Tag: 200-300

Carbonylative C-C Bond Activation of Aminocyclopropanes Using a Temporary Directing Group Strategy was written by Wang, Gang-Wei;Sokolova, Olga O.;Young, Tom. A.;Christodoulou, Ektor M. S.;Butts, Craig P.;Bower, John F.. And the article was included in Journal of the American Chemical Society in 2020.Reference of 2387-23-7 This article mentions the following:

Temporary directing groups (TDGs) underpin a range of C-C bond activation methodologies; however, the use of TDGs for the regiocontrolled activation of cyclopropane C-C bonds is underdeveloped. In this report, we show how an unusual ring contraction process can be harnessed for TDG-based carbonylative C-C bond activations of cyclopropanes. The method involves the transient installation of an isocyanate-derived TDG, rather than relying on carbonyl condensation events as used in previous TDG-enabled C-C bond activations. For example, carbonylative ring expansion and contraction of nonracemic cyclopropylurea I yielded nonracemic lactam II. The carbonylative C-C activation reaction was used in tandem with Pictet-Spengler, intramol. Diels-Alder, and alkene-alkyne coupling reactions to yield fused lactams such as III, IV, and V. In the experiment, the researchers used many compounds, for example, 1,3-Dicyclohexylurea (cas: 2387-23-7Reference of 2387-23-7).

1,3-Dicyclohexylurea (cas: 2387-23-7) belongs to amides. The amide group is called a peptide bond when it is part of the main chain of a protein, and an isopeptide bond when it occurs in a side chain, such as in the amino acids asparagine and glutamine. Ionic, or saltlike, amides are strongly alkaline compounds ordinarily made by treating ammonia, an amine, or a covalent amide with a reactive metal such as sodium.Reference of 2387-23-7

Referemce:
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Occurrences of Tire Rubber-Derived Contaminants in Cold-Climate Urban Runoff was written by Challis, J. K.;Popick, H.;Prajapati, S.;Harder, P.;Giesy, J. P.;McPhedran, K.;Brinkmann, M.. And the article was included in Environmental Science & Technology Letters in 2021.Application of 2387-23-7 This article mentions the following:

Recent findings that 2-anilo-5-[(4-methylpentan-2-yl)amino]cyclohexa-2,5-diene-1,4-dione (6PPD-quinone), the transformation product of a common tire rubber antioxidant, is acutely toxic in stormwater-impacted streams has highlighted the need for a better understanding of contaminants in urban runoff. This study represents one of the first reports of 6PPD-quinone and other tire rubber-derived compounds in stormwater and snowmelt of a cold-climate Canadian city (Saskatoon, 2019-2020). Semiquantification of the five target compounds, N,N′-diphenylguanidine (DPG), N,N-dicyclohexylmethylamine (DCA), N,N′-dicyclohexylurea (DCU), 1-cyclohexyl-3-phenylurea (CPU), and 6PPD-quinone, revealed DPG was most abundant, with average concentrations of 60 μg L^-1 in stormwater and 1 μg L^-1 in snowmelt. Maximum observed concentrations of DPG were greater than 300 μg L^-1, equivalent to loadings of 15 kg from a single rain event. These concentrations of DPG represent some of the highest reported in urban runoff globally. 6PPD-Quinone was detected in 57% (12/21) of stormwater samples with a mean concentration of approx. 600 ng L-1 (2019) and greater than 80% (28/31) of snowmelt samples with mean concentrations of 80-370 ng L-1 (2019 and 2020). Concentrations of 6PPD-quinone exceeded the acute LC₅₀ for coho salmon (0.8-1.2 μg L^-1) in greater than 20% of stormwater samples. Mass loadings of all target chems. correlated well with roads and residential land-use area. In the experiment, the researchers used many compounds, for example, 1,3-Dicyclohexylurea (cas: 2387-23-7Application of 2387-23-7).

