Ethers-buliding-blocks

Efficient visible light initiated one-pot syntheses of secondary amines from nitro aromatics and benzyl alcohols over Pd@NH₂-UiO-66(Zr) was written by Hao, Mingming;Li, Zhaohui. And the article was included in Applied Catalysis, B: Environmental in 2022.Formula: C8H10O2 This article mentions the following:

Pd@NH₂-UiO-66(Zr), with small-sized Pd nanoparticles encapsulated inside the cavities of NH₂-UiO-66(Zr), was obtained via a double-solvent impregnation followed by a photoreduction process, which shows superior activity for the visible light initiated syntheses of secondary amines from nitro compounds and alcs., via a sequential photocatalytic hydrogenation of nitro compounds/dehydrogenation of alcs., condensation of amines and aldehydes to imines, and the hydrogenation of imines. Simultaneous consumption of photogenerated electrons/holes in the photocatalytic hydrogenation of nitro compounds to amines and dehydrogenation of alcs. to aldehydes promotes the whole reaction. Due to the confinement effect of the cavity and the small-sized Pd nanoparticles, Pd@NH₂-UiO-66(Zr) shows significantly superior performance as compared with Pd/NH₂-UiO-66(Zr), in which larger Pd nanoparticles are deposited on the surface. This study provides an efficient and green strategy for the production of secondary amines and highlights the great potential of using M/MOFs nanocomposites as multifunctional catalysts for light induced one-pot tandem reactions. In the experiment, the researchers used many compounds, for example, (4-Methoxyphenyl)methanol (cas: 105-13-5Formula: C8H10O2).

(4-Methoxyphenyl)methanol (cas: 105-13-5) belongs to ethers. Relative to alcohols, ethers are generally less dense, are less soluble in water, and have lower boiling points. They are relatively unreactive, and as a result they are useful as solvents for fats, oils, waxes, perfumes, resins, dyes, gums, and hydrocarbons. Vapours of certain ethers are used as insecticides, miticides, and fumigants for soil. Ethers are good solvents partly because they are not very reactive. Most ethers can be cleaved, however, by hydrobromic acid (HBr) to give alkyl bromides or by hydroiodic acid (HI) to give alkyl iodides.Formula: C8H10O2

Referemce:
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Design, synthesis, and evaluation of dihydropyranopyrazole derivatives as novel PDE2 inhibitors for the treatment of Alzheimer’s disease was written by Zhou, Yan;Li, Jinjian;Yuan, Han;Su, Rui;Huang, Yue;Huang, Yiyou;Li, Zhe;Wu, Yinuo;Luo, Haibin;Zhang, Chen;Huang, Ling. And the article was included in Molecules in 2021.Reference of 57179-35-8 This article mentions the following:

In this study, (R)-LZ77 was obtained as a hit compound with moderate PDE2 inhibitory activity (IC₅₀ = 261.3 nM) using a high-throughput virtual screening method based on mol. dynamics. Then, 28 dihydropyranopyrazole derivatives I [R¹ = H, CH₃O, Cl; R² = H, CH₃, CH₃O, etc.; R³ = H, CH₃, C₆H₅; R⁴ = H, CH₃O, Cl, etc; R⁵ = NH₂, (CH₃)₂N; n = 1, 2, 3] and II [R⁶ = Cl, CF₃; n = 0, 2, 3] were designed and synthesized as PDE2 inhibitors. Among them, compound (+)-I [R¹ = H; R² = CH₃O; R³ = CH₃; R⁴ = CF₃; R⁵ = NH₂; n = 1] was the most potent PDE2 inhibitor, with an IC₅₀ value of 41.5 nM. The mol. docking of PDE2-(+)-I [R¹ = H; R² = CH₃O; R³ = CH₃; R⁴ = CF₃; R⁵ = NH₂; n = 1] revealed that the 4-(trifluoromethyl)benzyloxyl side chain of the compound enters the H-pocket and forms strong hydrophobic interactions with L770/L809/F862, which improves inhibitory activity. The above results may provide insight for further structural optimization of highly potent PDE2 inhibitors and may lay the foundation for their use in the treatment of AD. In the experiment, the researchers used many compounds, for example, 3-Hydroxy-5-methoxybenzaldehyde (cas: 57179-35-8Reference of 57179-35-8).

3-Hydroxy-5-methoxybenzaldehyde (cas: 57179-35-8) belongs to ethers. Relative to alcohols, ethers are generally less dense, are less soluble in water, and have lower boiling points. They are relatively unreactive. Electron-deficient reagents are also stabilized by ethers. For example, borane (BH3) is a useful reagent for making alcohols. Pure borane exists as its dimer, diborane (B2H6), a toxic gas that is inconvenient and hazardous to use. Borane forms stable complexes with ethers, however, and it is often supplied and used as its liquid complex with tetrahydrofuran (THF).Reference of 57179-35-8

Referemce:
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Poly(ionic liquid)s with branched side chains: polymer design for breaking the conventional record of ionic conductivity was written by Ikeda, Taichi. And the article was included in Polymer Chemistry in 2021.Application In Synthesis of 2-(2-(2-((Tetrahydro-2H-pyran-2-yl)oxy)ethoxy)ethoxy)ethan-1-ol This article mentions the following:

Poly(ionic liquid)s with non-branched, di-branched, and tri-branched side chains were synthesized using cationic glycidyl triazolyl polymers (GTPs). Based on the analyses of these cationic GTPs, the effects of side-chain branching on phys. properties, such as glass transition temperature and ionic conductivity, were discussed. It was confirmed that the ionic conductivity increased with the degree of side-chain branching. Despite being a high-mol.-weight polymer (1.9 x 10⁶ Da), GTP with tri-branched side chains exhibited a high ionic conductivity of 3.6 x 10^-5 M at 25°C under dry conditions, which is higher than the benchmark value of the conventional poly(ionic liquid)s proposed by Shaplov, Marcilla, and Mecerreyes (3.0 x 10^-5 M at 25°C, dry conditions, mol. weight >10⁵ Da). From the anal. based on the electrode polarization model, the higher ionic conductivity of cationic GTPs with branched side chains can be attributed to their higher conducting ion mobility in the polymer matrix. These results indicate that side-chain branching is effective in breaking the conventional limit of ionic conductivity of poly(ionic liquid)s. In the experiment, the researchers used many compounds, for example, 2-(2-(2-((Tetrahydro-2H-pyran-2-yl)oxy)ethoxy)ethoxy)ethan-1-ol (cas: 60221-37-6Application In Synthesis of 2-(2-(2-((Tetrahydro-2H-pyran-2-yl)oxy)ethoxy)ethoxy)ethan-1-ol).

2-(2-(2-((Tetrahydro-2H-pyran-2-yl)oxy)ethoxy)ethoxy)ethan-1-ol (cas: 60221-37-6) belongs to ethers. Relative to alcohols, ethers are generally less dense, are less soluble in water, and have lower boiling points. They are relatively unreactive. Ethers are good solvents partly because they are not very reactive. Most ethers can be cleaved, however, by hydrobromic acid (HBr) to give alkyl bromides or by hydroiodic acid (HI) to give alkyl iodides.Application In Synthesis of 2-(2-(2-((Tetrahydro-2H-pyran-2-yl)oxy)ethoxy)ethoxy)ethan-1-ol

Referemce:
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Inter- and intra-molecular organocatalysis of S_N2 fluorination by crown ether: kinetics and quantum chemical analysis was written by Oh, Young-Ho;Yun, Wonhyuck;Kim, Chul-Hee;Jang, Sung-Woo;Lee, Sung-Sik;Lee, Sungyul;Kim, Dong-Wook. And the article was included in Molecules in 2021.Reference of 3929-47-3 This article mentions the following:

We present the intra- and inter-mol. organocatalysis of S_N2 fluorination using CsF by crown ether to estimate the efficacy of the promoter and to elucidate the reaction mechanism. The yields of intramol. S_N2 fluorination of the veratrole substrates are measured to be very small (<1% in 12 h) in the absence of crown ether promoters, whereas the S_N2 fluorination of the substrate possessing a crown ether unit proceeds to near completion (~99%) in 12 h. We also studied the efficacy of intermol. rate acceleration by an independent promoter 18-crown-6 for comparison. We find that the fluorinating yield of a veratrole substrate (leaving group = -OMs) in the presence of 18-crown-6 follows the almost identical kinetic course as that of intramol. S_N2 fluorination, indicating the mechanistic similarity of intra- and inter-mol. organocatalysis of the crown ether for S_N2 fluorination. The calculated relative Gibbs free energies of activation for these reactions, in which the crown ether units act as Lewis base promoters for S_N2 fluorination, are in excellent agreement with the exptl. measured yields of fluorination. The role of the metal salt CsF is briefly discussed in terms of whether it reacts as a contact ion pair or as a “free” nucleophile F^–. In the experiment, the researchers used many compounds, for example, 3-(3,4-Dimethoxyphenyl)propan-1-ol (cas: 3929-47-3Reference of 3929-47-3).

3-(3,4-Dimethoxyphenyl)propan-1-ol (cas: 3929-47-3) belongs to ethers. Ether is less polar than esters, alcohols or amines because of the oxygen atom that is unable to participate in hydrogen bonding due to the presence of bulky alkyl groups on both sides of the oxygen atom. But ether is more polar than alkenes. Ethers are good solvents partly because they are not very reactive. Most ethers can be cleaved, however, by hydrobromic acid (HBr) to give alkyl bromides or by hydroiodic acid (HI) to give alkyl iodides.Reference of 3929-47-3

Referemce:
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Pentafluoroethylation of Carbonyl Compounds by HFC-125 via the Encapsulation of the K Cation with Glymes was written by Fujihira, Yamato;Hirano, Kazuki;Ono, Makoto;Mimura, Hideyuki;Kagawa, Takumi;Sedgwick, Daniel M.;Fustero, Santos;Shibata, Norio. And the article was included in Journal of Organic Chemistry in 2021.Product Details of 112-49-2 This article mentions the following:

A simple protocol to overcome the explosive pentafluoroethylation of carbonyl compounds by HFC-125 is described. The use of potassium (K) bases with triglyme or tetraglyme as a solvent safely yields the pentafluoroethylation products in good to high yields. The exptl. results suggest that an encapsulation of the K cation by glymes as K(glyme)₂ inhibits the contact between the K cation and the reactive anionic pentafluoroethyl counterion, preventing their transformation into KF and explosive tetrafluoroethylene (TFE). The generation of sterically demanding [K(G3)₂]⁺ and [K(G4)₂]⁺ is an effective way as an unstable pentafluoroethyl anion reservoir. In the experiment, the researchers used many compounds, for example, 2,5,8,11-Tetraoxadodecane (cas: 112-49-2Product Details of 112-49-2).

2,5,8,11-Tetraoxadodecane (cas: 112-49-2) belongs to ethers. Ethers are good solvents partly because they are not very reactive. Most ethers can be cleaved, however, by hydrobromic acid (HBr) to give alkyl bromides or by hydroiodic acid (HI) to give alkyl iodides. At room temperature, ethers are pleasant-smelling colourless liquids. Relative to alcohols, ethers are generally less dense, are less soluble in water, and have lower boiling points. They are relatively unreactive, and as a result they are useful as solvents for fats, oils, waxes, perfumes, resins, dyes, gums, and hydrocarbons. Vapours of certain ethers are used as insecticides, miticides, and fumigants for soil.Product Details of 112-49-2

Referemce:
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Difuran-substituted quinoxalines as a novel class of PI3Kα H1047R mutant inhibitors: Synthesis, biological evaluation and structure-activity relationship was written by Zhang, Ning;Yu, Zhimei;Yang, Xiaohong;Zhou, Yan;Tang, Qing;Hu, Ping;Wang, Jia;Zhang, Shao-Lin;Wang, Ming-Wei;He, Yun. And the article was included in European Journal of Medicinal Chemistry in 2018.Recommanded Product: 365564-07-4 This article mentions the following:

Phosphatidylinositol 3-kinase α (PI3Kα) is the most frequently mutated kinase in human cancers, making it an attractive therapeutic target for cancer treatment. The authors identified a structurally novel PI3Kα H1047R mutant inhibitor Hit-01 (5,7-dichloro-2,3-di(furan-2-yl)quinoxaline) (EC₅₀ = 76.0 μM) through a high-throughput screening campaign. Chem. optimizations enabled the authors to discover compound 7b (6-bromo-7-(2-fluorophenyl)-2,3-di(furan-2-yl)quinoxaline), which strongly inhibited PI3Kα H1047R mutant with an EC₅₀ value of 0.137 μM, over 500-fold more potent than Hit-01. Western blotting anal. suggested that 7b could decrease the phosphorylation level of p-AKT, another proof that 7b inhibited PI3Kα H1047R function. Cell viability assay revealed that 7b inhibited HCT116 cancer cell growth with an IC₅₀ value of 11.23 μM. In addition, 7b was found to arrest cell cycle at G1 phase and induce cell apoptosis via up-regulation of caspase-3, caspase-8 and caspase-9 protein expressions. Collectively, all these data demonstrated that 7b could be a promising lead for the development of structurally novel PI3Kα inhibitors. In the experiment, the researchers used many compounds, for example, 2-(3,5-Dimethoxyphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (cas: 365564-07-4Recommanded Product: 365564-07-4).

2-(3,5-Dimethoxyphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (cas: 365564-07-4) belongs to ethers. Of all the functional groups, ethers are the least reactive ones. Ether bonds are quite stable towards bases, oxidizing agents and reducing agents. Ethyl ether is an excellent solvent for extractions and for a wide variety of chemical reactions. It is also used as a volatile starting fluid for diesel engines and gasoline engines in cold weather. Dimethyl ether is used as a spray propellant and refrigerant. Methyl t-butyl ether (MTBE) is a gasoline additive that boosts the octane number and reduces the amount of nitrogen-oxide pollutants in the exhaust. The ethers of ethylene glycol are used as solvents and plasticizers.Recommanded Product: 365564-07-4

Referemce:
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Structural complexity through multicomponent cycloaddition cascades enabled by dual-purpose, reactivity regenerating 1,2,3-triene equivalents was written by Wender, Paul A.;Fournogerakis, Dennis N.;Jeffreys, Matthew S.;Quiroz, Ryan V.;Inagaki, Fuyuhiko;Pfaffenbach, Magnus. And the article was included in Nature Chemistry in 2014.Safety of 1,4-Dimethoxy-2-butyne This article mentions the following:

Multicomponent reactions allow for more bond-forming events per synthetic operation, enabling more step- and time-economical conversion of simple starting materials to complex and thus value-added targets. These processes invariably require that reactivity be relayed from intermediate to intermediate over several mechanistic steps until a termination event produces the final product. Here, the authors report a multicomponent process in which a novel 1,2,3-butatriene equivalent (TMSBO: TMSCH2C CCH2OH) engages chemospecifically as a two-carbon alkyne component in a metal-catalyzed [5 + 2] cycloaddition with a vinylcyclopropane to produce an intermediate cycloadduct. Under the reaction conditions, this intermediate undergoes a remarkably rapid 1,4-Peterson elimination, producing a reactive four-carbon diene intermediate that is readily intercepted in either a metal-catalyzed or thermal [4 + 2] cycloaddition TMSBO thus serves as an yne-to-diene transmissive reagent coupling two powerful and convergent cycloadditions-the homologous Diels-Alder and Diels-Alder cycloadditions-through a vinylogous Peterson elimination, and enabling flexible access to diverse polycycles. In the experiment, the researchers used many compounds, for example, 1,4-Dimethoxy-2-butyne (cas: 16356-02-8Safety of 1,4-Dimethoxy-2-butyne).

1,4-Dimethoxy-2-butyne (cas: 16356-02-8) belongs to ethers. Ether is less polar than esters, alcohols or amines because of the oxygen atom that is unable to participate in hydrogen bonding due to the presence of bulky alkyl groups on both sides of the oxygen atom. But ether is more polar than alkenes. At room temperature, ethers are pleasant-smelling colourless liquids. Relative to alcohols, ethers are generally less dense, are less soluble in water, and have lower boiling points. They are relatively unreactive, and as a result they are useful as solvents for fats, oils, waxes, perfumes, resins, dyes, gums, and hydrocarbons. Vapours of certain ethers are used as insecticides, miticides, and fumigants for soil.Safety of 1,4-Dimethoxy-2-butyne

Referemce:
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Selective monotetrahydropyranylation of symmetrical diols using P₂O₅/SiO₂ under solvent-free conditions and their depyranylation was written by Eshghi, Hossein;Rahimizadeh, Mohammad;Saberi, Sattar. And the article was included in Chinese Chemical Letters in 2008.SDS of cas: 60221-37-6 This article mentions the following:

Selective protection of one of the hydroxyl group in 1,n-sym. diols is achieved by P₂O₅/SiO₂-catalyzed reaction of the diol with dihydropyran under solvent-free conditions at room temperature This selective protection is simple and it occurred under economically cheap conditions in high yield. The deprotected diol is simply obtained by refluxing of this compound in methanol using the same catalyst without any byproduct formation or addnl. purifications. In the experiment, the researchers used many compounds, for example, 2-(2-(2-((Tetrahydro-2H-pyran-2-yl)oxy)ethoxy)ethoxy)ethan-1-ol (cas: 60221-37-6SDS of cas: 60221-37-6).

2-(2-(2-((Tetrahydro-2H-pyran-2-yl)oxy)ethoxy)ethoxy)ethan-1-ol (cas: 60221-37-6) belongs to ethers. The oxygen atom in ethers are more electronegative than carbon, thus the hydrogens which are alpha to the ethers are more acidic than the simple hydrocarbons. Ethers can form hydrogen bonds with other molecules (alcohols, amines, etc.) that have O―H or N―H bonds. The ability to form hydrogen bonds with other compounds makes ethers particularly good solvents for a wide variety of organic compounds and a surprisingly large number of inorganic compounds.SDS of cas: 60221-37-6

Referemce:
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Pyrolysis of fast growing wood Macaranga gigantea: Product characterisation and kinetic study was written by Subagyono, Rr dirgarini j. n.;Miten, Polonius Dosi;Sinaga, Ruth Junita;Wijayanti, Ardiana;Qi, Ying;Marshall, Marc;Sanjaya, Ari Susandy;Chaffee, Alan L.. And the article was included in Fuel in 2022.Safety of (4-Methoxyphenyl)methanol This article mentions the following:

Fast-growing wood Macaranga gigantea has been pyrolyzed and its pyrolysis products have been characterized and their formation kinetics studied. Pyrolysis of M. gigantea wood was carried out by varying the temperature and time of pyrolysis to determine the effect of these two parameters on product yields and product characteristics. In general, an increase in pyrolysis temperature and time increased the yield of liquid and gas products, the concentration of cellulose, hemicellulose and lignin-derived compounds, but decreased the biochar yield. The organic phase liquid pyrolysis products mainly contained phenolic compounds and their derivatives, eugenols, furans, aldehydes and ketones. Fourier-transform IR spectroscopy and pyrolysis-gas chromatog.-mass spectrometry analyses of biochar showed that thermal decomposition of M. gigantea required temperatures higher than 300°C to optimize thermal decomposition and carbonization of lignin, cellulose and hemicellulose. The concentration of phenols and benzenediols in biochar decreased with an increase in pyrolysis temperature M. gigantea pyrolysis kinetics studies showed that wood pyrolysis occurred through four main stages with activation energy (Eα) values, based on calculations by the Friedman and Kissinger-Akahira-Sunose methods, of 28.1-99.0 kJ/mol and 35.6-104.9 kJ/mol, resp. The spectra produced by thermogravimetric analyzer coupled with a Fourier-transform IR spectroscopy showed that H₂O and CO₂ were produced during pyrolysis and the volatile compounds produced were predominantly phenolic compounds, in accord with characterization results of the liquid products by gas chromatog.-mass spectrometry and NMR spectroscopy. In the experiment, the researchers used many compounds, for example, (4-Methoxyphenyl)methanol (cas: 105-13-5Safety of (4-Methoxyphenyl)methanol).

(4-Methoxyphenyl)methanol (cas: 105-13-5) belongs to ethers. Relative to alcohols, ethers are generally less dense, are less soluble in water, and have lower boiling points. They are relatively unreactive. Electron-deficient reagents are also stabilized by ethers. For example, borane (BH3) is a useful reagent for making alcohols. Pure borane exists as its dimer, diborane (B2H6), a toxic gas that is inconvenient and hazardous to use. Borane forms stable complexes with ethers, however, and it is often supplied and used as its liquid complex with tetrahydrofuran (THF).Safety of (4-Methoxyphenyl)methanol

Referemce:
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Enantioselective Dearomative [3 + 2] Umpolung Annulation of N-Heteroarenes with Alkynes was written by Yang, Peng;Wang, Qiang;Cui, Bing-Hui;Zhang, Xiao-Dong;Liu, Hang;Zhang, Yue-Yuan;Liu, Jia-Liang;Huang, Wen-Yu;Liang, Ren-Xiao;Jia, Yi-Xia. And the article was included in Journal of the American Chemical Society in 2022.Synthetic Route of C6H10O2 This article mentions the following:

Enantioselective [3 + 2] annulation of N-heteroarenes such as 2-(2-bromophenyl)quinoline with alkynes R¹CCR² [R¹ = Me, Ph, benzyloxymethyl, (thiophen-2-ylmethoxy)methyl, etc.; R² = Me, Ph, benzyloxymethyl, (thiophen-2-ylmethoxy)methyl, etc.] has been developed via a cobalt-catalyzed dearomative umpolung strategy in the presence of chiral ligand e.g., [(2R,3R)-3-(diphenylphosphanyl)butan-2-yl]diphenylphosphane and reducing reagent. A variety of electron-deficient N-heteroarenes e.g., 2-(2-bromophenyl)quinoline and internal or terminal alkynes are employed in this reaction, showing a broad substrate scope and good functionality tolerance. Annulation of electron-rich indoles I (R = H, 5-Cl) with alkynes is also developed. This protocol provides a straightforward access to a variety of N-spiroheterocyclic mols. such as II and in excellent enantioselectivities (76 examples, up to 99% ee). In the experiment, the researchers used many compounds, for example, 1,4-Dimethoxy-2-butyne (cas: 16356-02-8Synthetic Route of C6H10O2).

1,4-Dimethoxy-2-butyne (cas: 16356-02-8) belongs to ethers. Relative to alcohols, ethers are generally less dense, are less soluble in water, and have lower boiling points. They are relatively unreactive. Ethers can form hydrogen bonds with other molecules (alcohols, amines, etc.) that have O―H or N―H bonds. The ability to form hydrogen bonds with other compounds makes ethers particularly good solvents for a wide variety of organic compounds and a surprisingly large number of inorganic compounds.Synthetic Route of C6H10O2

Referemce:
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem