Category: ethers-buliding-blocks

Iridium Catalyzed Carbocyclizations: Efficient (5+2) Cycloadditions of Vinylcyclopropanes and Alkynes was written by Melcher, Michaela-Christina;von Wachenfeldt, Henrik;Sundin, Anders;Strand, Daniel. And the article was included in Chemistry – A European Journal in 2015.Recommanded Product: 1,4-Dimethoxy-2-butyne This article mentions the following:

Third-row transition metal catalysts remain a largely untapped resource in cycloaddition reactions for the formation of medium-sized rings. Herein, we report the first examples of iridium-catalyzed inter- and intramol. vinylcyclopropane (VCP)-alkyne (5+2) cycloadditions DFT modeling suggests that catalysis by iridium(I) proceeds through a mechanism similar to that previously reported for rhodium(I)-catalyzed VCP-alkyne cycloadditions, but a smaller free energy span for iridium enables substantially faster catalysis under favorable conditions. The system is characterized by up to quant. yields and is amenable to an array of disubstituted alkynes and vinylcyclopropanes. In the experiment, the researchers used many compounds, for example, 1,4-Dimethoxy-2-butyne (cas: 16356-02-8Recommanded Product: 1,4-Dimethoxy-2-butyne).

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.Recommanded Product: 1,4-Dimethoxy-2-butyne

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

More insight into the chemical composition of Greek propolis; differences and similarities with Turkish propolis was written by Celemli, Omur G.;Hatjina, Fani;Charistos, Leonidas;Schiesser, Aygun;Ozkirim, Asli. And the article was included in Zeitschrift fuer Naturforschung, C: Journal of Biosciences in 2013.Recommanded Product: 6972-61-8 This article mentions the following:

We aimed to determine the differences and similarities between Greek and Turkish propolis with respect to their chem. composition given that the two countries have many similarities in oral biodiversity. We observed that: a) Greek propolis is different from the European-type propolis, having a high terpene content; therefore we can deinitely characterize it as a Mediterranean type; b) the Turkish propolis collected along the coast line of the Aegean Sea is similiar to the examined Greek propolis; c) the remaining Turkish samples, originating from the European part of Turkey, were found to be similiar to the European-type propolis, having a high flavonoid content. Finally, especially two compounds, 灏?elemene and totarol, were found in Greek samples in quite high amounts that are thought to have important biol. properties. In the experiment, the researchers used many compounds, for example, 3-(2,4-Dimethoxyphenyl)acrylic acid (cas: 6972-61-8Recommanded Product: 6972-61-8).

3-(2,4-Dimethoxyphenyl)acrylic acid (cas: 6972-61-8) 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閳ユ椊 or N閳ユ椊 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.Recommanded Product: 6972-61-8

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

A Unifying Synthesis Approach to the C₁₈-, C₁₉-, and C₂₀-Diterpenoid Alkaloids was written by Kou, Kevin G. M.;Kulyk, Svitlana;Marth, Christopher J.;Lee, Jack C.;Doering, Nicolle A.;Li, Beryl X.;Gallego, Gary M.;Lebold, Terry P.;Sarpong, Richmond. And the article was included in Journal of the American Chemical Society in 2017.Synthetic Route of C6H10O2 This article mentions the following:

The secondary metabolites that comprise the diterpenoid alkaloids are categorized into C18-, C19-, and C20-families depending on the number of contiguous carbon atoms that constitute their central framework. Herein, we detail our efforts to prepare these mols. by chem. synthesis, including a photochem. approach, and ultimately a bioinspired strategy that has resulted in the development of a unifying synthesis of one C18 (weisaconitine D), one C19 (liljestrandinine), and three C20 (cochlearenine, paniculamine, and N-ethyl-1浼?hydroxy-17-veratroyldictyzine) natural products from a common intermediate. 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. 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 feature bent C閳ユ彊閳ユ弲 linkages. In dimethyl ether, the bond angle is 111鎺?and C閳ユ彊 distances are 141 pm. The barrier to rotation about the C閳ユ彊 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.Synthetic Route of C6H10O2

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

Development of a scalable synthesis of SIRT1 modulator macrocycles was written by Tatai, Janos;Molnar, Mark;Villeneuve, Maud;Haberkorn, Laure;Nyerges, Miklos. And the article was included in Heterocycles in 2022.Recommanded Product: 3-Methyl-4-nitroanisole This article mentions the following:

An improved multigram route to key intermediate for macrocyclic SIRT1 modulators was developed. The increasing demand for this key intermediate caused the rerouting of the initial discovery route resulted in increase of overall yield to 8.3% over 8 steps, with the elimination of some tedious chromatog. purifications and the substitution of critical reaction steps, which hindered a feasible scale-up. The key modification was the introduction of the microwave assisted intramol. Suzuki reaction for the macrocyclization step, which provided in a reliable and reproducible manner of the targeted product. This newly developed synthetic access to this first described macrocyclic ring system was capable of ensuring the supply of our medicinal chem. program. In the experiment, the researchers used many compounds, for example, 3-Methyl-4-nitroanisole (cas: 5367-32-8Recommanded Product: 3-Methyl-4-nitroanisole).

3-Methyl-4-nitroanisole (cas: 5367-32-8) 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. 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.Recommanded Product: 3-Methyl-4-nitroanisole

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

Kinetics of oxidation of phenoxyacetic acids by pyridinium hydrobromide perbromide was written by Karunakaran, K.;Elango, K. P.. And the article was included in Journal of Physical Organic Chemistry in 1996.Synthetic Route of C9H10O4 This article mentions the following:

The oxidation of several monosubstituted phenoxyacetic acids by pyridinium hydrobromide perbromide (PHPB) was studied in aqueous acetic acid. The reaction is first order with respect to PHPB. Michaelis-Menten-type kinetics are observed with respect to phenoxyacetic acids. The oxidation of [2,2-²H₂]phenoxyacetic acid exhibits a substantial kinetic isotopic effect. The effect of solvent composition indicates that the transition state is more polar than the reactants. The formation constants of the intermediate phenoxyacetic acid-PHPB complexes and the rates of their decomposition were determined at different temperatures The rates of oxidation of para- and meta-substituted phenoxyacetic acids were correlated with Hammett’s substituent constants The 锜?value is -2璺?9 at 35鎺? The rates of oxidation of ortho-substituted compounds are correlated with Charton’s triparametric equation. A mechanism involving transfer of a hydride ion from the substrate to the oxidant is proposed. In the experiment, the researchers used many compounds, for example, 2-(4-Methoxyphenoxy)acetic acid (cas: 1877-75-4Synthetic Route of C9H10O4).

2-(4-Methoxyphenoxy)acetic acid (cas: 1877-75-4) 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. 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.Synthetic Route of C9H10O4

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

Biomembrane lipids as components of chromatographic phases: comparative chromatography on coated and bonded phases was written by Hanna, M.;De Biasi, V.;Bond, B.;Camilleri, P.;Hutt, A. J.. And the article was included in Chromatographia in 2000.SDS of cas: 5367-32-8 This article mentions the following:

Preparation of biomembrane lipid based stationary phases has been achieved by recycling 1 mM solutions of the appropriate lipid (soybean lecithin phosphatidylcholine, SLPC; phosphatidylcholine, sphingomyelin, phosphatidylethanolamine or phosphatidylserine) in methanol: water (80:20 volume/volume) through reversed-phase (C8) HPLC columns for 18 h at 0.25 mL min^-1. The chromatog. characteristics (retention, peak symmetry and reproducibility and phase stability) have been assessed and compared with two com. available bonded Immobilized Artificial Membrane (IAM) phases (IAM.PC.MG and IAM.PC.DD) by examination of the retention properties of a range of structurally diverse analytes (n = 119). The application of the SLPC phase for prediction of analyte lipophilicity (log Poctanol/water) is shown to be comparable to the IAM.PC.MG and superior to the IAM.PC.DD bonded phases. Cross-phase comparison of analyte retention characteristics on four different lipid phases indicate that such phases may provide a rapid evaluation of analyte-lipid interactions. The dynamic coating methodol. is economically viable for the small laboratory, rapid and reproducible, resulting in phase surfaces which are stable over longer periods of time than those of the com. available bonded phases. In the experiment, the researchers used many compounds, for example, 3-Methyl-4-nitroanisole (cas: 5367-32-8SDS of cas: 5367-32-8).

3-Methyl-4-nitroanisole (cas: 5367-32-8) 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閳ユ椊 or N閳ユ椊 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: 5367-32-8

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

Highly chemoselective acylation of substituted aminophenols with 3-(trimethylacetyl)-1,3-thiazolidine-2-thione was written by Dai, Wei-Min;Cheung, Yuk King;Tang, Kit Wan;Choi, Pui Yiu;Chung, Suet Lam. And the article was included in Tetrahedron in 1995.Recommanded Product: 56619-93-3 This article mentions the following:

A general procedure for chemoselective acylation of substituted aminophenols has been developed. The N-acylated products were prepared in 70-100% yield by treating the aminophenols with 3-(trimethylacetyl)-1,3-thiazolidine-2-thione (1) in refluxing THF. The pivalate esters of 3- and 4-aminophenols could be obtained in 70-94% yield by treating with 1 and NaH. In the experiment, the researchers used many compounds, for example, N-(3-Methoxyphenyl)pivalamide (cas: 56619-93-3Recommanded Product: 56619-93-3).

N-(3-Methoxyphenyl)pivalamide (cas: 56619-93-3) 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 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.Recommanded Product: 56619-93-3

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

A Meta-Selective Copper-Catalyzed C-H Bond Arylation was written by Phipps, Robert J.;Gaunt, Matthew J.. And the article was included in Science (Washington, DC, United States) in 2009.Electric Literature of C12H17NO2 This article mentions the following:

For over a century, chem. transformations of benzene derivatives were guided by the high selectivity for electrophilic attack at the ortho/para positions in electron-rich substrates and at the meta position in electron-deficient mols. The authors have developed a copper-catalyzed arylation reaction that, in contrast, selectively substitutes Ph electrophiles at the aromatic carbon-hydrogen sites meta to an amido substituent. This previously elusive class of transformation is applicable to a broad range of aromatic compounds In the experiment, the researchers used many compounds, for example, N-(3-Methoxyphenyl)pivalamide (cas: 56619-93-3Electric Literature of C12H17NO2).

N-(3-Methoxyphenyl)pivalamide (cas: 56619-93-3) 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. But on the other hand, ethers undergo cleavage by reaction with acids. 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 C12H17NO2

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

Scalable, Divergent Synthesis of a High Aspect Ratio Carbon Nanobelt was written by Bergman, Harrison M.;Kiel, Gavin R.;Handford, Rex C.;Liu, Yi;Tilley, T. Don. And the article was included in Journal of the American Chemical Society in 2021.Formula: C6H10O2 This article mentions the following:

Carbon nanobelts are mols. of high fundamental and technol. interest due to their structural similarity to carbon nanotubes, of which they are mol. cutouts. Despite this attention, synthetic accessibility is a major obstacle, such that the few known strategies offer limited structural diversity, functionality, and scalability. To address this bottleneck, we have developed a new strategy that utilizes highly fused monomer units constructed via a site-selective [2 + 2 + 2] cycloaddition and a high-yielding zirconocene-mediated macrocyclization to achieve the synthesis of a new carbon nanobelt on large scale with the introduction of functional handles in the penultimate step. This nanobelt represents a diagonal cross section of an armchair carbon nanotube and consequently has a longitudinally extended structure with an aspect ratio of 1.6, the highest of any reported nanobelt. This elongated structure promotes solid-state packing into aligned columns that mimic the parent carbon nanotube and facilitates unprecedented host-guest chem. with oligo-arylene guests in nonpolar solvents. In the experiment, the researchers used many compounds, for example, 1,4-Dimethoxy-2-butyne (cas: 16356-02-8Formula: C6H10O2).

1,4-Dimethoxy-2-butyne (cas: 16356-02-8) 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閳ユ椊 or N閳ユ椊 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.Formula: C6H10O2

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

Optical studies on coumarins. II. Ultraviolet absorption of monohydroxycoumarins and derivatives was written by Bohme, Horst;Severin, Theodor. And the article was included in Archiv der Pharmazie und Berichte der Deutschen Pharmazeutischen Gesellschaft in 1957.Application In Synthesis of 3-(2,4-Dimethoxyphenyl)acrylic acid This article mentions the following:

In comparative studies of 4 monohydroxycoumarins, the longwave absorption bands were found to be moved bathochromically by introduction of a hydroxy group in the 6 or 7 position, while the corresponding maximum of 5-and 8-hydroxycoumarins lies at shorter wave lengths. As with coumarin itself 3 bands appear with 5-, 6-, and 8-hydroxycoumarin. 7-Hydroxycoumarin does not produce the medial bands with an inflection at 240 m娓? Dihydroxy-trans-cinnamic acids are optically very similar to their methylated derivatives, but big differences were noted between hydroxycoumarins and dimethoxy-cis-cinnamic acids. In the experiment, the researchers used many compounds, for example, 3-(2,4-Dimethoxyphenyl)acrylic acid (cas: 6972-61-8Application In Synthesis of 3-(2,4-Dimethoxyphenyl)acrylic acid).

3-(2,4-Dimethoxyphenyl)acrylic acid (cas: 6972-61-8) 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 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 3-(2,4-Dimethoxyphenyl)acrylic acid

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