Catalysis-chemistry

Vercammen, Jannick published the artcileShape-selective C-H activation of aromatics to biarylic compounds using molecular palladium in zeolites, Recommanded Product: 4,4′-Dimethyldiphenyl, the publication is Nature Catalysis (2020), 3(12), 1002-1009, database is CAplus.

The selective activation of inert C-H bonds has emerged as a promising tool for avoiding the use of wasteful traditional coupling reactions. Oxidative coupling of simple aromatics allows for a cost-effective synthesis of biaryls. However, utilization of this technol. is severely hampered by poor regioselectivity and by the limited stability of state-of-the-art homogeneous Pd catalysts. Here, we show that confinement of cationic Pd in the pores of a zeolite allows for the shape-selective C-H activation of simple aromatics without a functional handle or electronic bias. For instance, out of six possible isomers, 4,4′-bitolyl is produced with high shape selectivity (80%) in oxidative toluene coupling on Pd-Beta. Not only is a robust, heterogeneous catalytic system obtained, but this concept is also set to control the selectivity in transition-metal-catalyzed arene C-H activation through spatial confinement in zeolite pores.

Nature Catalysis published new progress about 613-33-2. 613-33-2 belongs to catalysis-chemistry, auxiliary class Benzene, name is 4,4′-Dimethyldiphenyl, and the molecular formula is C15H20O6, Recommanded Product: 4,4′-Dimethyldiphenyl.

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

Das, Shoubhik published the artcileMetal-Free Catalyst for the Chemoselective Methylation of Amines Using Carbon Dioxide as a Carbon Source, Recommanded Product: 2,6-Diisopropyl-N,N-dimethylaniline, the publication is Angewandte Chemie, International Edition (2014), 53(47), 12876-12879, database is CAplus and MEDLINE.

N-methylation of amines is an important step in the synthesis of many pharmaceuticals and has been widely applied in the preparation of other key intermediates and chems. Therefore, the development of efficient methylation methods has attracted considerable attention. In this respect, carbon dioxide is an attractive C₁ building block because it is an abundant, renewable, and nontoxic carbon source. Consequently, we developed a highly chemoselective, metal-free catalytic system that operates under ambient conditions for the N-methylation of amines.

Angewandte Chemie, International Edition published new progress about 2909-77-5. 2909-77-5 belongs to catalysis-chemistry, auxiliary class Amine,Benzene, name is 2,6-Diisopropyl-N,N-dimethylaniline, and the molecular formula is C14H23N, Recommanded Product: 2,6-Diisopropyl-N,N-dimethylaniline.

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

Bolsman, T. A. B. M. published the artcileCatalytic inhibition of hydrocarbon autoxidation by secondary amines and nitroxides, Recommanded Product: Bis(4-nitrophenyl)amine, the publication is Recueil des Travaux Chimiques des Pays-Bas (1978), 97(12), 310-12, database is CAplus.

The catalytic inhibition of autoxidation of hydrocarbons at 130° by secondary amines and their hydroxylamine and nitroxide derivatives was studied. Owing to a better resistance towards side-reactions that cause decomposition of the inhibitor, certain dialkylamines are much more efficient than diarylamines. Some of the dialkylamines examined are capable of scavenging several hundred propagating radicals per mol. of inhibitor in autoxidizing alkanes and a few thousand radicals in autoxidizing n-C₆H₁₃Ph.

Recueil des Travaux Chimiques des Pays-Bas published new progress about 1821-27-8. 1821-27-8 belongs to catalysis-chemistry, auxiliary class Nitro Compound,Amine,Benzene, name is Bis(4-nitrophenyl)amine, and the molecular formula is C12H9N3O4, Recommanded Product: Bis(4-nitrophenyl)amine.

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

Baechler, Raymond D. published the artcileContrasting thermal reactions of allylic sulfilimines and phosphinimines, Category: catalysis-chemistry, the publication is Tetrahedron Letters (1988), 29(42), 5353-4, database is CAplus.

