Category: ethers-buliding-blocks

Practical Electrochemical Iodination of Aromatic Compounds was written by Kataoka, Kazuhide;Hagiwara, Yuji;Midorikawa, Koji;Suga, Seiji;Yoshida, Jun-ichi. And the article was included in Organic Process Research & Development in 2008.Category: ethers-buliding-blocks This article mentions the following:

A practical method for electrochem. iodination of aromatic compounds was developed. The method involves the generation of I⁺ by electrochem. oxidation of I₂ in MeCN using H₂SO₄ as supporting electrolyte followed by the reaction with aromatic compounds The para/ortho selectivity for the reaction of monosubstituted benzenes was significantly improved using dimethoxyethane as cosolvent in the 2nd step. The reaction with highly reactive aromatic compounds gave significant amounts of diiodo compounds in a macrobatch reactor. This problem was solved by fast 1:1 mixing of I⁺ with an aromatic compound using a microflow system consisting of a T-shaped micromixer and a microtube reactor. In the experiment, the researchers used many compounds, for example, 4-Iodo-1-methoxy-2-methylbenzene (cas: 75581-11-2Category: ethers-buliding-blocks).

4-Iodo-1-methoxy-2-methylbenzene (cas: 75581-11-2) 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 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.Category: ethers-buliding-blocks

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

Palladium-Catalyzed Annulation of 2,2′-Diiodobiphenyls with Alkynes: Synthesis and Applications of Phenanthrenes was written by Lin, Yu-De;Cho, Chun-Lung;Ko, Chih-Wei;Pulte, Anna;Wu, Yao-Ting. And the article was included in Journal of Organic Chemistry in 2012.Recommanded Product: 1,4-Dimethoxy-2-butyne This article mentions the following:

A range of phenanthrene derivatives was efficiently synthesized by the palladium-catalyzed annulation of 2,2′-diiodobiphenyls with alkynes. The scope, limitations and regioselectivity of the reaction were investigated. The described method was adopted to synthesize 9,10-dialkylphenanthrenes, sterically overcrowded 4,5-disubstituted phenanthrenes and phenanthrene-based alkaloids. Reactions of highly methoxy-substituted biphenyls with 2-(2-propynyl)pyrrolidine and 2-(2-propynyl)piperidine gave 2-(9-phenanthrylmethyl)pyrrolidines and 2-(9-phenanthrylmethyl)piperidines, resp. The products were transformed to phenanthroindolizidine and phenanthroquinolizidine alkaloids by the Pictet-Spengler reaction. 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. 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 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.Recommanded Product: 1,4-Dimethoxy-2-butyne

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

Regeneration of carbonyl compounds by oxidative cleavage of oximes with NBS in the presence of β-cyclodextrin in water was written by Somi Reddy, M.;Narender, M.;Rama Rao, K.. And the article was included in Synthetic Communications in 2004.Application of 57179-35-8 This article mentions the following:

The conversion of different oximes to the corresponding carbonyl compounds was carried out at room temperature in good to high yields with N-bromosuccinimide in water in the presence of β-cyclodextrin. In the experiment, the researchers used many compounds, for example, 3-Hydroxy-5-methoxybenzaldehyde (cas: 57179-35-8Application of 57179-35-8).

3-Hydroxy-5-methoxybenzaldehyde (cas: 57179-35-8) 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 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 57179-35-8

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

Optimization of catalytic reaction for synthesis of 2-methyl-4-methoxydiphenylamine was written by Cho, Jeong-Woo;Kim, Eun-Seok;Kim, Kiseok;Kim, Seong-Hoon. And the article was included in Kongop Hwahak in 1999.Safety of 3-Methyl-4-nitroanisole This article mentions the following:

Reaction mechanism was elucidated and reaction condition were optimized for the catalytic reaction synthesizing 2-methyl-4-methoxydiphenylamine (MMDPA) which is an intermediate of Fluoran heat-sensitive dyestuff. Reactants consisted of 2-methyl-4-methoxyaniline (MMA), 3-methyl-4-nitroanisole (MNA), and cyclohexanone, and 5 wt% Pd/C was used as a catalyst. Experiments were run in an open slurry reactor equipped with reflux condenser, and products were analyzed by means of GC/MS and NMR. MMDPA yield of 90 mol % could be obtained after reaction time of 8�0 h under the optimal reaction conditions comprising the reaction mass composition of MMA:MNA:cyclohexanone = 1:2:150 based on MMA input of 0.01 gmoles in xylene solvent, reaction temperature of 160°C, and catalyst amount of 0.5 g. It was found that the rate-determining step of overall reaction was dehydrogenation of the intermediate product obtained from condensation of MMA and cyclohexanone. Overall reaction rate and MMDPA yield were enhanced owing to hydrogen transfer reaction by introducing MNA together with MMA in the reaction mass. Excess cyclohexanone in the reaction mass played an important role of promoting the condensation of MMA and cyclohexanone. In the experiment, the researchers used many compounds, for example, 3-Methyl-4-nitroanisole (cas: 5367-32-8Safety of 3-Methyl-4-nitroanisole).

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

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

Catalytic amination in the synthesis of hybrid polymacrocycles comprising porphyrin and azacrown ether moieties was written by Yakushev, Alexei A.;Averin, Alexei D.;Maloshitskaya, Olga A.;Syrbu, Sergei A.;Koifman, Oskar I.;Beletskaya, Irina P.. And the article was included in Mendeleev Communications in 2016.Quality Control of 1,4,7,10-Tetraoxa-13-azacyclopentadecane This article mentions the following:

Pd⁰-catalyzed amination of 3-bromobenzyl-substituted azacrown ethers with propane-1,3-diamine affords the 3-(3-aminopropyl)benzyl derivatives, whose reaction with meso-(bromophenyl)-substituted porphyrins leads to bis- and trismacrocyclic conjugates. In the experiment, the researchers used many compounds, for example, 1,4,7,10-Tetraoxa-13-azacyclopentadecane (cas: 66943-05-3Quality Control of 1,4,7,10-Tetraoxa-13-azacyclopentadecane).

1,4,7,10-Tetraoxa-13-azacyclopentadecane (cas: 66943-05-3) 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).Quality Control of 1,4,7,10-Tetraoxa-13-azacyclopentadecane

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

Iridium-Catalyzed Carbonylative Synthesis of Halogen-Containing Quinolin-2(1H)-ones from Internal Alkynes and Simple Anilines was written by Zhu, Fengxiang;Li, Yahui;Wang, Zechao;Wu, Xiao-Feng. And the article was included in Advanced Synthesis & Catalysis in 2016.COA of Formula: C6H10O2 This article mentions the following:

In this communication, a novel and efficient iridium-catalyzed carbonylative annulation of simple anilines with internal alkynes for the straightforward synthesis of halogen-containing quinolin-2(1H)-ones, e.g., I has been developed. The reaction proceeds without preactivation and directing groups through direct N-H and C-H bond activation with a broad substrate scope and high efficiency. Halogen functional groups can be well tolerated here. Remarkably, this is the first example of an iridium-catalyzed carbonylative C-H activation of anilines. In the experiment, the researchers used many compounds, for example, 1,4-Dimethoxy-2-butyne (cas: 16356-02-8COA of Formula: 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. 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.COA of Formula: C6H10O2

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

Kamlet-Taft solvatochromic parameters for 25 glycol ether solvents and glycol ether aqueous solutions was written by Lagalante, Anthony F.;Wood, Christian;Clarke, Adam M.;Bruno, Thomas J.. And the article was included in Journal of Solution Chemistry in 1998.Product Details of 20324-33-8 This article mentions the following:

The Kamlet-Taft parameters for 25 glycol ethers and their aqueous solutions were measured. Values for the three Kamlet-Taft parameters: the hydrogen-bond donor ability, hydrogen-bond acceptor ability, and the dipolarity/polarizability, as well as the index of refraction, were determined for each pure glycol either and each aqueous glycol solution A correlation matrix between other known solvent parameters and the measured Kamlet-Taft values revealed only one correlation, suggesting that the three measured Kamlet-Taft parameters for the glycol ethers are independent solvent descriptors. Last, trends in the measured Kamlet-Taft values were related to functional group modifications to the basic glycol ether structure. 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: 20324-33-8Product Details 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. 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. 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).Product Details of 20324-33-8

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

Rhodium(NHC)-Catalyzed O-Arylation of Aryl Bromides was written by Kim, Hyun Jin;Kim, Min;Chang, Sukbok. And the article was included in Organic Letters in 2011.Application of 54916-28-8 This article mentions the following:

The first example of the rhodium-catalyzed O-arylation of aryl bromides to give diarylethers, e.g., I, is reported. While the right combination of rhodium species and N-heterocyclic carbene (NHC) offered an effective catalytic system enabling the arylation to proceed, the choice of NHC was determined to be most important. The developed O-arylation protocol has a wide range of substrate scope, high functional group tolerance, and flexibility allowing a complementary route to either N- or O-arylation depending on the choice of NHC. In the experiment, the researchers used many compounds, for example, 1-(4-(4-Methoxyphenoxy)phenyl)ethanone (cas: 54916-28-8Application of 54916-28-8).

1-(4-(4-Methoxyphenoxy)phenyl)ethanone (cas: 54916-28-8) 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. 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 of 54916-28-8

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

Specific features of the reduction of disubstituted amide derivatives of p-tert-butylcalix[4]arene was written by Alekseeva, E. A.;Basok, S. S.;Rakipov, I. M.;Mazepa, A. V.;Gren’, A. I.. And the article was included in Russian Journal of Organic Chemistry in 2013.Formula: C10H21NO4 This article mentions the following:

Regardless of the reducing agent, the reduction at 25°C and at higher temperatures of the amide groups in a large number of p-tert-butylcalix[4]arene derivatives containing amide fragments with different substituents on the nitrogen atoms was accompanied by hydrogenolysis of the C-N bond with formation of the corresponding O-(2-hydroxyethyl)calixarenes and by partial cleavage of the ether bond between the calixarene framework and the substituent to give compounds with a lower degree of substitution. In the experiment, the researchers used many compounds, for example, 1,4,7,10-Tetraoxa-13-azacyclopentadecane (cas: 66943-05-3Formula: C10H21NO4).

1,4,7,10-Tetraoxa-13-azacyclopentadecane (cas: 66943-05-3) 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.Formula: C10H21NO4

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

Structure-based design of novel donepezil-like hybrids for a multi-target approach to the therapy of Alzheimer′s disease was written by Brunetti, Leonardo;Leuci, Rosalba;Carrieri, Antonio;Catto, Marco;Occhineri, Sara;Vinci, Giuseppe;Gambacorta, Lucia;Baltrukevich, Hanna;Chaves, Silvia;Laghezza, Antonio;Altomare, Cosimo Damiano;Tortorella, Paolo;Santos, M. Amelia;Loiodice, Fulvio;Piemontese, Luca. And the article was included in European Journal of Medicinal Chemistry in 2022.Name: 2-(4-Methoxyphenoxy)acetic acid This article mentions the following:

Alzheimer′s disease (AD) is a widespread multifactorial aging-related pathol., which includes cholinergic deficit among its main causes. Following a multi-target design strategy, the structure of the approved drug donepezil was taken as the starting point for generating some new potential multi-functional compounds Therefore, a series of twenty mol. hybrids were synthesized and assayed against three different enzymes, namely the well-established targets acetylcholinesterase (AChE) and butyrylcholinesterase (BChE), and the innovative one fatty acid amide hydrolase (FAAH). In silico studies confirmed the interaction of benzylpiperidine and the benzylpiperazine isostere with the catalytic anionic site (CAS) of AChE, while the aryloxycarbonyl portion appeared to be important for the interaction with the peripheral site (PAS). A QSAR study was carried out on AChE inhibition data, which revealed that the inhibition potency seems to depend upon the length of the spacer and the number of polar atoms. The docking poses of selected compounds within BChE and FAAH were also calculated Furthermore, pharmacokinetics and drug-likeness properties were assessed by chemoinformatic tools. Several piperidine derivatives (in particular compound 10) showed interesting profiles as multi-target directed agents, while the lead piperazine derivative 12 (SON38) was found to be a more potent and selective AChE inhibitor (IC50 = 0.8 nM) than donepezil, besides being able to bind bivalent copper cations (pCu = 7.9 at physiol. pH). Finally, the selected lead compounds (10 and 12, SON38) did not show significant cytotoxicity on SH-SY5Y and HepG2 cells at the highest tested concentration (100 μM) in a MTT assay. In the experiment, the researchers used many compounds, for example, 2-(4-Methoxyphenoxy)acetic acid (cas: 1877-75-4Name: 2-(4-Methoxyphenoxy)acetic acid).

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. 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.Name: 2-(4-Methoxyphenoxy)acetic acid

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