1,3-Dicyclohexylurea (cas: 2387-23-7) belongs to amides. Because of the greater electronegativity of oxygen, the carbonyl (C=O) is a stronger dipole than the N–C dipole. The presence of a C=O dipole and, to a lesser extent a N–C dipole, allows amides to act as H-bond acceptors. Amides are stable compounds. The lower-melting members (such as acetamide) can be readily purified by fractional distillation. Most amides are solids which have low solubilities in water.Application of 2387-23-7

Referemce:
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Parallel synthesis of 1,2,3-thiadiazoles employing a “Catch and Release” strategy was written by Hu, Yonghan;Baudart, Sylvie;Porco, John A. Jr.. And the article was included in Journal of Organic Chemistry in 1999.COA of Formula: C9H10BrNO2 This article mentions the following:

A very efficient hybrid solution-/solid phase sequence for the synthesis of 1,2,3-thiadiazoles employing “resin capture” of ketones without the need for chromatog. was developed. Cyclative cleavage of resin-bound sulfonylhydrazones was accomplished using thionyl chloride to afford 1,2,3-thiadiazoles. Stille coupling of resin-bound intermediates was also demonstrated. In the experiment, the researchers used many compounds, for example, 4-Bromo-N-methoxy-N-methylbenzamide (cas: 192436-83-2COA of Formula: C9H10BrNO2).

4-Bromo-N-methoxy-N-methylbenzamide (cas: 192436-83-2) belongs to amides. Amides are pervasive in nature and technology. Proteins and important plastics like Nylons, Aramid, Twaron, and Kevlar are polymers whose units are connected by amide groups (polyamides); these linkages are easily formed, confer structural rigidity, and resist hydrolysis. Amides are not in general accessible by the direct condensation of amines with carboxylic acids for two reasons: first, both components are readily deactivated by a transfer of a proton from the acid to the amine and second, the hydroxy unit on the carbonyl of the acid is a relatively poor leaving group. Nevertheless, the formation of five- and six-membered rings is often surprisingly simple provided that other factors can be brought into play to assist in the condensation.COA of Formula: C9H10BrNO2

Referemce:
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Heterogeneous Pd-Catalyzed Efficient Synthesis of Imidazolones via Dehydrogenative Condensation between Ureas and 1,2-Diols was written by Arango-Daza, Juan Camilo;Lluna-Galan, Carles;Izquierdo-Aranda, Luis;Cabrero-Antonino, Jose R.;Adam, Rosa. And the article was included in ACS Catalysis in 2022.Application of 2387-23-7 This article mentions the following:

A heterogeneously catalyzed protocol for the acceptorless dehydrogenative condensation between N,N’-disubstituted ureas and 1,2-diols to afford imidazolones was developed. Palladium nanoaggregates stabilized onto an alumina matrix with suitable acidic properties, namely, [Pd/Al2O3], was designed and successfully applied as efficient and reusable heterogeneous nanocatalyst for this relevant transformation. The methodol. developed showed its wide applicability through the synthesis of more than 25 imidazolones with moderate to good yields, reaching a turnover number (TON) of up to 19444 and a initial turnover frequency (TOF₀) > 290 h^-1. The active nanostructured catalyst was fully characterized [X-ray diffraction (XRD), high-resolution transmission electron microscopy (HR-TEM), high-resolution scanning transmission electron microscopy (HR-STEM), energy-dispersive X-ray (EDX), Raman spectroscopy, temperature-programmed reduction (TPR), temperature-programmed desorption (TPD)-NH3, TPD-CO2, XPS, Brunauer-Emmett-Teller (BET) area], and mechanistic studies were performed. Moreover, other related Pd-based nanomaterials composed of different acidic or basic inorganic supports were synthesized and extensively compared in this reaction. These studies revealed that the presence of Pd nanoparticles with a wide range of sizes (average particle size 2.8 nm) over a metal oxide support with a high d. of acid sites is a key point for the good activity of the material, γ-Al₂O₃ being the optimum support. Furthermore, a Pd-Zn cooperation effect was described for the dehydrogenative condensation of unactivated 1,2-diols, including ethylene glycol, with ureas. Two Pd-Zn bimetallic materials ([Pd/ZnO] and [Pd(5%)-Zn(5%)/A_l2O₃]) were also designed and characterized properly. These materials, as well as the [Pd/Al₂O₃] system in combination with catalytic amounts of ZnO, showed good activity and selectivity in the acceptorless dehydrogenative condensation between ureas and unactivated 1,2-diols. The heterogeneous nature of all of the described catalytic systems was demonstrated, and the reusability of the catalysts was proven. In the experiment, the researchers used many compounds, for example, 1,3-Dicyclohexylurea (cas: 2387-23-7Application of 2387-23-7).

