Category: ethers-buliding-blocks

Mono-N-Alkylation of Sulfonamides with Alcohols Catalyzed by Iridium N-Heterocyclic Carbene-Phosphine Complexes was written by Li, Xingzhen;Peters, Bram B. C.;Tan, Min;He, Lei;Yang, Jianping;Andersson, Pher G.;Zhou, Taigang. And the article was included in Asian Journal of Organic Chemistry in 2022.Application of 105-13-5 This article mentions the following:

A N-heterocyclic carbene-phosphine iridium complex was presented for the efficient and selective mono-N-alkylation of sulfonamides with alcs. based on a borrowing hydrogenation strategy. Herein, water was the only byproduct and this methodol. thus offered a more environmentally benign and interesting alternative to the use of traditional alkylating reagents. This facile protocol tolerated a large number of (hetero) aromatic and aliphatic sulfonamides as well as (hetero) aromatic and aliphatic alcs. to obtain the desired product is high isolated yield (up to 98%). The alkylation completely retarded after the formation of the secondary sulfonamide and no over-alkylation was observed in all cases. The option to run the reaction under solvent-free conditions as well as the scalability of this borrowing hydrogenation were key features of this protocol. In the experiment, the researchers used many compounds, for example, (4-Methoxyphenyl)methanol (cas: 105-13-5Application of 105-13-5).

(4-Methoxyphenyl)methanol (cas: 105-13-5) 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. 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.Application of 105-13-5

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

Insights into the polymerization kinetics of thermoresponsive polytrimethylene carbonate bearing a methoxyethoxy side group was written by Brissenden, Amanda J.;Amsden, Brian G.. And the article was included in Journal of Polymer Science (Hoboken, NJ, United States) in 2020.Product Details of 111-77-3 This article mentions the following:

The ring-opening polymerization kinetics of 5-[2-(2-methoxyethoxy)-ethoxymethyl]-5-methyl-1,3-dioxa-2-one (TMOE-2) and 5-[2-{2-(2-methoxyethoxy)ethyoxy}-ethoxymethyl]-5-methyl-1,3-dioxa-2-one (TMOE-3) was investigated using different catalysts with the aim to improve control over mol. weight The possibility of monomer impurities driving the variability in mol. weight that has been seen in different reports, was assessed and evidence of catalysis via an imidazole impurity was found. The catalysts 1,5,7-triazobicyclo(4.4.0)dec-5-ene (TBD), hydrogen chloride in di-Et ether (HCl.Et₂O), stannous 2-ethylhexanoate (SnOct₂), and catalyst free thermal polymerizations were conducted to understand the mechanisms influencing the mol. weight TBD and HCl.Et₂O consistently achieved high conversion of the monomer; however, mol. weights greater than 7,000 Da could not be achieved due to competing side reactions. SnOct₂ catalyzed and catalyst free thermal polymerizations were highly influenced by monomer purity and achieved lower conversion than TBD and HCl.Et₂O. Understanding these mechanisms will guide future synthesis of poly(TMOE-2) and poly(TMOE-3) for biomedical applications. In the experiment, the researchers used many compounds, for example, 2-(2-Methoxyethoxy)ethanol (cas: 111-77-3Product Details of 111-77-3).

2-(2-Methoxyethoxy)ethanol (cas: 111-77-3) 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. 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.Product Details of 111-77-3

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

Chemical Constituents from the Fungus Antrodia cinnamomea was written by Wu, Ming-Der;Cheng, Ming-Jen;Chen, Yen-Lin;Hsun-Hsuo-Chang;Kuo, Yueh-Hsiung;Lin, Chih-Chuan;Wu, Ho-Cheng. And the article was included in Natural Product Communications in 2019.Related Products of 605-94-7 This article mentions the following:

A new benzenoid, 4-methoxy-7-methylbenzo[d][1,3]dioxol-5-ol (1) and three known secondary metabolites 2,3-dimethoxy-5-methyl[1,4]benzoquinone (2), 2-methoxy-6-methyl-1,4-benzoquinone (3) and 5-methyl-benzo[1,3]dioxole-4,7-diol (4) were isolated from the mycelia of A. cinnamomea BCRC 36799 by solid state fermentation with adlay. Their chem. structures were elucidated on the basis of HRESIMS, NMR spectroscopic data and comparison with reported values. All isolated compounds 1-4 were tested for their cytotoxicity against the six cancer cell lines using the MTT assay. Among them, compound 3 displayed significant cytotoxic effects toward all six tested cancer cell lines, with IC₅₀ values ranging from 2.8-8.7 μM in vitro. In the experiment, the researchers used many compounds, for example, 2,3-Dimethoxy-5-methylcyclohexa-2,5-diene-1,4-dione (cas: 605-94-7Related Products of 605-94-7).

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

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

Comprehensive transcriptomic and proteomic analyses of antroquinonol biosynthetic genes and enzymes in Antrodia camphorata was written by Liu, Xiaofeng;Xia, Yongjun;Zhang, Yao;Yang, Caiyun;Xiong, Zhiqiang;Song, Xin;Ai, Lianzhong. And the article was included in AMB Express in 2020.COA of Formula: C9H10O4 This article mentions the following:

Abstract: Antroquinonol (AQ) has several remarkable bioactivities in acute myeloid leukemia and pancreatic cancer, but difficulties in the mass production of AQ hamper its applications. Currently, mol. biotechnol. methods, such as gene overexpression, have been widely used to increase the production of metabolites. However, AQ biosynthetic genes and enzymes are poorly understood. In this study, an integrated study coupling RNA-Seq and isobaric tags for relative and absolute quantitation (iTRAQ) were used to identify AQ synthesis-related genes and enzymes in Antrodia camphorata during coenzyme Q₀-induced fermentation (FM). The upregulated genes related to acetyl-CoA synthesis indicated that acetyl-CoA enters the mevalonate pathway to form the farnesyl tail precursor of AQ. The metE gene for an enzyme with Me transfer activity provided sufficient Me groups for AQ structure formation. The CoQ2 and ubiA genes encode p-hydroxybenzoate polyprenyl transferase, linking coenzyme Q₀ and the polyisoprene side chain to form coenzyme Q₃. NADH is transformed into NAD+ and releases two electrons, which may be beneficial for the conversion of coenzyme Q₃ to AQ. Understanding the biosynthetic genes and enzymes of AQ is important for improving its production by genetic means in the future. In the experiment, the researchers used many compounds, for example, 2,3-Dimethoxy-5-methylcyclohexa-2,5-diene-1,4-dione (cas: 605-94-7COA of Formula: C9H10O4).

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. The unique properties of ethers (i.e., that they are strongly polar, with nonbonding electron pairs but no hydroxyl group) enhance the formation and use of many reagents. For example, Grignard reagents cannot form unless an ether is present to share its lone pair of electrons with the magnesium atom. Complexation of the magnesium atom stabilizes the Grignard reagent and helps to keep it in solution.COA of Formula: C9H10O4

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

New highly soluble triarylamine-based materials as promising catholytes for redox flow batteries was written by Romadina, Elena I.;Volodin, Ivan A.;Stevenson, Keith J.;Troshin, Pavel A.. And the article was included in Journal of Materials Chemistry A: Materials for Energy and Sustainability in 2021.Computed Properties of C5H12O3 This article mentions the following:

A series of arylamines bearing oligoethylene glycol ether solubilizing moieties were designed and comprehensively evaluated as promising catholyte materials for non-aqueous redox flow batteries (RFBs). The triphenylamine core maintains the chem. stability of the radical cation, the ethylene glycol chains enhance the solubility up to complete miscibility with organic solvents, and the electron-withdrawing bromine substituents increase the redox potential of the compounds up to 0.61 V vs. Ag/AgNO₃. The best material showed 99% coulombic efficiency in combination with good stability in over 50 charge-discharge cycles in laboratory RFB cells. The designed triarylamine-based catholyte materials appear promising for the development of next-generation high-voltage and high-capacity RFBs. In the experiment, the researchers used many compounds, for example, 2-(2-Methoxyethoxy)ethanol (cas: 111-77-3Computed Properties of C5H12O3).

2-(2-Methoxyethoxy)ethanol (cas: 111-77-3) 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).Computed Properties of C5H12O3

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

Temperature dependence of industrial propylene glycol alkyl ether/water mixtures was written by Bauduin, P.;Wattebled, L.;Schrodle, S.;Touraud, D.;Kunz, W.. And the article was included in Journal of Molecular Liquids in 2004.Application of 20324-33-8 This article mentions the following:

The miscibility of ten industrially used propylene glycol ethers with water is studied in the temperature range between 0 and 80 °C. Several of these systems show a lower critical point of demixing near room temperature The shapes of the phase diagrams are discussed in detail and compared to those of the widely used but potentially toxic ethylene glycol alkyl ether/water mixtures In the experiment, the researchers used many compounds, for example, 1-((1-((1-Methoxypropan-2-yl)oxy)propan-2-yl)oxy)propan-2-ol (cas: 20324-33-8Application of 20324-33-8).

1-((1-((1-Methoxypropan-2-yl)oxy)propan-2-yl)oxy)propan-2-ol (cas: 20324-33-8) 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).Application of 20324-33-8

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

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

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

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