Allylic sulfilimines and phosphinimines undergo spontaneous but contrasting rearrangements at low temperatures Whereas PhN:SPhCH₂CH:CH₂ is converted to isomeric sulfenamide PhN(SPh)CH₂CH:CH₂ by (2,3)-sigmatropic rearrangement, structurally analogous phosphinimine PhN:PPh₂CH₂CH:CH₂ undergoes an unusually facile double bond shift to form PhN:PPh₂CH:CHMe with an isomeric vinylic structure.

Tetrahedron Letters 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 C15H15OP, Category: catalysis-chemistry.

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

Schneider, Hans Joerg published the artcileInteraction of acyclic and cyclic peralkylammonium compounds and DNA, Safety of Propane-1,3-diamine dihydrochloride, the publication is Angewandte Chemie (1992), 104(9), 1244-6 (See also Angew. Chem., Int. Ed. Engl., 1992, 31(9), 1207-9), database is CAplus.

Electrostatic binding of calf thymus B-DNA by amines was studied with regard to amine structure in the binding mechanism. Free energies of binding by various amines were compared. DNA binding response to amine protonation and alkyl chain length and flexibility were considered. Acyclic and macrocyclic polyammonium derivatives were used as models, and biol. polyamines were discussed.

Angewandte Chemie published new progress about 10517-44-9. 10517-44-9 belongs to catalysis-chemistry, auxiliary class Salt,Amine,Aliphatic hydrocarbon chain, name is Propane-1,3-diamine dihydrochloride, and the molecular formula is C3H12Cl2N2, Safety of Propane-1,3-diamine dihydrochloride.

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

Collins, Jon L. published the artcileN-(2-Benzoylphenyl)-L-tyrosine PPARγ Agonists. 2. Structure-Activity Relationship and Optimization of the Phenyl Alkyl Ether Moiety, Safety of 1,1-Dimethylthiourea, the publication is Journal of Medicinal Chemistry (1998), 41(25), 5037-5054, database is CAplus and MEDLINE.

We previously reported the identification of (2S)-((2-benzoylphenyl)amino)-3-{4-[2-(5-methyl-2-phenyloxazol-4-yl)ethoxy]phenyl}propanoic acid (I) (PPARγ pK_i = 8.94, PPARγ pEC₅₀ = 9.47) as a potent and selective PPARγ agonist. We now report the expanded structure-activity relationship around the Ph alkyl ether moiety by pursuing both a classical medicinal chem. approach and a solid-phase chem. approach for analog synthesis. The solution-phase strategy focused on evaluating the effects of oxazole and Ph ring replacements of the 2-(5-methyl-2-phenyloxazol-4-yl)ethyl side chain of I with several replacements providing potent and selective PPARγ agonists with improved aqueous solubility Specifically, replacement of the Ph ring of the phenyloxazole moiety with a 4-pyridyl group to give (2S)-((2-benzoylphenyl)amino)-3-{4-[2-(5-methyl-2-pyridin-4-yloxazol-4-yl)ethoxy]phenyl}propionic acid (PPARγ pK_i = 8.85, PPARγ pEC₅₀ = 8.74) or a 4-methylpiperazine to give (2S)-((2-benzoylphenyl)amino)-3-(4-{2-[5-methyl-2-(4-methylpiperazin-1-yl)thiazol-4-yl]ethoxy}phenyl)propionic acid (PPARγ pK_i = 8.66, PPARγ pEC₅₀ = 8.89) provided two potent and selective PPARγ agonists with increased solubility in pH 7.4 phosphate buffer and simulated gastric fluid as compared to I. The second strategy took advantage of the speed and ease of parallel solid-phase analog synthesis to generate a more diverse set of Ph alkyl ethers which led to the identification of a number of novel, high-affinity PPARγ ligands (PPARγ pK_i‘s 6.98-8.03). The combined structure-activity data derived from the two strategies provide valuable insight on the requirements for PPARγ binding, functional activity, selectivity, and aqueous solubility

Journal of Medicinal Chemistry published new progress about 6972-05-0. 6972-05-0 belongs to catalysis-chemistry, auxiliary class Thiourea,Amine,Aliphatic hydrocarbon chain,Amide, name is 1,1-Dimethylthiourea, and the molecular formula is C3H8N2S, Safety of 1,1-Dimethylthiourea.

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

Cheng, Stephen C. published the artcileElectrochemical and IR Spectroelectrochemical Studies of the Electrocatalytic Reduction of Carbon Dioxide by [Ir₂(dimen)₄]²⁺ (dimen = 1,8-Diisocyanomenthane), Formula: C17H37NO3, the publication is Inorganic Chemistry (1996), 35(26), 7704-7708, database is CAplus.

The electrocatalytic reactions of carbon dioxide that are catalyzed by [Ir₂(dimen)₄]²⁺ (dimen = 1,8-diisocyanomenthane) were studied with cyclic voltammetry and IR spectroelectrochem. The hexafluorophosphate (PF₆^–) salt and the tetraphenylborate (BPh₄^–) salt are electrocatalysts for carbon dioxide reduction IR spectroelectrochem. allowed the identification of the carbon dioxide reduction products and provided information about the mechanism(s) of the reduction Bicarbonate and formate were identified as the electrocatalytic carbon dioxide reaction products by comparing the IR bands observed by spectroelectrochem. with authentic samples of tetrabutylammonium formate, tetrabutylammonium oxalate, and tetrabutylammonium bicarbonate. Formate arises from a net two-electron reduction of carbon dioxide that produces free formate and a formate complex of [Ir₂(dimen)₄]²⁺. Bicarbonate results from the reaction of hydroxide (produced when residual water is reduced to hydrogen) with carbon dioxide.

Inorganic Chemistry 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, Formula: C17H37NO3.

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

McInnis, Christine E. published the artcileNon-native N-Aroyl L-Homoserine Lactones Are Potent Modulators of the Quorum Sensing Receptor RpaR in Rhodopseudomonas palustris, Application of (E)-3-(3-Nitrophenyl)acrylic acid, the publication is ChemBioChem (2014), 15(1), 87-93, database is CAplus and MEDLINE.

Quorum sensing (QS) is a process by which bacteria use low-mol.-weight signaling mols. (or autoinducers) to assess their local population densities and alter gene expression levels at high cell numbers Many Gram-neg. bacteria use N-acyl L-homoserine lactones (AHLs) with aliphatic acyl groups as signaling mols. for QS. However, bacteria that use AHLs with aroyl acyl groups have been recently discovered; they include the metabolically versatile soil bacterium Rhodopseudomonas palustris, which uses p-coumaroyl HL (p-cAHL) as its QS signal. This autoinducer is especially unusual because its acyl group is believed to originate from a monolignol (i.e., p-coumarate) produced exogenously by plants in the R. palustris environment, rather than through the endogenous fatty acid biosynthesis pathway like other native AHLs. As such, p-cAHL could signal not only bacterial d., but also the availability of an exogenous plant-derived substrate and might even constitute an interkingdom signal. Like other Gram-neg. bacteria, QS in R. palustris is controlled by the p-cAHL signal binding its cognate LuxR-type receptor, RpaR. The authors sought to determine if non-native aroyl HLs (ArHLs) could potentially activate or inhibit RpaR in R. palustris, and thereby modulate QS in this bacterium. Herein, the authors report the testing of a set of synthetic ArHLs for RpaR agonism and antagonism by using a R. palustris reporter strain. Several potent non-native RpaR agonists and antagonists were identified. Addnl., the screening data revealed that lower concentrations of ArHL are required to strongly agonize RpaR than to antagonize it. Structure-activity relation analyses of the active ArHLs indicated that potent RpaR agonists tend to have sterically small substituents on their aryl groups, most notably in the ortho position. In turn, the most potent RpaR antagonists were based on either the phenylpropionyl HL (PPHL) or the phenoxyacetyl HL (POHL) scaffold, and many contained an electron-withdrawing group at either the meta or para positions of the aryl ring. To the authors’ knowledge, the compounds reported herein represent the first abiotic chem. modulators of RpaR, and more generally, the first abiotic ligands capable of intercepting QS in bacteria that use native ArHL signals. In view of the origins of the p-cAHL signal in R. palustris, the largely unknown role of QS in this bacterium, and R. palustris’ unique environmental lifestyles, the authors anticipate that these compounds could be valuable as chem. probes to study QS in R. palustris in a range of fundamental and applied contexts.

