Month: January 2023

DNA-cellulose: an economical, fully recyclable and highly effective chiral biomaterial for asymmetric catalysis was written by Benedetti, Erica;Duchemin, Nicolas;Bethge, Lucas;Vonhoff, Stefan;Klussmann, Sven;Vasseur, Jean-Jacques;Cossy, Janine;Smietana, Michael;Arseniyadis, Stellios. And the article was included in Chemical Communications (Cambridge, United Kingdom) in 2015.Category: imidazoles-derivatives This article mentions the following:

The challenge in DNA-based asym. catalysis is to perform a reaction in the vicinity of the helix by incorporating a small-mol. catalyst anchored to the DNA in a covalent, dative, or non-covalent yet stable fashion in order to ensure high levels of enantio-discrimination. Here, we report the first generation of a DNA-based catalyst bound to a cellulose matrix. The chiral biomaterial is com. available, trivial to use, fully recyclable and produces high levels of enantioselectivity in various Cu(II)-catalyzed asym. reactions including Friedel-Crafts alkylations and Michael additions A single-pass, continuous-flow process is also reported affording fast conversions and high enantioselectivities at low catalyst loadings thus offering a new benchmark in the field of DNA-based asym. catalysis. In the experiment, the researchers used many compounds, for example, 1-(1-Methyl-1H-imidazol-2-yl)ethanone (cas: 85692-37-1Category: imidazoles-derivatives).

1-(1-Methyl-1H-imidazol-2-yl)ethanone (cas: 85692-37-1) belongs to imidazole derivatives. 1H-imidazole is an imidazole tautomer which has the migrating hydrogen at position 1. It is a conjugate base of an imidazolium cation. It is a conjugate acid of an imidazolide. It is a tautomer of a 4H-imidazole. Imidazole based anticancer drug find applications in cancer chemotherapy. It is used as buffer component for purification of the histidine tagged recombinant proteins in immobilized metal-affinity chromatography (IMAC).Category: imidazoles-derivatives

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Enantioselective Mukaiyama-Michael Reaction Catalyzed by a Chiral Rhodium Complex Based on Pinene-Modified Pyridine Ligands was written by Gong, Jun;Wan, Qian;Kang, Qiang. And the article was included in Chemistry – An Asian Journal in 2018.Name: 1-(1-Methyl-1H-imidazol-2-yl)ethanone This article mentions the following:

The rhodium complex Λ-Rh1 containing chiral pinene-modified pyridine ligands was prepared through a two-step synthetic procedure; it exhibited excellent reactivity and enantiocontrol toward the enantioselective Mukaiyama-Michael reaction of α,β-unsaturated 2-acyl imidazoles with silyl enol ethers, affording enantioenriched 1,5-dicarbonyl compounds such as I [R = n-Bu, SEt, 4-FC₆H₄, etc.; R¹ = i-Pr, Me; R² = cyclopropyl, 2-thienyl, 4O₂NC₆H₄, etc.] in good yields (up to 99 %) with excellent enantioselectivities (up to 99 % ee). In the experiment, the researchers used many compounds, for example, 1-(1-Methyl-1H-imidazol-2-yl)ethanone (cas: 85692-37-1Name: 1-(1-Methyl-1H-imidazol-2-yl)ethanone).

1-(1-Methyl-1H-imidazol-2-yl)ethanone (cas: 85692-37-1) belongs to imidazole derivatives. Imidazole derivatives generally have good solubility in protic solvents. Simple imidazole derivatives, such as 1H-imidazole, 2-methyl-1H-imidazole, and 1,2-dimethylimidazole, have very high solubility in water. The pharmacophore of imidazole exists in bioactive compounds including amino acids, plant growth regulators and therapeutic agents.n increase of the alkyl chain length of the alcohols. Name: 1-(1-Methyl-1H-imidazol-2-yl)ethanone

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Impact of substituents attached to N-heterocyclic carbenes on the catalytic activity of copper complexes in the reduction of carbonyl compounds with triethoxysilane was written by Peng, Jiajian;Chen, Lingzhen;Xu, Zheng;Hu, Yingqian;Li, Jiayun;Bai, Ying;Qiu, Huayu;Lai, Guoqiao. And the article was included in Chinese Journal of Chemistry in 2009.Synthetic Route of C9H15F6N2P This article mentions the following:

By using functionalized imidazolium salts such as 1-allyl-3-alkylimidazolium or 1-alkyl-3-vinylimidazolium salts as carbene ligand precursors, the reduction of aryl ketones with triethoxysilane catalyzed by copper salt/imidazolium salt/KO-tert-Bu systems was described. The functional substituents attached to the N-heterocyclic carbene serve to enhance the catalytic activity. Different copper salts also have an effect on the catalytic activity, with copper(II) acetate monohydrate being superior to copper(I) chloride. In the experiment, the researchers used many compounds, for example, 1-Butyl-3-vinyl-1H-imidazol-3-ium hexafluorophosphate(V) (cas: 915358-85-9Synthetic Route of C9H15F6N2P).

