Category: ethers-buliding-blocks

Copper-catalyzed ortho-alkenylation of quinoline N-oxides with alkynes was written by Jiang, Linjuan;Hu, Hui;Liu, Yuanhong. And the article was included in Organic Chemistry Frontiers in 2022.Related Products of 16356-02-8 This article mentions the following:

A copper-catalyzed regioselective C-2 alkenylation of quinoline N-oxides with alkynes and pinacol diborane was developed. This method provided efficient access to a wide variety of deoxygenated 2-alkenyl quinolines with good functional group tolerance. In particular, highly regio- and stereoselective reactions were observed with unsym. alkynes such as aryl(alkyl)acetylenes and enynes. The reaction involved borylcupration of alkynes, captured of the catalytically generated alkenyl copper species by quinoline N-oxides and deborylation. In the experiment, the researchers used many compounds, for example, 1,4-Dimethoxy-2-butyne (cas: 16356-02-8Related Products of 16356-02-8).

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, 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. 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 16356-02-8

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

Synthesis of 2-[(aryloxy)methyl]benzimidazole derivatives was written by Cui, Wen-hui;Zhang, You-min;Wei, Tai-bao. And the article was included in Hecheng Huaxue in 2006.Electric Literature of C9H10O4 This article mentions the following:

Twelve derivatives of 2-[(aryloxy)methyl]-1H-benzimidazole were synthesized using HCl as a catalyst and the structures were identified by ¹H NMR, IR and elemental anal. Six of the compounds are reported for the first time. In the experiment, the researchers used many compounds, for example, 2-(4-Methoxyphenoxy)acetic acid (cas: 1877-75-4Electric Literature of C9H10O4).

2-(4-Methoxyphenoxy)acetic acid (cas: 1877-75-4) 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.Electric Literature of C9H10O4

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

Aromatic Homologation by Non-Chelate-Assisted Rh^III-Catalyzed C-H Functionalization of Arenes with Alkynes was written by Pham, Manh V.;Cramer, Nicolai. And the article was included in Angewandte Chemie, International Edition in 2014.Electric Literature of C6H10O2 This article mentions the following:

Larger condensed arenes are of interest owing to their electro- and photochem. properties. An efficient synthesis is the catalyzed aromatic annulation of a smaller arene with two alkyne mols. Besides difunctionalized starting materials, directed C-H functionalization can be used for such aromatic homologation. However, thus far the requirement of either pre-functionalized substrates or suitable directing groups were limiting this approach. Herein, we describe a rhodium(III)-catalyzed method allowing the use of completely unbiased arenes and internal alkynes. The reaction works best with copper(II) 2-ethylhexanoate and decabromodiphenyl ether as the oxidant combination. E.g., in presence of [(Cp^*RhCl₂)₂], copper(II) 2-ethylhexanoate, and decabromodiphenyl ether, homologation of naphthalene with BuCCBu gave 60% anthracene derivative (I). This aromatic annulation tolerates a variety of functional groups and delivers homologated condensed arenes. Aside from simple benzenes, naphthalenes, and higher condensed arenes provide access to highly substituted and highly soluble acene structures having important electronic and photophys. properties. In the experiment, the researchers used many compounds, for example, 1,4-Dimethoxy-2-butyne (cas: 16356-02-8Electric Literature of C6H10O2).

1,4-Dimethoxy-2-butyne (cas: 16356-02-8) 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. 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.Electric Literature of C6H10O2

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

Total Synthesis of a Noricumazole A Library and Evaluation of HCV Inhibition was written by Barbier, Jenny;Wegner, Jens;Benson, Stefan;Gentzsch, Juliane;Pietschmann, Thomas;Kirschning, Andreas. And the article was included in Chemistry – A European Journal in 2012.Computed Properties of C8H9BO4 This article mentions the following:

The total synthesis of 16 new ion channel inhibitors derived from noricumazole A I (X = O), a secondary metabolite from the myxobacterium Sorangium cellulosum, is reported. Particular focus of library design is put on stereochem. permutations in the central region (C9 and C11), the oxazole moiety and the side chain at C4 of the isochromanone moiety. Noricumazole A and all new noricumazole derivatives were tested in an assay system to determine the inhibitory effect on the hepatitis C virus (HCV) life cycle. Most of the compounds are moderate to strong HCV inhibitors (350 nM-6 nM), but also exert pronounced cytotoxicity. In contrast, the thiazole analog of noricumazole A, I (X = S), is a strong HCV inhibitor with only moderate cytotoxic property. It may become a lead structure with a good therapeutic index (CC₅₀/IC₅₀) of greater than 10. In the experiment, the researchers used many compounds, for example, 3-Formyl-2-methoxyphenylboronic acid (cas: 480424-49-5Computed Properties of C8H9BO4).

3-Formyl-2-methoxyphenylboronic acid (cas: 480424-49-5) 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. 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.Computed Properties of C8H9BO4

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

Microwave-assisted synthesis of 4-amino-3-[2-benzo[b]furyl]-5-mercapto-1,2,4-triazole and its derivatives was written by Wang, Xi-Cun;Quan, Zheng-Jun;Li, Zheng. And the article was included in Youji Huaxue in 2005.Electric Literature of C9H10O4 This article mentions the following:

4-Amino-3-(2-benzofuryl)-5-mercapto-1,2,4-triazole was synthesized by the reactions of 2-benzo[b]furoyl hydrazine with CS₂ and next hydrazine under microwave irradiation Treatment of the resulting 4-amino-5-mercapto-1,2,4-triazole with aromatic carboxylic acids (or aryloxyacetic acids), α-bromoacetophenones and aromatic aldehydes under microwave irradiation yielded the corresponding 1,2,4-triazolo[3,4-b]-1,3,4-thiadiazoles, 1,2,4-triazolo[3,4-b]-1,3,4-thiadiazines and 4-arylideneamino-5-mercapto-1,2,4-triazole in good to moderate yields, resp. The structures of all these new compounds were confirmed by elemental analyses, IR, ¹H NMR and MS spectra. In the experiment, the researchers used many compounds, for example, 2-(4-Methoxyphenoxy)acetic acid (cas: 1877-75-4Electric Literature of C9H10O4).

2-(4-Methoxyphenoxy)acetic acid (cas: 1877-75-4) 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.Electric Literature of C9H10O4

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

Hypervalent Iodine(III)-Induced Intramolecular Cyclization of α-(Aryl)alkyl-β-dicarbonyl Compounds: A Convenient Synthesis of Benzannulated and Spirobenzannulated Compounds was written by Arisawa, Mitsuhiro;Ramesh, Namakkal G.;Nakajima, Makiko;Tohma, Hirofumi;Kita, Yasuyuki. And the article was included in Journal of Organic Chemistry in 2001.Application of 3929-47-3 This article mentions the following:

A novel hypervalent iodine(III)-induced direct intramol. cyclization of α-(aryl)alkyl-β-dicarbonyl compounds has been described. Both meta- and para-substituted phenol ether derivatives containing acyclic or cyclic 1,3-dicarbonyl moieties at the side chain undergo this reaction in a facile manner. The reactions afford benzannulated and spirobenzannulated compounds that are of biol. importance. The reaction is found to be general, mild, and high yielding. The mechanism of the reaction has been shown to involve a cation radical intermediate. In the experiment, the researchers used many compounds, for example, 3-(3,4-Dimethoxyphenyl)propan-1-ol (cas: 3929-47-3Application of 3929-47-3).

3-(3,4-Dimethoxyphenyl)propan-1-ol (cas: 3929-47-3) 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. 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 3929-47-3

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

Synthetic studies on indoles and related compounds. 49. Unexpected formation of quinolone derivatives in Reissert indole synthesis was written by Suzuki, Hideharu;Gyoutoku, Hiroshi;Yokoo, Hiroe;Shinba, Mika;Sato, Yuka;Yamada, Hiroshi;Murakami, Yasuoki. And the article was included in Synlett in 2000.Quality Control of 3-Methyl-4-nitroanisole This article mentions the following:

The Reissert indole synthesis was found to unexpectedly give 3-hydroxy-1,2,3,4-tetrahydro-2-quinolone derivatives I (R = H, 6-MeO, 5-MeO, 3-CO₂Et, 3-Me, 3-MeO, 3-Me₂CHO), sometimes in a high ratio to the expected Et indole-2-carboxylate derivatives, depending on the conditions of the catalytic reduction of the intermediate (2-nitrophenyl)pyruvates. This reactivity is characteristic in the preparation of 7-substituted indoles. In the experiment, the researchers used many compounds, for example, 3-Methyl-4-nitroanisole (cas: 5367-32-8Quality Control of 3-Methyl-4-nitroanisole).

3-Methyl-4-nitroanisole (cas: 5367-32-8) 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. 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.Quality Control of 3-Methyl-4-nitroanisole

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

Phosphorylated cyclopropanes in the synthesis of α-alkylidene-γ-butyrolactones: total synthesis of (±)-savinin, (±)-gadain and (±)-peperomin E was written by Lloyd, Matthew G.;Taylor, Richard J. K.;Unsworth, William P.. And the article was included in Organic & Biomolecular Chemistry in 2016.Formula: C11H16O3 This article mentions the following:

Phosphorylated cyclopropanes, generated via the Rh(II)-catalyzed intramol. cyclopropanation of α-(diethoxyphosphoryl)acetates, have been found to be useful precursors in the synthesis of α-alkylidene-γ-butyrolactones. These cyclopropyl intermediates undergo regioselective reductive ring-opening and subsequent Horner-Wadsworth-Emmons olefination to complete the synthesis. Total syntheses of (±)-savinin (I) and (±)-gadain (II), as well as the first total synthesis of (±)-peperomin E (III), are all described using this method. In the experiment, the researchers used many compounds, for example, 3-(3,4-Dimethoxyphenyl)propan-1-ol (cas: 3929-47-3Formula: C11H16O3).

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

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

Disilanes as oxygen scavengers and surrogates of hydrosilanes suitable for selective reduction of nitroarenes, phosphine oxides and other valuable substrates was written by Gevorgyan, Ashot;Mkrtchyan, Satenik;Grigoryan, Tatevik;Iaroshenko, Viktor O.. And the article was included in Organic Chemistry Frontiers in 2017.Computed Properties of C8H9NO3 This article mentions the following:

In this report, the reaction of nitroarenes RNO₂ (R = Pr, cyclohexyl, 2-methylphenyl, pyridin-3-yl, etc.) with hexamethyldisilane under various conditions affords a different range of compounds with excellent selectivity. In particular, the reaction of nitroarenes with hexamethyldisilane using a CsF/TBAB/toluene system provides suitable azo compounds, while in the presence of a CsF/TBAB/[Pd]/EtOH system this hexamethyldisilane acts as a novel surrogate of gaseous trimethylsilane, thus, reducing nitroarenes to corresponding anilines RNH₂. The synthetic value of the developed methodol. was further extended by the reduction of a wide range of substrates including N-oxides such as 2-methyl-quinoline-1-oxide, isoquinoline-2-oxide, 2,6-dimethylpyridine-1-oxide, 2-phenylpyridine-1-oxide, sulfoxides such as methanesulfinylbenzene, (benzenesulfinyl)benzene, 1-methanesulfinyl-4-methylbenzene, [(phenylmethane)sulfinylmethyl]benzene, phosphine oxides such as [[(diphenylphosphoroso)methyl](phenyl)phosphoryl]benzene, [[3-(diphenylphosphoroso)propyl](phenyl)phosphoryl]benzene, (diphenylphosphoryl)benzene, etc. In the experiment, the researchers used many compounds, for example, 3-Methyl-4-nitroanisole (cas: 5367-32-8Computed Properties of C8H9NO3).

3-Methyl-4-nitroanisole (cas: 5367-32-8) 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. 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.Computed Properties of C8H9NO3

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

Structural basis for gating mechanisms of a eukaryotic P-glycoprotein homolog was written by Kodan, Atsushi;Yamaguchi, Tomohiro;Nakatsu, Toru;Sakiyama, Keita;Hipolito, Christopher J.;Fujioka, Akane;Hirokane, Ryo;Ikeguchi, Keiji;Watanabe, Bunta;Hiratake, Jun;Kimura, Yasuhisa;Suga, Hiroaki;Ueda, Kazumitsu;Kato, Hiroaki. And the article was included in Proceedings of the National Academy of Sciences of the United States of America in 2014.Related Products of 3929-47-3 This article mentions the following:

P-glycoprotein is an ATP-binding cassette multidrug transporter that actively transports chem. diverse substrates across the lipid bilayer. The precise mol. mechanism underlying transport is not fully understood. Here, the authors present crystal structures of a eukaryotic P-glycoprotein homolog, CmABCB1 with ATPase activity from Cyanidioschyzon merolae, in 2 forms: unbound at 2.6-Å resolution and bound to a unique allosteric peptide inhibitor at 2.4-Å resolution The inhibitor clamped the transmembrane helixes from the outside, fixing the CmABCB1 structure in an inward-open conformation similar to the unbound structure, confirming that an outward-opening motion is required for the ATP hydrolysis cycle. These structures, along with site-directed mutagenesis and transporter activity measurements, revealed the detailed architecture of the transporter, including a gate that opens to extracellular side and 2 gates that open to intramembranous region and the cytosolic side. The authors propose that the motion of the nucleotide-binding domain drives those gating apparatuses via 2 short intracellular helixes, IH1 and IH2, and 2 transmembrane helixes, TM2 and TM5. In the experiment, the researchers used many compounds, for example, 3-(3,4-Dimethoxyphenyl)propan-1-ol (cas: 3929-47-3Related Products of 3929-47-3).

3-(3,4-Dimethoxyphenyl)propan-1-ol (cas: 3929-47-3) 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. 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 3929-47-3

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