1,3-Dicyclohexylurea (cas: 2387-23-7) belongs to amides. Amides can be viewed as a derivative of a carboxylic acid RC(=O)OH with the hydroxyl group –OH replaced by an amine group −NR′R″; or, equivalently, an acyl (alkanoyl) group RC(=O)− joined to an amine group. Amides can be freed from solvent or water by drying below their melting points. These purifications can also be used for sulfonamides and acid hydrazides.Application of 2387-23-7

Referemce:
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Collection of ion-trap mass spectra of sulfonylurea pyrolysis products was written by Galletti, Guido C.;Dinelli, Giovanni;Chiavari, Giuseppe. And the article was included in Journal of Mass Spectrometry in 1995.Synthetic Route of C8H10ClNO3S This article mentions the following:

The pyrograms of 14 sulfonylureas, i.e. herbicides characterized by high biol. activity and low application dose are discussed and the mass spectra of over 30 relevant pyrolysis products as obtained with a heated filament pyrolyzer interfaces to a capillary gas chromatograph/ion-trap detector mass spectrometer are presented. Such a data compilation is useful for diagnostic purposes for both intact sulfonylureas and their metabolites after determination in soil, because metabolites and pyrolysis products are often identical and most of their mass spectra are lacking in com. available mass spectral libraries. The performance of the ion-trap detector based on the quality of the mass spectra is briefly discussed. In the experiment, the researchers used many compounds, for example, 2-(2-Chloroethoxy)benzenesulfonamide (cas: 82097-01-6Synthetic Route of C8H10ClNO3S).

2-(2-Chloroethoxy)benzenesulfonamide (cas: 82097-01-6) belongs to amides. The solubilities of amides and esters are roughly comparable. Typically amides are less soluble than comparable amines and carboxylic acids since these compounds can both donate and accept hydrogen bonds. Tertiary amides, with the important exception of N,N-dimethylformamide, exhibit low solubility in water. Amides can be recrystallised from large quantities of water, ethanol, ethanol/ether, aqueous ethanol, chloroform/toluene, chloroform or acetic acid. The likely impurities are the parent acids or the alkyl esters from which they have been made. The former can be removed by thorough washing with aqueous ammonia followed by recrystallisation, whereas elimination of the latter is by trituration or recrystallisation from an organic solvent.Synthetic Route of C8H10ClNO3S

Referemce:
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Establishment of an effective activated peroxide system for low-temperature cotton bleaching using synthesized tetramido macrocyclic iron complex was written by Yu, Deyou;Wu, Minghua;Lin, Junxiong. And the article was included in Fibers and Polymers in 2017.Application of 10543-57-4 This article mentions the following:

In this study, the tetramido macrocyclic iron complex (Fe-TAML) was successfully synthesized, and then it was characterized using ¹H NMR, electrospray ionization mass spectrometry (EIS-MS) and elemental anal. An activated peroxide system was established for low-temperature bleaching of cotton by combining the synthesized catalyst (Fe-TAML) with hydrogen peroxide. Exptl. results showed that the Fe-TAML/H₂O₂ bleaching system exhibited effective bleaching performance in the use of 2 μM Fe-TAML, 20 g/l H₂O₂, 1 g/l NaHCO₃, 2 g/l scouring agent and 2 g/l wetting agent at 60 °C for 60 min. In comparison with the conventional bleaching system, the Fe-TAML/H₂O₂ system provided bleached cotton with a superior degree of whiteness, higher tensile strength and acceptable water absorbency. The application of Fe-TAML was expanded and the activated peroxide system may provide a green approach for the cotton bleaching. In the experiment, the researchers used many compounds, for example, N,N-(Ethane-1,2-diyl)bis(N-acetylacetamide) (cas: 10543-57-4Application of 10543-57-4).