1-Butyl-3-vinyl-1H-imidazol-3-ium hexafluorophosphate(V) (cas: 915358-85-9) belongs to imidazole derivatives. Many natural products, especially alkaloids, contain the imidazole ring. These imidazoles share the 1,3-C3N2 ring but feature varied substituents. Many drugs contain an imidazole ring, such as certain antifungal drugs, the nitroimidazole series of antibiotics, and the sedative midazolam.Synthetic Route of C9H15F6N2P

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Amphiphilic Pd^II-NHC Complexes on 1,3-Alternate p-tert-Butylthiacalix[4]arene Platform: Synthesis and Catalytic Activities in Coupling and Hydrogenation Reactions was written by Burilov, Vladimir A.;Gafiatullin, Bulat Kh.;Mironova, Diana A.;Sultanova, Elza D.;Evtugyn, Vladimir G.;Osin, Yuri N.;Islamov, Daut R.;Usachev, Konstantin S.;Solovieva, Svetlana E.;Antipin, Igor S.. And the article was included in European Journal of Organic Chemistry in 2020.Electric Literature of C8H8N2 This article mentions the following:

Herein the authors report the first example of amphiphilic Pd^II-NHC complexes on the thiacalix[4]arene backbone in 1,3-alternate configuration. Relative catalytic activity of synthesized Pd^II-NHC complexes in Suzuki-Miyaura coupling of haloarenes with phenylboronic acid was studied. A combination of micellar and metallocomplex catalysis was observed in Suzuki-Miyaura coupling upon going from pure DMF to water/DMF 3:1: the 2-fold increase of conversion of 4-bromoanisole unlike pure DMF was found. Interesting feature was found using chloroarene in DMF/water: the reaction selectivity changed from heterocoupling to homo coupling of phenylboronic acid. Pd^II-NHC complexes demonstrated a high activity in model hydrogenation reaction of p-nitrophenol using sodium borohydride. The most lipophilic Pd^II-NHC complex is most active, which can be attributed with addnl. p-nitrophenol preconcentration in the aggregates due to larger hydrophobic capacity of macrocycle. In the experiment, the researchers used many compounds, for example, 1-Methylbenzimidazole (cas: 1632-83-3Electric Literature of C8H8N2).

1-Methylbenzimidazole (cas: 1632-83-3) belongs to imidazole derivatives. Many natural products, especially alkaloids, contain the imidazole ring. These imidazoles share the 1,3-C3N2 ring but feature varied substituents. Imidazole based anticancer drug find applications in cancer chemotherapy. It is used as buffer component for purification of the histidine tagged recombinant proteins in immobilized metal-affinity chromatography (IMAC).Electric Literature of C8H8N2

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Aggregation of sodium dodecylbenzene sulfonate: Weak molecular interactions modulated by imidazolium cation of short alkyl chain length was written by Agudelo, Alvaro Javier Patino;Ferreira, Guilherme Max Dias;Ferreira, Gabriel Max Dias;Coelho, Yara Luiza;Hudson, Eliara Acipreste;Pires, Ana Clarissa dos Santos;Mendes da Silva, Luis Henrique. And the article was included in Colloids and Surfaces, A: Physicochemical and Engineering Aspects in 2020.Electric Literature of C4H7ClN2 This article mentions the following:

