Tag: M.W=200-250

Jiang, Chao published the artcileCopper-catalyzed benzylic C-H bond thiocyanation: enabling late-stage diversifications, Recommanded Product: Bis(4-fluorophenyl)methane, the publication is CCS Chemistry (2021), 3(8), 1884-1893, database is CAplus.

The rapid growth of using C-H bond as cross-coupling partners is reshaping the landscape of organic synthesis. C(sp³)-H functionalization via hydrogen atom transfer (HAT) represents the most compelling strategy in this avenue. Here, authors demonstrate an efficient method for benzylic C-H bond thiocyanation via copper-catalyzed radical relay. The reaction exhibits broad substrate scope and exquisite benzylic selectivity with C-H substrates as limiting reagents. In addition, the benzyl thiocyanates are readily converted to other pharmaceutically important motifs, including isothiocyanate, thiourea, and others, highlighting the broad utility of this method.

CCS Chemistry published new progress about 457-68-1. 457-68-1 belongs to catalysis-chemistry, auxiliary class Fluoride,Benzene, name is Bis(4-fluorophenyl)methane, and the molecular formula is C13H10F2, Recommanded Product: Bis(4-fluorophenyl)methane.

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

Hu, Huayou published the artcileCopper-catalyzed benzylic C-H coupling with alcohols via radical relay enabled by redox buffering, Formula: C13H10F2, the publication is Nature Catalysis (2020), 3(4), 358-367, database is CAplus and MEDLINE.

Copper-catalyzed oxidative cross-coupling of benzylic C-H bonds with alcs. to afford benzyl ethers, enabled by a redox buffering strategy that maintains the activity of the copper catalyst throughout the reaction was reported. The reactions employ the C-H substrate as the limiting reagent and exhibit broad scope with respect to both coupling partners. This approach to direct site-selective functionalization of C(sp³)-H bonds provides the basis for efficient three-dimensional diversification of organic mols. and should find widespread utility in organic synthesis, particularly for medicinal chem. applications.

Nature Catalysis published new progress about 457-68-1. 457-68-1 belongs to catalysis-chemistry, auxiliary class Fluoride,Benzene, name is Bis(4-fluorophenyl)methane, and the molecular formula is C13H10F2, Formula: C13H10F2.

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

Suh, Sung-Eun published the artcileSite-Selective Copper-Catalyzed Azidation of Benzylic C-H Bonds, Product Details of C13H10F2, the publication is Journal of the American Chemical Society (2020), 142(26), 11388-11393, database is CAplus and MEDLINE.

Site selectivity represents a key challenge for non-directed C-H functionalization, even when the C-H bond is intrinsically reactive. Here, we report a copper-catalyzed method for benzylic C-H azidation of diverse mols. Exptl. and d. functional theory studies suggest the benzyl radical reacts with a Cu^II-azide species via a radical-polar crossover pathway. Comparison of this method with other C-H azidation methods highlights its unique site selectivity, and conversions of the benzyl azide products into amine, triazole, tetrazole, and pyrrole functional groups highlight the broad utility of this method for target mol. synthesis and medicinal chem.

Journal of the American Chemical Society published new progress about 457-68-1. 457-68-1 belongs to catalysis-chemistry, auxiliary class Fluoride,Benzene, name is Bis(4-fluorophenyl)methane, and the molecular formula is C18H34N4O5S, Product Details of C13H10F2.

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

Yang, Jia published the artcileC-P Bond-Forming Reactions via C-O/P-H Cross-Coupling Catalyzed by Nickel, Application of Allyldiphenylphosphine oxide, the publication is Journal of the American Chemical Society (2015), 137(5), 1782-1785, database is CAplus and MEDLINE.

The first Ni-catalyzed C-O/P-H cross-coupling producing organophosphorus compounds is disclosed. This method features wide generality in regard to both C-O and P-H compounds: for C-O compounds, the readily available alc. derivatives of aryl, alkenyl, benzyl, and allyl are applicable, and for P-H compounds, both >P^V(O)H compounds (secondary phosphine oxide, H-phosphinate, and H-phosphonate) and hydrogen phosphines (>P^IIIH) can be used as the substrates. Thus, a variety of valuable C(sp²)-P and C(sp³)-P compounds can be readily obtained in good to excellent yields by this new strategy.

Journal of the American Chemical Society published new progress about 4141-48-4. 4141-48-4 belongs to catalysis-chemistry, auxiliary class Aryl phosphine ligand,Mono-phosphine Ligands, name is Allyldiphenylphosphine oxide, and the molecular formula is C6H13BO3, Application of Allyldiphenylphosphine oxide.

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

Liao, Yu-Hua published the artcileOrganocatalytic asymmetric Michael addition of pyrazolin-5-ones to nitroolefins with bifunctional thiourea: stereocontrolled construction of contiguous quaternary and tertiary stereocenters, Related Products of catalysis-chemistry, the publication is Advanced Synthesis & Catalysis (2010), 352(5), 827-832, database is CAplus.

The first organocatalytic diastereo- and enantioselective Michael addition reaction of 4-substituted-pyrazolin-5-ones to nitroolefins was developed with a chiral bifunctional thiourea as organocatalyst. A wide variety of desired multi-substituted pyrazolin-5-one derivatives, e.g., I, with contiguous quaternary and tertiary stereocenters were smoothly obtained in good yields (up to 98%) with excellent enantioselectivities (up to >99% ee) and acceptable diastereoselectivities (up to 80:20). This exptl. simple process facilitated the access to various enantioenriched, multiply substituted pyrazolin-5-one derivatives, potential biol. active mols., starting from readily available starting materials.

Advanced Synthesis & Catalysis published new progress about 4230-93-7. 4230-93-7 belongs to catalysis-chemistry, auxiliary class Alkenyl,Nitro Compound,Benzene,Ether, name is 1,2-Dimethoxy-4-(2-nitrovinyl)benzene, and the molecular formula is C10H11NO4, Related Products of catalysis-chemistry.

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

Huang, Huang published the artcileI^–/TBHP catalyzed C_sp³-N/C_sp²-N bond formation via oxidative coupling with benzophenone imine in water, Quality Control of 457-68-1, the publication is Green Chemistry (2015), 17(10), 4715-4719, database is CAplus.

An I^–/TBHP catalyzed C_sp³-N/C_sp²-N bond formation via oxidative amination with benzophenone imine under environmentally benign conditions was developed. Several structurally diverse diarylmethanes, 3-subtituted indolin-2-ones and aldehydes underwent oxidative amination with benzophenone imine to afford the corresponding amines, e.g., I and II, or amides, e.g., III in good yields. The active iodine species were identified by well-designed control experiments for elucidating the mechanism.

Green Chemistry published new progress about 457-68-1. 457-68-1 belongs to catalysis-chemistry, auxiliary class Fluoride,Benzene, name is Bis(4-fluorophenyl)methane, and the molecular formula is C13H10F2, Quality Control of 457-68-1.

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

Qian, Jianchang published the artcileDesign and synthesis novel di-carbonyl analogs of curcumin (DACs) act as potent anti-inflammatory agents against LPS-induced acute lung injury (ALI), Application In Synthesis of 16909-09-4, the publication is European Journal of Medicinal Chemistry (2019), 414-425, database is CAplus and MEDLINE.

A novel series of di-carbonyl analogs of curcumin (DACs) were prepared and evaluated for their anti-inflammatory properties. Preliminary results showed that a vast majority of compounds tested in this study could effectively suppress LPS-induced production of tumor necrosis factor (TNF)-¦Á and interleukin (IL)-6. Structure-activity relationships of the compounds were discussed. Compounds I and II showed the most potent anti-inflammatory activities and had higher structural stability and orally bioavailability than curcumin in vitro. Mechanistically, they inhibited the activation of macrophages via the blockade of mitogen-activated protein kinase (MAPK) signaling and nuclear translocation of NF-¦ÊB. In vivo, I and II markedly alleviated lipopolysaccharides (LPS)-induced acute lung injury (ALI). The wet/dry ratio of lungs was significantly normalized by the active compounds, which was consistent with the suppression of neutrophil infiltration and production of proinflammatory cytokines. Collectively, these results present a new series of curcumin analogs as promising anti-inflammatory agents for treatment of ALI.

European Journal of Medicinal Chemistry 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

Guo, Jing published the artcileNovel Shikonin Derivatives Targeting Tubulin as Anticancer Agents, Application of 2-(4-(tert-Butyl)phenoxy)acetic acid, the publication is Chemical Biology & Drug Design (2014), 84(5), 603-615, database is CAplus and MEDLINE.

In this study, the authors report the identification of a new shikonin-phenoxyacetic acid derivative, as an inhibitor of tubulin. A series of compounds were prepared; among them, compound 16 [(R) -1 – (5, 8- dihydroxy-1, 4- dioxo-1, 4- dihydronaphthalen-2-yl)-4-methylpent-3-enyl 2- (4- phenoxyphenyl) acetate] potently inhibited the function of microtubules, inducing cell growth inhibition, apoptosis of cancer cell lines in a concentration and time-dependent manner. Mol. docking involving compound 16 at the vinblastine binding site of tubulin indicated that a phenoxy moiety interacted with tubulin via hydrogen bonding with asparaginate (Asn) and tyrosine (Tyr). Anal. of microtubules with confocal microscopy demonstrated that compound 16 altered the microtubule architecture and exhibited a significant reduction in microtubule d. Cell cycle assay further proved that HepG2 cells were blocked in G2/M phase. The authors’ study provides a new, promising compound for the development of tubulin inhibitors by proposing a new target for the anticancer activity of shikonin.

Chemical Biology & Drug Design published new progress about 1798-04-5. 1798-04-5 belongs to catalysis-chemistry, auxiliary class Carboxylic acid,Benzene,Ether, name is 2-(4-(tert-Butyl)phenoxy)acetic acid, and the molecular formula is C12H16O3, Application of 2-(4-(tert-Butyl)phenoxy)acetic acid.

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

Jullig, Mia published the artcileReversal of diabetes-evoked changes in mitochondrial protein expression of cardiac left ventricle by treatment with a copper(II)-selective chelator, Synthetic Route of 38260-01-4, the publication is Proteomics: Clinical Applications (2007), 1(4), 387-399, database is CAplus and MEDLINE.

Cardiac disease is the commonest cause of death amongst diabetic patients. Diabetic cardiomyopathy, which has a poor prognosis, is characterized by left ventricular hypertrophy and impaired cardiac function and mitochondrial damage is said to contribute to its development. We recently showed that treatment with the Cu^II-selective chelator, triethylenetetramine (TETA), improved cardiac structure, and function in diabetic subjects without modifying hyperglycemia. Thus, TETA has potential utility for the treatment of heart disease. To further understand the mol. mechanism by which it causes these effects, we have conducted the first study of the effect of oral TETA on protein abundance in the cardiac left ventricle of rats with severe streptozotocin-induced diabetes. Proteomic methods showed that of 211 proteins changed in diabetes, 33 recovered after treatment. Through MS, 16 proteins were identified which may constitute major targets of drug action. Remarkably, most of these were mitochondrial proteins with roles in energy metabolism In addition to components of the mitochondrial respiratory chain and enzymes involved in fatty acid oxidation, TETA treatment normalized both myocardial expression and enzymic activity of carnitine palmitoyltransferase 2. These findings indicate that mitochondria constitute major targets in the mechanism by which TETA restores cardiac structure and function in diabetes.

Proteomics: Clinical Applications published new progress about 38260-01-4. 38260-01-4 belongs to catalysis-chemistry, auxiliary class Chelating Agents, name is N1,N1′-(Ethane-1,2-diyl)bis(ethane-1,2-diamine) dihydrochloride, and the molecular formula is C6H20Cl2N4, Synthetic Route of 38260-01-4.

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

Ma, Chicheng published the artcilePhotochemical Cleavage and Release of Para-Substituted Phenols from ¦Á-Keto Amides, Safety of 2-(4-(Trifluoromethyl)phenoxy)acetic acid, the publication is Journal of Organic Chemistry (2006), 71(11), 4206-4215, database is CAplus and MEDLINE.

In aqueous media ¦Á-keto amides 4-YC₆H₄OCH₂COCON(R)CH(R’)CH₃ (5a, R = Et, R’ = H; 5b, R = ⁱPr, R’ = Me) with para-substituted phenolic substituents (Y = CN, CF₃, H) undergo photocleavage and release of 4-YC₆H₄OH with formation of 5-methyleneoxazolidin-4-ones 7a,b. For both 5a,b quantum yields range from 0.2 to 0.3. The proposed mechanism involves transfer of hydrogen from an N-alkyl group to the keto oxygen to produce zwitterionic intermediates 8a–c that eliminate the para-substituted phenolate leaving groups. The resultant iminium ions H₂C:C(OH)CON⁺(R):C(R’)CH₃?9a,b cyclize intramolecularly to give 7a,b. The quantum yields for photoelimination decrease in CH₃CN, CH₂Cl₂, or C₆H₆ due to competing cyclization of 8a,b to give oxazolidin-4-one products which retain the leaving group 4-YC₆H₄O^– (Y = H, CN). A greater tendency to undergo cyclization in nonaqueous media is observed for the N,N-di-Et amides 5a than the N,N-diisopropyl amides 5b. With para electron releasing groups Y = CH₃ and OCH₃ quantum yields for photoelimination significantly decrease and 1,3-photorearrangement of the phenolic group is observed The 1,3-rearrangement involves excited state ArO-C bond homolysis to give para-substituted phenoxyl radicals, which can be observed directly in laser flash photolysis experiments

Journal of Organic Chemistry published new progress about 163839-73-4. 163839-73-4 belongs to catalysis-chemistry, auxiliary class Trifluoromethyl,Fluoride,Carboxylic acid,Benzene,Ether, name is 2-(4-(Trifluoromethyl)phenoxy)acetic acid, and the molecular formula is C9H7F3O3, Safety of 2-(4-(Trifluoromethyl)phenoxy)acetic acid.

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