ChemBioChem 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 C9H7NO4, Application of (E)-3-(3-Nitrophenyl)acrylic acid.

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

Wester, Anita published the artcileEvaluation of 1H-Triazole-1-[N,N’-bis(tert-butoxycarbonyl)]carboxamidine in solution-phase and on-resin guanidinylation, Related Products of catalysis-chemistry, the publication is Journal of Organic Chemistry (2021), 86(21), 14371-14380, database is CAplus and MEDLINE.

Several guanidines and guanidinylated peptides have substantial potential as therapeutics, but efficient guanidinylation reagents are vital for easy access to these compounds Presently, pyrazole-1-carboxamidine type reagents are commonly used in the transformations of amines into corresponding guanidines. Here, we report a comparative study of the utility of 1H-triazole-1-[N,N’-bis(tert-butoxycarbonyl)]carboxamidine, which was synthesized in two steps and readily upscaled to gram amounts It exhibited excellent performance in solution-phase reactions, rapidly converting a set of representative aliphatic primary and unhindered secondary amines as well as aniline into the corresponding bis(tert-butoxycarbonyl)-protected guanidines. To enable a direct assessment of the reactivity of guanidinylation reagents, conversions were performed in deuterated solvents (d₇-DMF or d₈-THF), allowing for continuous anal. of the reaction mixtures by ¹H and ¹³C NMR. Likewise, 1H-triazole-1-[N,N’-bis(tert-butoxycarbonyl)]carboxamidine proved to be a versatile reagent in solid-phase conversions, for example, a resin-bound test peptide (KFFKFFK) was fully guanidinylated in only 2 h by using 2 equiv of the reagent per free amino group. Also, 1H-triazole-1-[N,N’-bis(tert-butoxycarbonyl)]carboxamidine proved capable of completely guanidinylating more sterically hindered N-terminal residues (e.g., N-Me amino acids or a peptoid) in resin-bound peptides. Its superior reactivity and stability demonstrated under heating conditions make 1H-triazole-1-[N,N’-bis(tert-butoxycarbonyl)]carboxamidine a valuable guanidinylation reagent both in solution- and solid-phase synthesis.

Journal of Organic Chemistry published new progress about 71989-31-6. 71989-31-6 belongs to catalysis-chemistry, auxiliary class Amino acide derivatives,pyrrolidine, name is Fmoc-Pro-OH, and the molecular formula is C17H16O2, Related Products of catalysis-chemistry.

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

Guzelj, Samo published the artcileDiscovery of Desmuramylpeptide NOD2 Agonists with Single-Digit Nanomolar Potency, Synthetic Route of 1772-76-5, the publication is ACS Medicinal Chemistry Letters (2022), 13(8), 1270-1277, database is CAplus and MEDLINE.

The innate immune receptor nucleotide-binding oligomerization-domain-containing protein 2 (NOD2) represents an important target for the development of structurally defined small mol. immunomodulatory compounds that have great potential to be used either as vaccine adjuvants or as general immunostimulatory agents. We report here the investigation of the structure-activity relationship of a series of novel desmuramylpeptide NOD2 agonists. Extensive exploration of chem. space culminated in the discovery of a lipophilic adamantane-moiety-featuring compound 40, the first single-digit nanomolar and the most potent NOD2 agonist in its structural class to date. Moreover, 40 acted synergistically with lipopolysaccharide and interferon-γ to induce the production of cytokines in human peripheral blood mononuclear cells and enhance their nonspecific cytotoxic activity against K562 cancer cells. These findings provide initial insight into its immunostimulatory potential, especially when used in combination with other immunopotentiators.

ACS 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 C9H7NO4, Synthetic Route of 1772-76-5.

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