N,N-(Ethane-1,2-diyl)bis(N-acetylacetamide) (cas: 10543-57-4) belongs to amides. Amides can be viewed as a derivative of a carboxylic acid RC(=O)OH with the hydroxyl group –OH replaced by an amine group −NR′R″; or, equivalently, an acyl (alkanoyl) group RC(=O)− joined to an amine group. Amides can be freed from solvent or water by drying below their melting points. These purifications can also be used for sulfonamides and acid hydrazides.Application of 10543-57-4

Referemce:
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Hydrophobic Pockets of HPMC Enable Extremely Short Reaction Times in Water was written by Petkova, Desislava;Borlinghaus, Niginia;Sharma, Sudripet;Kaschel, Johannes;Lindner, Tanja;Klee, Johanna;Jolit, Anais;Haller, Vanessa;Heitz, Stephanie;Britze, Katarina;Dietrich, Justin;Braje, Wilfried M.;Handa, Sachin. And the article was included in ACS Sustainable Chemistry & Engineering in 2020.COA of Formula: C9H10BrNO2 This article mentions the following:

A methodol. for formation of ligated ultrasmall in-situ generated Pd nanoparticles in the hydrophobic pockets of benign cellulose derivative hydroxypropyl methylcellulose (HPMC) for chem. reactions to proceed very fast in water under mild reaction conditions was reported. Unprecedented short reaction times were exemplified for the Buchwald-Hartwig amination reaction of aryl bromides and aryl amines using in-situ generated Pd nanoparticles in aqueous HMPC solution to afford substituted aryl amines RNHR¹ [R = 1-naphthyl, 3-MeC₆H₄, 2-MeOC₆H₄, etc.; R¹ = Ph, 4-MeC₆H₄, 1-naphthyl, etc.]. In addition, very short reaction times were also demonstrated for the peptide coupling of carboxylic acids and amines using in-situ generated Pd nanoparticles in aqueous HMPC solution to afford aryl amides R²C(O)NR³R⁴ [R² = Bn, 4-ClC₆H₄, 4-BrC₆H₄, etc.; R³ = OMe, n-hexyl, 3,5-(Me)₂C₆H₃, etc.; R⁴ = H, Me, etc.]. In the experiment, the researchers used many compounds, for example, 4-Bromo-N-methoxy-N-methylbenzamide (cas: 192436-83-2COA of Formula: C9H10BrNO2).

4-Bromo-N-methoxy-N-methylbenzamide (cas: 192436-83-2) belongs to amides. In primary and secondary amides, the presence of N–H dipoles allows amides to function as H-bond donors as well. Thus amides can participate in hydrogen bonding with water and other protic solvents; the oxygen atom can accept hydrogen bonds from water and the N–H hydrogen atoms can donate H-bonds. Amides are stable compounds. The lower-melting members (such as acetamide) can be readily purified by fractional distillation. Most amides are solids which have low solubilities in water.COA of Formula: C9H10BrNO2

Referemce:
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Hemin-catalyzed biomimetic oxidative phenol-indole [3 + 2] reactions in aqueous media was written by Fu, Yu;Yu, Qile;Zhang, Yulong;Gao, Zhonghong;Wu, Yuzhou;Zhong, Fangrui. And the article was included in Organic & Biomolecular Chemistry in 2019.Reference of 1146-43-6 This article mentions the following:

A hemin/H₂O₂ catalytic system for oxidative phenol-indole [3 + 2] coupling in aqueous solution was developed, enabling benign synthesis of valuable benzofuroindolines under sustainable conditions. Mechanistic studies revealed the dual role of iron porphyrin responsible for both phenol oxidation and Lewis acid activation, which differs from the well-explored chem. of hemin in carbene and nitrene insertion reactions. A preliminary experiment with cytochrome c showed that the turnover of iron porphyrin was amenable for a macromol. setting with remarkable efficiency (∼13,300 TON). In the experiment, the researchers used many compounds, for example, N-(4-Hydroxyphenyl)-4-methylbenzenesulfonamide (cas: 1146-43-6Reference of 1146-43-6).

N-(4-Hydroxyphenyl)-4-methylbenzenesulfonamide (cas: 1146-43-6) belongs to amides. Compared to amines, amides are very weak bases and do not have clearly defined acid–base properties in water. On the other hand, amides are much stronger bases than esters, aldehydes, and ketones. Amides are not in general accessible by the direct condensation of amines with carboxylic acids for two reasons: first, both components are readily deactivated by a transfer of a proton from the acid to the amine and second, the hydroxy unit on the carbonyl of the acid is a relatively poor leaving group. Nevertheless, the formation of five- and six-membered rings is often surprisingly simple provided that other factors can be brought into play to assist in the condensation.Reference of 1146-43-6