Ionic liquids (ILs) can modify cooperative process in aqueous solutions to a large extent, including anionic surfactant aggregation. Here, the micellization of sodium dodecylbenzene sulfonate (SDBS) was evaluated in low concentrations of 1-alkyl-3-methylimidazolium chloride (C_nmimCl, n = 0, 2, and 4) aqueous solutions through fluorescence spectroscopy, isothermal titration calorimetry, dynamic light scattering, and conductometry. The thermodn. stability of SDBS aggregates strongly depended on the IL structure and concentration, following the order C₄mim⁺ > C₀mim⁺ ≈ C₂mim⁺. At 1.0 mmol L^-1 of the ILs, the increase of the hydrophobicity of the imidazolium cation decreased the enthalpic favorableness, changing ΔH^omic from -3.75 ± 0.07 kJ mol^-1, for C₀mim⁺, to -2.69 ± 0.01 kJ mol^-1, for C₄mim⁺. On the other hand, the entropic feasibility showed an opposite trend, i.e., the higher hydrophobicity of C₄mim⁺ overcame the kosmotropic effect of IL cations in the bulks. We suggested that the imidazolium cations interact with the SDBS monomers on the micellar surface, mainly through hydrophobic, π-π, and electrostatic interactions for C₄mim⁺ and C₂mim⁺, and through electrostatic interactions and hydrogen bonds for C₀mim⁺. In the experiment, the researchers used many compounds, for example, 1-Methyl-1H-imidazol-3-ium chloride (cas: 35487-17-3Electric Literature of C4H7ClN2).

1-Methyl-1H-imidazol-3-ium chloride (cas: 35487-17-3) belongs to imidazole derivatives. 1H-imidazole is an imidazole tautomer which has the migrating hydrogen at position 1. It is a conjugate base of an imidazolium cation. It is a conjugate acid of an imidazolide. It is a tautomer of a 4H-imidazole. The pharmacophore of imidazole exists in bioactive compounds including amino acids, plant growth regulators and therapeutic agents.n increase of the alkyl chain length of the alcohols. Electric Literature of C4H7ClN2

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Understanding Cellulose Dissolution: Energetics of Interactions of Ionic Liquids and Cellobiose Revealed by Solution Microcalorimetry was written by Nunes de Oliveira, Heitor Fernando;Rinaldi, Roberto. And the article was included in ChemSusChem in 2015.Application In Synthesis of 1-Methyl-1H-imidazol-3-ium chloride This article mentions the following:

In this report, the interactions between fifteen selected ionic liquids (ILs) and cellobiose (CB) were examined by high-precision solution microcalorimetry. The heat of mixing (Δ_mixH) of CB and ILs, or CB and IL/mol. solvent (MS) solutions, provides the first ever-published measure of the affinity of CB with ILs. Most importantly, we found that there is a very good correlation between the nature of the results found for Δ_mixH_(CB) and the solubility behavior of cellulose. This correlation suggests that Δ_mixH_(CB) offers a good estimate of the enthalpy of dissolution of cellulose even in solvents in which cellulose is insoluble Therefore, the current findings open up new horizons for unravelling the intricacies of the thermodn. factors accounting for the spontaneity of cellulose dissolution in ILs or IL/MS solutions In the experiment, the researchers used many compounds, for example, 1-Methyl-1H-imidazol-3-ium chloride (cas: 35487-17-3Application In Synthesis of 1-Methyl-1H-imidazol-3-ium chloride).

1-Methyl-1H-imidazol-3-ium chloride (cas: 35487-17-3) belongs to imidazole derivatives. Imidazole derivatives generally have good solubility in protic solvents. Simple imidazole derivatives, such as 1H-imidazole, 2-methyl-1H-imidazole, and 1,2-dimethylimidazole, have very high solubility in water. This ring system is present in important biological building blocks, such as histidine and the related hormone histamine.Application In Synthesis of 1-Methyl-1H-imidazol-3-ium chloride

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Acylation of benzimidazole by the Regel-Buechel method. 2. Deacylation and dissociation of 1-methyl-3-acyl-2-(1-methyl-2-benzimidazolyl)benzimidazolin-4-ones was written by Khristich, B. I.;Bondarenko, E. V.. And the article was included in Khimiya Geterotsiklicheskikh Soedinenii in 1987.Application of 3012-80-4 This article mentions the following:

1-Methyl-3-acyl-2-(1-methylbenzimidazol-2-yl)-2-benzimidazolines with an excess of acyl halide are transformed to unstable 1-methyl-3-acyl-2-(1-methyl-3-acyl-2-benzimidazolin-2-yl)benzimidazolium chlorides, which undergo intramol. oxidation-reduction-decomposition to give 1,1′-dimethyl-2,2′-bibenzimidazolyl and aldehyde, and dissociates at the C-C bond connecting the benzimidazole and benzimidazoline fragments to a carbene-ylide and 1-methyl-3-acylbenzimidazolium chloride. In the experiment, the researchers used many compounds, for example, 1-Methyl-1H-benzo[d]imidazole-2-carbaldehyde (cas: 3012-80-4Application of 3012-80-4).

1-Methyl-1H-benzo[d]imidazole-2-carbaldehyde (cas: 3012-80-4) belongs to imidazole derivatives. Imidazole is a heterocyclic compound with a five-membered planar ring. It is amphoteric and highly polar. The pharmacophore of imidazole exists in bioactive compounds including amino acids, plant growth regulators and therapeutic agents.n increase of the alkyl chain length of the alcohols. Application of 3012-80-4

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Quantum state-resolved molecular scattering of NO (²Π_1/2) at the gas-[C_nmim][Tf₂N] room temperature ionic liquid interface: Dependence on alkyl chain length, collision energy, and temperature was written by Zutz, Amelia;Nesbitt, David J.. And the article was included in AIP Advances in 2016.Name: 3-Dodecyl-1-methyl-1H-imidazol-3-ium bis((trifluoromethyl)sulfonyl)amide This article mentions the following:

Room temperature ionic liquids (RTILs) represent a promising class of chem. tunable, low vapor pressure solvents with myriad kinetic applications that depend sensitively on the nature of gas-mol. interactions at the liquid surface. This paper reports on rovibronically inelastic dynamics at the gas-RTIL interface, colliding supersonically cooled hyperthermal mol. beams of NO (²Π_1/2, N = 0) from 1-alkyl-3-methylimidazolium bis(trifluoromethylsulfonyl)imide (or [C_nmim][Tf₂N]) and probing the scattered NO mols. via laser induced fluorescence (LIF) from the A(²Σ) state. Specifically, inelastic energy transfer into NO rovibrational and electronic degrees of freedom is explored as a function of RTIL alkyl chain length (n), incident collision energy (E_inc) and surface temperature (T_s). At low collision energies (E_inc = 2.7(9) kcal/mol), the scattered NO mols. exhibit a rotational temperature (T_rot) systematically colder than T_s for all chain lengths, which signals the presence of non-equilibrium dynamics in the desorption channel. At high collision energies (E_inc = 20(2) kcal/mol), microscopic branching into trapping/desorption (TD) and impulsive scattering (IS) pathways is clearly evident, with the TD fraction (α) exhibiting a step-like increase between short (n = 2, 4) and long (n = 8, 12, 16) alkyl chains consistent with theor. predictions. For all hydrocarbon chain lengths and RTIL temperature conditions, NO rotational excitation in the IS channel yields hyperthermal albeit Boltzmann-like distributions well described by a “temperature” (T_IS = 900 -1200 K) that decreases systematically with increasing n. Non-adiabatic, collision induced hopping between ground and excited spin-orbit states is found to be independent of RTIL alkyl chain length and yet increase with collision energy. The scattering data confirm previous exptl. reports of an enhanced presence of the alkyl tail at the gas-RTIL interface with increasing n, as well as provide support for theor. predictions of an alkyl length dependent shift between chains oriented parallel vs. perpendicular to the surface normal. (c) 2016 American Institute of Physics. In the experiment, the researchers used many compounds, for example, 3-Dodecyl-1-methyl-1H-imidazol-3-ium bis((trifluoromethyl)sulfonyl)amide (cas: 404001-48-5Name: 3-Dodecyl-1-methyl-1H-imidazol-3-ium bis((trifluoromethyl)sulfonyl)amide).

3-Dodecyl-1-methyl-1H-imidazol-3-ium bis((trifluoromethyl)sulfonyl)amide (cas: 404001-48-5) belongs to imidazole derivatives. Many natural products, especially alkaloids, contain the imidazole ring. These imidazoles share the 1,3-C3N2 ring but feature varied substituents. Imidazole also acts as a microtubule destabilizing agents and inhibits topoisomerase and Cytochrome P450 Family 26 Subfamily A Member 1 (CYP26A1) enzymes.Name: 3-Dodecyl-1-methyl-1H-imidazol-3-ium bis((trifluoromethyl)sulfonyl)amide

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Antimicrobial Activity and SAR Study of New Gemini Imidazolium-Based Chlorides was written by Palkowski, Lukasz;Blaszczynski, Jerzy;Skrzypczak, Andrzej;Blaszczak, Jan;Kozakowska, Karolina;Wroblewska, Joanna;Kozuszko, Sylwia;Gospodarek, Eugenia;Krysinski, Jerzy;Slowinski, Roman. And the article was included in Chemical Biology & Drug Design in 2014.Application In Synthesis of 1-Octyl-1H-imidazole This article mentions the following:

A series of seventy new 3,3′-(α,ω-dioxaalkyl)bis[1-(alkyl)imidazolium] chloride derivatives was prepared They were characterized with respect to surface active properties and antimicrobial activity against the following pathogens: Staphylococcus aureus, Enterococcus faecalis, Acinetobacter baumannii, Escherichia coli, Klebsiella pneumoniae, Enterobacter cloacae, Pseudomonas aeruginosa, Candida krusei and Candida albicans. In this article, besides description of the synthesis, the authors characterize a set of features of these compounds, concerning their structure (described by the length of the dioxaalkane spacer and the length of the alkyl substituent in the aromatic ring) and surface active properties (critical micelle concentration, value of surface tension at critical micelle concentration, value of surface excess, mol. area of a single particle, and free energy of adsorption of mol.). Then, the authors present a SAR study for Staphylococcus aureus, as one of the most widespread pathogenic strains, conducted with the help of the Dominance-based Rough Set Approach (DRSA), that involves identification of relevant features and relevant combinations of features being in strong relationship with a high antimicrobial activity of the compounds The SAR study shows, moreover, that the antimicrobial activity is dependent on the type of substituents and their position at the chloride moiety, as well as on the surface active properties of the compounds The synthesis of the target compounds was achieved by a reaction of 1-(alkyl)-1H-imidazole derivatives with 1,5-bis(chloromethoxy)pentane, 1,6-bis(chloromethoxy)hexane, 1,3-bis(chloromethoxy)propane, etc. The title compounds thus formed included 1,1′-[1,2-ethanediylbis(oxymethylene)]bis[3-octyl-1H-imidazolium] dichloride and related substances, such as 1,1′-[1,4-butanediylbis(oxymethylene)]bis[3-octyl-1H-imidazolium] dichloride, [(alkanediyl)bis[(oxy)methylene]]bis[(alkyl)imidazolium] dichloride derivatives (imidazolium chloride dimers). In the experiment, the researchers used many compounds, for example, 1-Octyl-1H-imidazole (cas: 21252-69-7Application In Synthesis of 1-Octyl-1H-imidazole).

1-Octyl-1H-imidazole (cas: 21252-69-7) belongs to imidazole derivatives. Imidazole derivatives generally have good solubility in protic solvents. Simple imidazole derivatives, such as 1H-imidazole, 2-methyl-1H-imidazole, and 1,2-dimethylimidazole, have very high solubility in water. Many drugs contain an imidazole ring, such as certain antifungal drugs, the nitroimidazole series of antibiotics, and the sedative midazolam.Application In Synthesis of 1-Octyl-1H-imidazole

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Protic Ionic Liquid as Reagent, Catalyst, and Solvent: 1-Methylimidazolium Thiocyanate was written by Andreev, Ivan A.;Ratmanova, Nina K.;Augustin, Andre U.;Ivanova, Olga A.;Levina, Irina I.;Khrustalev, Victor N.;Werz, Daniel B.;Trushkov, Igor V.. And the article was included in Angewandte Chemie, International Edition in 2021.Application of 35487-17-3 This article mentions the following:

We propose a new concept of the triple role of protic ionic liquids with nucleophilic anions: (a) a regenerable solvent, (b) a Broensted acid inducing diverse transformations via general acid catalysis, and (c) a source of a nucleophile. The efficiency of this strategy was demonstrated using thiocyanate-based protic ionic liquids for the ring-opening of donor-acceptor cyclopropanes. A wide variety of activated cyclopropanes were found to react with 1-methylimidazolium thiocyanate under mild metal-free conditions via unusual nitrogen attack of the ambident thiocyanate ion on the electrophilic center of the three-membered ring affording pyrrolidine-2-thiones bearing donor and acceptor substituents at the C(5) and C(3) atoms, resp., in a single time-efficient step [e.g., I → II (81%)]. The ability of 1-methylimidazolium thiocyanate to serve as a triplex reagent was exemplarily illustrated by (4+2)-annulation with 1-acyl-2-(2-hydroxyphenyl)cyclopropane, epoxide ring-opening and other organic transformations. Safety: ammonia evolution in cation metathesis reactions → carry out in fume hood. In the experiment, the researchers used many compounds, for example, 1-Methyl-1H-imidazol-3-ium chloride (cas: 35487-17-3Application of 35487-17-3).

1-Methyl-1H-imidazol-3-ium chloride (cas: 35487-17-3) belongs to imidazole derivatives. Among the different heterocyclic compounds, imidazole is better known due to its broad range of chemical and biological properties. Imidazole has become an important synthon in the development of new drugs. Imidazole also acts as a microtubule destabilizing agents and inhibits topoisomerase and Cytochrome P450 Family 26 Subfamily A Member 1 (CYP26A1) enzymes.Application of 35487-17-3

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem