control of 119-80-2, the publication is Organic Letters (2019), 21(23), 9377-9380, database is CAplus and MEDLINE.

A method for the O-difluoromethylation of carboxylic acids using com. available TMSCF₂Br is disclosed. The devised bench-top reaction system is air-stable and offers mild reaction conditions while using readily available reagents and solvents. The method is applicable to both aliphatic and aromatic carboxylic acids while demonstrating compatibility with a range of commonly encountered functional groups. The difluoromethyl esters of FDA approved drugs and pharmaceutically relevant mols. are also presented, demonstrating the potential for late-stage functionalization.

Organic Letters published new progress about 119-80-2. 119-80-2 belongs to catalysis-chemistry, auxiliary class sulfides,Carboxylic acid,Benzene, name is 2,2′-Dithiodibenzoic acid, and the molecular formula is C14H10O4S2, Quality Control of 119-80-2.

Referemce:
https://courses.lumenlearning.com/boundless-chemistry/chapter/catalysis/,
Catalysis – Wikipedia

Maldonado-Pereira, Lisaura published the artcileEvaluation of the nutritional quality of ultra-processed foods (ready to eat + fast food): Fatty acids, sugar, and sodium, Application of Docosahexaenoic Acid, the publication is Journal of Food Science (2022), 87(8), 3659-3676, database is CAplus and MEDLINE.

The average American consumes more than 50% of their total dietary energy from ultra-processed foods (UPFs). From a nutritional standpoint, as UPFs intake increases, fiber, vitamin, and mineral intake decrease. High consumption of UPFs, mainly from fast foods (FF) and ready-to-eat (RTE) food items, emerges as a critical public health concern linking nutritional quality and food safety. In the present work, a systematic database of the fatty acid composition of the most consumed UPFs in the Midwest is reported. Saturated and monounsaturated fatty acids were predominant in RTE (42.5%) and FF (43.2%), resp. In addition, the fatty acid profile in UPFs is reported according to six food categories: meat and poultry, eggs and derivatives, dairy products, seafood, baby foods, and others. Meat and poultry, and dairy products were the dominant food categories among UPFs. Meanwhile, polyunsaturated fatty acids were abundant in the eggs and seafood groups UPFs (61.8% and 46.4%, resp.) regardless of the food group. Furthermore, no significant differences were found in sugar content in UPFs. Caloric content was pos. correlated with sodium (ρ = 0.748) and price (ρ = 0.534). The significance of this study relies on providing new quant. data on the fat, sodium, and sugar contents of the most consumed UPFs in the Midwestern area of the United States. This information suggests paying more attention to these nutritional attributes, aiming to reduce their incorporation in UPF preparations Addnl., more quant. data are needed regarding other nutritional parameters such as protein and lipid degradation in UPFs.

Journal of Food Science published new progress about 6217-54-5. 6217-54-5 belongs to catalysis-chemistry, auxiliary class Alkenyl,Carboxylic acid,Aliphatic hydrocarbon chain,Metabolic Enzyme,RAR/RXR,Natural product, name is Docosahexaenoic Acid, and the molecular formula is C22H32O2, Application of Docosahexaenoic Acid.

Referemce:
https://courses.lumenlearning.com/boundless-chemistry/chapter/catalysis/,
Catalysis – Wikipedia

Cunningham, Drew W. published the artcileReversible and Selective CO₂ to HCO₂^– Electrocatalysis near the Thermodynamic Potential, Quality Control of 17351-62-1, the publication is Angewandte Chemie, International Edition (2020), 59(11), 4443-4447, database is CAplus and MEDLINE.

Reversible catalysis is a hallmark of energy-efficient chem. transformations, but can only be achieved if the changes in free energy of intermediate steps are minimized and the catalytic cycle is devoid of high transition-state barriers. Using these criteria, the authors demonstrate reversible CO₂/HCO₂^– conversion catalyzed by [Pt(depe)₂]²⁺ (depe = 1,2-bis(diethylphosphino)ethane). Direct measurement of the free energies associated with each catalytic step correctly predicts a slight bias towards CO₂ reduction The exptl. measured free energy of each step directly contributes to the <50 mV overpotential. Also for CO₂ reduction, H₂ evolution is negligible and the faradaic efficiency for HCO₂^– production is nearly quant. A free-energy anal. reveals H₂ evolution is endergonic, providing a thermodn. basis for highly selective CO₂ reduction

Angewandte Chemie, International Edition published new progress about 17351-62-1. 17351-62-1 belongs to catalysis-chemistry, auxiliary class Salt,Amine, name is Tetrabutylammonium hydrogencarbonate, and the molecular formula is C17H37NO3, Quality Control of 17351-62-1.

Referemce:
https://courses.lumenlearning.com/boundless-chemistry/chapter/catalysis/,
Catalysis – Wikipedia

Shmakov, Mikhail M. published the artcilePreparation of heptafluoronaphthyllithiums and -magnesiums: An unexpected difference in the reactivity of isomers C₁₀F₇H and C₁₀F₇Br towards organolithium and organomagnesium compounds, SDS of cas: 1206-46-8, the publication is Journal of Organometallic Chemistry (2019), 120889, database is CAplus.

Significant differences in the reactivity of isomeric heptafluoronaphthalenes and bromoheptafluoronaphthalenes towards organolithium and organomagnesium compounds were found. Metalation of polyfluorinated naphthalenes 2-C₁₀F₇X (X = H, Br) occurs easily under the action of bases (BuLi, t-BuLi, LDA) as well as EtMgBr (X = Br) in ether. This fact was proven by ¹⁹F NMR spectroscopy and by trapping of 2-C₁₀F₇M (M = Li, MgBr, Mg(2-C₁₀F₇)) with electrophile ClSiMe₃. The interaction of 1-C₁₀F₇Br with BuLi or EtMgBr proceeds in a similar way. In contrast to 2-C₁₀F₇H, isomeric 1-C₁₀F₇H is the less acidic substrate and undergoes only the nucleophilic alkyldefluorination when combined with BuLi or t-BuLi.

Journal of Organometallic Chemistry published new progress about 1206-46-8. 1206-46-8 belongs to catalysis-chemistry, auxiliary class Organic Silicones, name is Trimethyl(perfluorophenyl)silane, and the molecular formula is C8H5F3N4, SDS of cas: 1206-46-8.

Referemce:
https://courses.lumenlearning.com/boundless-chemistry/chapter/catalysis/,
Catalysis – Wikipedia

Frohn, Hermann-Josef published the artcileExplored routes to unknown polyfluoroorganyliodine hexafluorides, R_FIF₆, Product Details of C9H9F5Si, the publication is Journal of Fluorine Chemistry (2010), 131(10), 1000-1006, database is CAplus.

Two routes to R_FIF₆ compounds were investigated: (a) the substitution of F by R_F in IF₇ and (b) the fluorine addition to iodine in R_FIF₄ precursors. For route (a) the reagents C₆F₅SiMe₃, C₆F₅SiF₃, [NMe₄][C₆F₅SiF₄], C₆F₅BF₂, and 1,4-C₆F₄(BF₂)₂ were tested. C₆F₅IF₄ and CF₃CH₂IF₄ were used in route (b) and treated with the fluoro-oxidizers IF₇, [O₂][SbF₆]/KF, and K₂[NiF₆]/KF. The observed sidestep reactions in case of routes (a) and (b) are discussed. Interaction of C₆F₅SiX₃ (X = Me, F), C₆F₅BF₂, 1,4-C₆F₄(BF₂)₂ with IF₇ gave exclusively the corresponding ring fluorination products, perfluorinated cyclohexadiene and cyclohexene derivatives, whereas [NMe₄][C₆F₅SiF₄] and IF₇ formed mixtures of C₆F_nIF₄ and C₆F_nH compounds (n = 7 and 9). CF₃CH₂IF₄ was not reactive towards the fluoro-oxidizer IF₇, whereas C₆F₅IF₄ formed C₆F_nIF₄ compounds (n = 7 and 9). C₆F₅IF₄ and CF₃CH₂IF₄ were inert towards [O₂][SbF₆] in anhydrous HF. CF₃CH₂IF₄ underwent C-H fluorination and C-I bond cleavage when treated with K₂[NiF₆]/KF in HF. The fluorine addition property of IF₇ was independently demonstrated in case of perfluorohexenes. C₄F₉CF=CF₂ and IF₇ underwent oxidative fluorine addition at -30 °C, and the isomers (CF₃)₂CFCF=CFCF₃ (cis and trans) formed very slowly perfluoroisohexanes even at 25 °C. The compatibility of IF₇ and selected organic solvents was investigated. The polyfluoroalkanes CF₃CH₂CHF₂ (PFP), CF₃CH₂CF₂CH₃ (PFB), and C₄F₉Br are inert towards iodine heptafluoride at 25 °C while CF₃CH₂Br was slowly converted to CF₃CH₂F. Especially PFP and PFB are new suitable organic solvents for IF₇.

Journal of Fluorine Chemistry published new progress about 1206-46-8. 1206-46-8 belongs to catalysis-chemistry, auxiliary class Organic Silicones, name is Trimethyl(perfluorophenyl)silane, and the molecular formula is C9H9F5Si, Product Details of C9H9F5Si.

Referemce:
https://courses.lumenlearning.com/boundless-chemistry/chapter/catalysis/,
Catalysis – Wikipedia

Petrov, V. A. published the artcileReaction of (pentafluorophenyl)trimethylsilane with perfluorinated internal azaalkenes in the presence of cesium fluoride, Name: Trimethyl(perfluorophenyl)silane, the publication is Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya (1990), 923-4, database is CAplus.

CF₃(CF₂)_mN:CF(CF₂)_nCF₃ (m = 1, n = 0; m = 3, n = 2) reacted with C₆F₅SiMe₃ in the presence of CsF to give 63 and 56% yields, resp., of CF₃(CF₂)_mN:C(C₆F₅)(CF₂)_nCF₃.

Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya published new progress about 1206-46-8. 1206-46-8 belongs to catalysis-chemistry, auxiliary class Organic Silicones, name is Trimethyl(perfluorophenyl)silane, and the molecular formula is C9H9F5Si, Name: Trimethyl(perfluorophenyl)silane.

Referemce:
https://courses.lumenlearning.com/boundless-chemistry/chapter/catalysis/,
Catalysis – Wikipedia

Espadinha, Margarida published the artcileTryptophanol-derived oxazolopyrrolidone lactams as potential anticancer agents against gastric adenocarcinoma, COA of Formula: C10H10O3, the publication is Pharmaceuticals (2021), 14(3), 208, database is CAplus and MEDLINE.

Gastric cancer is one of the deadliest cancers in modern societies, so there is a high level of interest in discovering new drugs for this malignancy. Previously, we demonstrated the ability of tryptophanol-derived polycyclic compounds to activate the tumor suppressor protein p53, a relevant therapeutic target in cancer. In this work, we developed a novel series of enantiomerically pure tryptophanol-derived small mols. to target human gastric adenocarcinoma (AGS) cells. From an initial screening of fourteen compounds in AGS cell line, a hit compound was selected for optimization, leading to two derivatives selective for AGS gastric cells over other types of cancer cells (MDA-MB-231, A-549, DU-145, and MG-63). More importantly, the compounds were non-toxic in normal cells (HEK 293T). Addnl., we show that the growth inhibition of AGS cells induced by these compounds is mediated by apoptosis. Stability studies in human plasma and human liver microsomes indicate that the compounds are stable, and that the major metabolic transformations of these mols. are mono- and di-hydroxylation of the indole ring.

Pharmaceuticals published new progress about 2051-95-8. 2051-95-8 belongs to catalysis-chemistry, auxiliary class Carboxylic acid,Benzene,Ketone, name is 3-Benzoylpropionicacid, and the molecular formula is C10H10O3, COA of Formula: C10H10O3.

Referemce:
https://courses.lumenlearning.com/boundless-chemistry/chapter/catalysis/,
Catalysis – Wikipedia

Arndt, R. R. published the artcileAutoxidation. I. Liquid phase autoxidation of 5-methylnonane, Category: catalysis-chemistry, the publication is Journal of the Chemical Society (1959), 3258-64, database is CAplus.

The purpose was to determine the effect of a Me group, introduced into an otherwise straight-chain hydrocarbon, on the position of radical attack during autoxidation 5-Methylnonane (I), b₆₅₅ 160°, n²¹_D 1.4122, was prepared Bu₂C(OH)Me (500 g.), b₂₄ 103-4°, n²⁵_D 1.4328, was slowly distilled over 0.1 g. iodine at atm. pressure. The distillate was dried over CaCl₂ and redist. to give 5-methyl-4-nonene (II), b₆₅₅ 155-6°. Hydrogenation of II at 100° and 150 lb./sq. in. in the presence of 2% Pd(CaCO₃ yielded I (after fractional distillation). I was oxidized in O at 90°. Samples were withdrawn at intervals and reduced with LiAlH₄ to give a mixture of corresponding alcs., which were analyzed by gas chromatography (flame ionization detector). Mixtures of 3- and 4-ols could not be resolved by gas chromatography, but the mixture of isomers in the fraction was determined by infrared absorption spectroscopy. The susceptibility of various carbon positions to attack was in the expected order (tertiary > secondary > primary). However, differences in the reactivity of secondary C’s were observed. Position 2 was slightly more reactive than 4, and both were 2-3 times as reactive as position 3. H was removed 19 times more readily from a tertiary than a secondary C and 4 times more readily from a secondary than a primary C. As oxidation proceeded, chain fission of the primary oxidation product (5-hydroperoxy-5-methylnonane) yielded EtOH, BuOH, and 2-hexanol as major substances. Removal of the Me group from I did not take place, since the expected alc. was not detected. Diols obtained on reduction of disubstituted autoxidation products were found in substantial amounts, indicating that the chain reaction step ROOâ€?+ HR â†?ROOH + •R was propagated to a large extent by intramolecular H transfer. A number of possible reduction products were synthesized in order to identify the gas chromatographic peaks. 5-Methyl-4-nonanone, prepared by a Grignard reaction from 2-methylhexanoyl chloride and PrBr, was reduced with LiAlH₄, distilled, and purified by chromatography on alumina to yield 5-methyl-4-nonanol, b₆₅₄ 197.8-8.0°, n²⁵_D 1.4340, n³⁰_D 1.4320. 5-Methyl-3-nonanone, b₆₅₅ 194-6, prepared from 3-methylheptanoyl chloride and EtBr, gave 5-methyl-3-nonanol, b₆₅₅ 197.5-7.6°, n²⁶_D 1.4326, n³⁰_D 1.4312. Similarly prepared was 5-methyl-2-nonanol, b₆₅₅ 202-2.1°, n²⁵_D 1.4320, n³⁰_D 1.4312. 5-Methylnonanol, n³⁰_D 1.4340, was prepared by reduction of a 5-methylnonanoate with LiAlH₄. 2-Butylhexanol, b₆₅₅ 209.40, n³⁰_D 1.4328, was prepared by LiAlH₄ reduction of 2-butylhexanoic acid, b₃₅ 160-2°, n³⁰_D 1.4396. 5-Methyl-2,5-nonanediol, b_0.25 93°, m. 70°, was prepared from 5-oxo-2-hexanol and the Grignard derivative of BuBr. Similarly prepared was 5-methyl-3,5-nonanediol, b_0.1 77.5°, n³⁰_D 1.4407. Hydroxylation of 5-methyl-4-nonene with performic acid yielded 5-methyl-4,5-nonanediol, b_0.5 86°, n³⁰_D 1.4463.

Journal of the Chemical Society published new progress about 3115-28-4. 3115-28-4 belongs to catalysis-chemistry, auxiliary class Aliphatic Chain, name is 2-Butylhexanoic acid, and the molecular formula is C10H20O2, Category: catalysis-chemistry.

Referemce:
https://courses.lumenlearning.com/boundless-chemistry/chapter/catalysis/,
Catalysis – Wikipedia