Referemce:
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Design, synthesis, and biological evaluation of potent thiosemicarbazone based cathepsin L inhibitors was written by Kishore Kumar, G. D.;Chavarria, Gustavo E.;Charlton-Sevcik, Amanda K.;Arispe, Wara M.;MacDonough, Matthew T.;Strecker, Tracy E.;Chen, Shen-En;Siim, Bronwyn G.;Chaplin, David J.;Trawick, Mary Lynn;Pinney, Kevin G.. And the article was included in Bioorganic & Medicinal Chemistry Letters in 2010.COA of Formula: C10H10F3NO2 This article mentions the following:

A small library of 36 functionalized benzophenone thiosemicarbazone analogs was prepared by chem. synthesis and evaluated for their ability to inhibit the cysteine proteases cathepsin L and cathepsin B. The six most active inhibitors of cathepsin L (IC₅₀ < 85 nM) in this series were I (R = 2-F, 3-F₃C, 4-F, 2,3-F₂, 3,5-F₂, 2,3,4,5-F₄). These six analogs were selective for their inhibition of cathepsin L vs. cathepsin B (IC₅₀ > 10,000 nM). The most active analog in the series, thiosemicarbazone I (R = 2-F), also efficiently inhibited cell invasion of the DU-145 human prostate cancer cell line. In the experiment, the researchers used many compounds, for example, N-Methoxy-N-methyl-4-(trifluoromethyl)benzamide (cas: 116332-61-7COA of Formula: C10H10F3NO2).

N-Methoxy-N-methyl-4-(trifluoromethyl)benzamide (cas: 116332-61-7) belongs to amides. The amide group is called a peptide bond when it is part of the main chain of a protein, and an isopeptide bond when it occurs in a side chain, such as in the amino acids asparagine and glutamine. Amides can be freed from solvent or water by drying below their melting points. These purifications can also be used for sulfonamides and acid hydrazides.COA of Formula: C10H10F3NO2

Referemce:
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Molecular encapsulation of berberine and ethidium bromide in anthraquinone-carboxamido-β-cyclodextrin conjugate: supramolecular association with DNA duplex and G-quadruplexes was written by Soundarapandian, Suganthi;Alexander, Aleyamma;Sumohan Pillai, Archana;Enoch, Israel V. M. V.;Yousuf, Sameena. And the article was included in Nucleosides, Nucleotides & Nucleic Acids in 2021.Recommanded Product: 2387-23-7 This article mentions the following:

G-quadruplex DNA in recognized as a potential target for anticancer drugs. In this work, an anthraquinonecarboxamido derivative of β-cyclodextrin (AQCC) is synthesized as a novel DNA binder that further can deliver an addnl. mol. at the target, carrying it in the cavity of modified cyclodextrin. The binding of AQCC with ethidium bromide (EtBr), berberine (Ber), duplex calf-thymus DNA (CT-DNA), quadruplexes, e.g. 5′-AGGGAGGGCGCTGGGAGGAGGG-3′ are studied. The compound acts as a host mol. for the encapsulation of DNA binders viz., EtBr, Ber and enhances their fluorescence due to the encapsulation in its AQCC’s cyclodextrin cavity. The conjugate displays a quenching of fluorescence selectively on the association with CT-DNA and quadruplexes. CT-DNA exhibits dissimilar fluorescence spectra in free- and EtBr-bound forms. In addition, the effect of Ber in binding to the target DNAs is pronounces since the Ber mol. has more affinity to bind to quadruplexes than the duplex. In the experiment, the researchers used many compounds, for example, 1,3-Dicyclohexylurea (cas: 2387-23-7Recommanded Product: 2387-23-7).

1,3-Dicyclohexylurea (cas: 2387-23-7) belongs to amides. The amide group is called a peptide bond when it is part of the main chain of a protein, and an isopeptide bond when it occurs in a side chain, such as in the amino acids asparagine and glutamine. The presence of the amide group –C(=O)N– is generally easily established, at least in small molecules. It can be distinguished from nitro and cyano groups in IR spectra. Amides exhibit a moderately intense νCO band near 1650 cm−1. By 1H NMR spectroscopy, CONHR signals occur at low fields. In X-ray crystallography, the C(=O)N center together with the three immediately adjacent atoms characteristically define a plane.Recommanded Product: 2387-23-7

Referemce:
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics