Month: February 2023

Modular Dual-Tasked C-H Methylation via the Catellani Strategy was written by Gao, Qianwen;Shang, Yong;Song, Fuzhen;Ye, Jinxiang;Liu, Ze-Shui;Li, Lisha;Cheng, Hong-Gang;Zhou, Qianghui. And the article was included in Journal of the American Chemical Society in 2019.Category: ethers-buliding-blocks This article mentions the following:

We report a dual-tasked methylation that is based on cooperative palladium/norbornene catalysis. Readily available (hetero)aryl halides (39 iodides and 4 bromides) and inexpensive MeOTs or trimethylphosphate are utilized as the substrates and methylating reagent, resp. Six types of “ipso” terminations can modularly couple with this “ortho” C-H methylation to constitute a versatile methylation toolbox for preparing diversified methylated arenes. This toolbox features inexpensive Me sources, excellent functional-group tolerance, simple reaction procedures, and scalability. Importantly, it can be uneventfully extended to isotope-labeled methylation by switching to the corresponding reagents CD₃OTs or ¹³CH₃OTs. Moreover, this toolbox can be applied to late-stage modification of biorelevant substrates with complete stereoretention. We believe these salient and practical features of our dual-tasked methylation toolbox will be welcomed by academic and industrial researchers. In the experiment, the researchers used many compounds, for example, 2-(3,5-Dimethoxyphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (cas: 365564-07-4Category: ethers-buliding-blocks).

2-(3,5-Dimethoxyphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (cas: 365564-07-4) 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. 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).Category: ethers-buliding-blocks

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

Nickel-Catalyzed Reductive Bis-Allylation of Alkynes was written by Komeyama, Kimihiro;Yamahata, Yuta;Osaka, Itaru. And the article was included in Organic Letters in 2018.Synthetic Route of C6H10O2 This article mentions the following:

A reductive nickel-catalyzed bis-allylation of alkynes with allyl acetates has been developed, leading to 1,4,7-triene skeletons. This reductive bis-allylation proceeds under mild conditions and exhibits good functional group tolerance in both the allyl acetates and the alkynes. 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. 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. 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.Synthetic Route of C6H10O2

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

Direct C-H Cyanoalkylation of Heteroaromatic N-Oxides and Quinones via C-C Bond Cleavage of Cyclobutanone Oximes was written by Gu, Yu-Rui;Duan, Xin-Hua;Yang, Lin;Guo, Li-Na. And the article was included in Organic Letters in 2017.Safety of 2,3-Dimethoxy-5-methylcyclohexa-2,5-diene-1,4-dione This article mentions the following:

A direct C-H cyanoalkylation of heteroaromatic N-oxides and quinones with cyclobutanone oximes is reported. This redox-neutral, operationally simple cyanoalkylation reaction is successfully amenable to a wide range of heteroaromatic N-oxides, quinones, and cyclobutanone oximes. A novel catalytic system consisting of a nickel source proved crucial for cleavage of the C-C bond of cyclobutanone oximes and for selective C-C bond formation over β-hydride elimination. Mechanistic studies suggest that a radical intermediate might be involved in this transformation. In the experiment, the researchers used many compounds, for example, 2,3-Dimethoxy-5-methylcyclohexa-2,5-diene-1,4-dione (cas: 605-94-7Safety of 2,3-Dimethoxy-5-methylcyclohexa-2,5-diene-1,4-dione).

2,3-Dimethoxy-5-methylcyclohexa-2,5-diene-1,4-dione (cas: 605-94-7) 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. Autoxidation is the spontaneous oxidation of a compound in air. In the presence of oxygen, ethers slowly autoxidize to form hydroperoxides and dialkyl peroxides. If concentrated or heated, these peroxides may explode. To prevent such explosions, ethers should be obtained in small quantities, kept in tightly sealed containers, and used promptly.Safety of 2,3-Dimethoxy-5-methylcyclohexa-2,5-diene-1,4-dione

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

Rapid heteroatom transfer to arylmetals utilizing multifunctional reagent scaffolds was written by Gao, Hongyin;Zhou, Zhe;Kwon, Doo-Hyun;Coombs, James;Jones, Steven;Behnke, Nicole Erin;Ess, Daniel H.;Kurti, Laszlo. And the article was included in Nature Chemistry in 2017.Related Products of 104197-14-0 This article mentions the following:

Arylmetal reagents generated in situ from aryl bromides, aryl iodides, or arenes underwent chemoselective amination or hydroxylation reactions with an N-H oxaziridine and an N-benzyl oxaziridine derived from (-)-fenchone and racemic camphor, resp., to yield primary arylamines (as their free bases) and phenols, resp. The method does not use transition metal catalysts or added ligands or catalysts and does not require excess amounts of oxaziridine or nitrogen protecting groups. The structures of transition states leading to amination, hydroxylation, and proton transfer reactions were determined by DFT calculations to understand the chemoselectivity of N-H and N-protected aziridine reactions with 2-naphthylmagnesium bromide. In the experiment, the researchers used many compounds, for example, 4-Bromo-2,6-difluoroanisole (cas: 104197-14-0Related Products of 104197-14-0).

4-Bromo-2,6-difluoroanisole (cas: 104197-14-0) 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. 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.Related Products of 104197-14-0

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

Ionic transport and mechanical properties of slide-ring gel swollen with Mg-ion electrolytes was written by Nishino, Haruka;Liu, Chang;Kanehashi, Shinji;Mayumi, Koichi;Tominaga, Yoichi;Shimomura, Takeshi;Ito, Kohzo. And the article was included in Ionics in 2020.Reference of 112-49-2 This article mentions the following:

The authors applied a slide-ring (SR) gel to a Mg²⁺ ion gel electrolyte and clarified the elec. and mech. properties in order to achieve a Mg²⁺ ion gel electrolyte with both sufficient mech. strength and high ionic conductivity The SR gel is made from polyrotaxane, which has a structure that consists of cyclic mols., α-cyclodextrins (CDs), threaded by an axial polymer chain, polyethylene glycol (PEG), and crosslinked by divinyl sulfone. Pure glymes and tetraethylene glycol di-Me ether (tetraglyme: G4) dissolving Mg²⁺ ions had no ability to swell the SR gel, whereas diethylene glycol di-Me ether (diglyme: G2) and triethylene glycol di-Me ether (triglyme: G3) dissolving Mg²⁺ ions were able to swell the SR gel. The swelling behavior was strongly dependent on the interaction between Mg²⁺ ions complexed with glymes and ether oxygens of a PEG-based hydroxypropyl PR (HyPR) network. Upon tensile elongation, SR gel swollen with G3 solution dissolving Mg²⁺ ions could be extended by 300%, which indicated the unique property of high ductility. The ionic conductivity of SR gel swollen with G3 dissolving Mg²⁺ ions, which approx. satisfied a Vogel-Tamman-Fulcher (VTF) dependence, was 1.73 mS cm^-1 at room temperature, and the molar conductivity was 67% of that for a pristine G3 solution dissolving Mg²⁺ ions. In the experiment, the researchers used many compounds, for example, 2,5,8,11-Tetraoxadodecane (cas: 112-49-2Reference of 112-49-2).

2,5,8,11-Tetraoxadodecane (cas: 112-49-2) 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. 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.Reference of 112-49-2

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

Antibacterial Activity and Mechanism of Coenzyme Q₀ Against Escherichia coli was written by Wang, Ruixia;Li, Jiahui;Qu, Geruo;Guo, Du;Yang, Yanpeng;Ma, Xiaoyu;Wang, Muxue;Xu, Yunfeng;Wang, Yutang;Xia, Xiaodong;Shi, Chao. And the article was included in Foodborne Pathogens and Disease in 2021.Application of 605-94-7 This article mentions the following:

Coenzyme Q₀ (CoQ₀) is a natural compound found in Antrodia cinnamomea, which has a variety of biol. activities. Here, the antibacterial activity and possible antibacterial mechanism of CoQ₀ against Escherichia coli were investigated. The antibacterial effect was evaluated by determining min. inhibitory concentration (MIC) and min. bactericidal concentration (MBC) values, and by assessing bacterial survival and the effect on the growth of E. coli after CoQ₀ treatment in Luria-Bertani (LB) broth. To reveal the antibacterial mechanism of CoQ₀, changes in intracellular ATP (ATP) concentration, membrane potential, and bacterial protein content, as well as effects on cell morphol. and membrane integrity, were investigated. Both the MICs and MBCs of CoQ₀ against E. coli were 0.1 mg/mL. After treatment of E. coli (6.5 log colony-forming units/mL) with 0.1 mg/mL of CoQ₀ in LB broth for 3 h, the number of viable cells dropped below the detection limit. In addition, CoQ₀ treatment resulted in the reduction in intracellular ATP concentration, cell membrane hyperpolarization, decreased bacterial protein concentrations, and damage to cell membrane integrity and cellular morphol. These results indicated that CoQ₀ has effective antibacterial activity against E. coli, suggesting potential applications in food industry safety. In the experiment, the researchers used many compounds, for example, 2,3-Dimethoxy-5-methylcyclohexa-2,5-diene-1,4-dione (cas: 605-94-7Application of 605-94-7).

2,3-Dimethoxy-5-methylcyclohexa-2,5-diene-1,4-dione (cas: 605-94-7) 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. 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.Application of 605-94-7

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

syn-Diastereoselective glycolate aldol addition reactions of an N(3)-(p-methoxyphenoxy)acetyloxazolidine-2-thione was written by Haynes, Craig S.;Goodman, Cassie A.;Bruce, Juandah;Genin, Sarah C.;Austermuehle, Brad J.;Leong, Victor L.;Leise, Austin R.;Larson, Robert;Hamaker, Christopher G.;Hitchcock, Shawn R.. And the article was included in Tetrahedron: Asymmetry in 2017.Application of 1877-75-4 This article mentions the following:

An N₃-(p-methoxyphenoxy)acetyloxazolidine-2-thione was synthesized and employed in glycolate asym. aldol addition reactions with aromatic and aliphatic aldehydes. It was determined that the titanium tetrachloride medicated aldol reaction afforded diastereoselectivities that ranged from 75:25 to 94:6 when the reaction was conducted at -78°. The absolute stereochem. of the aldol adducts was determined by ¹H NMR spectroscopy and X-ray crystallog. The ¹H NMR spectra of the aldol adducts contained a signal (the α-proton of the glycolate position of the aldol side chain) that was highly deshielded due to conformational restriction about the N(3)-(p-methoxyphenoxy)acetyl side chain and the oxazolidine-2-thione auxiliary. In the experiment, the researchers used many compounds, for example, 2-(4-Methoxyphenoxy)acetic acid (cas: 1877-75-4Application of 1877-75-4).

2-(4-Methoxyphenoxy)acetic acid (cas: 1877-75-4) 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. But on the other hand, ethers undergo cleavage by reaction with acids. 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.Application of 1877-75-4

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

Concise access to perimidines by palladium (II) complexes via acceptorless dehydrogenative coupling of alcohols was written by Clinton, Savarimuthu Selvan;Ramesh, Rengan;Malecki, Jan Grzegorz. And the article was included in Applied Organometallic Chemistry in 2022.Related Products of 105-13-5 This article mentions the following:

A facile protocol for the one-pot synthesis of 2,3-dihydro-1H-perimidines via dehydrogenative coupling of easily exploitable benzyl alcs. supported by new Pd(II) complexes has been reported. To accomplish the construction of perimidines, a new set of palladium(II) complexes [Pd(L)Cl (PPh₃)] encompassing biphenyl benzhydrazone ligands I has been reported as catalysts. Structural characterization by elemental anal., FT-IR, NMR (¹H and ¹³C), and mass spectral analyses confirmed the composition of synthesized complexes. The mol. structures of complexes I(R = H, OCH₃), were unequivocally resolved using single-crystal X-ray diffraction. It reveals that the complex espoused distorted square-planar geometry around Pd(II) ion chelated by azomethine nitrogen and imidolate oxygen of biphenyl benzhydrazone ligands with labile chloride and a triphenylphosphine. Further, the selective synthesis of a broad range of functionalized perimidines has been accomplished via ADC of a variety of alcs. with 1,8-diaminonaphthalene. The palladium complexes mediated catalytic synthesis offered good yields of perimidines up to 86% using only 0.5 mol% catalyst loading. A probable mechanism to the formation of perimidines was postulated from the results of control exptl. investigations. The environmentally compassionate, greener ADC protocol progresses via the generation of aldehyde intermediate and releases only water and hydrogen gas. In the experiment, the researchers used many compounds, for example, (4-Methoxyphenyl)methanol (cas: 105-13-5Related Products of 105-13-5).

(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).Related Products of 105-13-5

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

Host-guest complexation. 9. Macrocyclic polyethers and sulfides shaped by one rigid dinaphthyl unit and attached arms. Synthesis and survey of complexing abilities was written by Cram, Donald J.;Helgeson, Roger C.;Koga, Kenji;Kyba, Evan P.;Madan, Khorshed;Sousa, Lynn R.;Siegel, Merrell G.;Moreau, Patrice;Gokel, George W.. And the article was included in Journal of Organic Chemistry in 1978.Electric Literature of C11H16O3 This article mentions the following:

The synthesis and characterization of a stereoisomeric macrocyclic polyether, e.g., I (R, R² = H, CH₂OH, CH₂OCH₂CO₂Me, etc.; R¹ = H, Br, COMe, etc.) and polyether-polythioether hosts are described. The unshared electron pairs of the heteroatoms act as binding sites for metal or alkylammonium cations. Substituents attached at the 3,3′-positions of the 1,1′-binaphthyl unit converge on and provide addnl. shape to the space surrounding the central binding hole of the macro ring. Certain of these units terminate in functional groups that provide addnl. ligands for cationic guests, in some cases supplying counterions for the charge on the guests. Substituents attached at the 6,6′-positions of the 1,1′-binaphthyl unit diverge from the macro ring and its environment and can be used to manipulate solubility properties or to bind the hosts to solid supports. Substituents attached at the 3- or 4-positions of the 1,2-benzene units, when long enough and in the proper conformations, can curl to place addnl. binding sites on the edge of the macro ring. The maximum rotations and absolute configurations of some of the optically active hosts were determined Ring closures (6-65% yield) involved aryloxide- or arylsulfide-anion substitutions on appropriate alkyl ditosylates. In the experiment, the researchers used many compounds, for example, 3-(3,4-Dimethoxyphenyl)propan-1-ol (cas: 3929-47-3Electric Literature of C11H16O3).

3-(3,4-Dimethoxyphenyl)propan-1-ol (cas: 3929-47-3) 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. 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).Electric Literature of C11H16O3

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

Photochromic polyphosphazenes with spiropyran units was written by Allcock, Harry R.;Kim, Chulhee. And the article was included in Macromolecules in 1991.Name: 2-(2-(2-((Tetrahydro-2H-pyran-2-yl)oxy)ethoxy)ethoxy)ethan-1-ol This article mentions the following:

Photochromic spiropyrans were linked to polyphosphazenes through O(CH₂CH₂O)_nO (n = 2, 3) spacers. The reversion of photogenerated merocyanine groups to spiropyran units in the solid state was much slower than in solution (increasing with increasing polarity for the latter). Solid-state reversion was slower for a polymer containing all spiropyran units than for one containing mixed substituents, presumably a steric effect. Reversion was slower for polymers with a diethyleneoxy spacer than with a triethyleneoxy unit. Reversions in THF and the solid state were modeled by a biexponential process. The overall phenomena were explained by the solvation or aggregation of the polymer chains in solution as well as by the existence of 2 different environments for the merocyanine units. 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: 60221-37-6Name: 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. 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 feature bent C–O–C linkages. In dimethyl ether, the bond angle is 111° and C–O distances are 141 pm. The barrier to rotation about the C–O bonds is low. The bonding of oxygen in ethers, alcohols, and water is similar. In the language of valence bond theory, the hybridization at oxygen is sp3.Name: 2-(2-(2-((Tetrahydro-2H-pyran-2-yl)oxy)ethoxy)ethoxy)ethan-1-ol

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