Category: ethers-buliding-blocks

Inter- and intra-molecular organocatalysis of S_N2 fluorination by crown ether: kinetics and quantum chemical analysis was written by Oh, Young-Ho;Yun, Wonhyuck;Kim, Chul-Hee;Jang, Sung-Woo;Lee, Sung-Sik;Lee, Sungyul;Kim, Dong-Wook. And the article was included in Molecules in 2021.Reference of 3929-47-3 This article mentions the following:

We present the intra- and inter-mol. organocatalysis of S_N2 fluorination using CsF by crown ether to estimate the efficacy of the promoter and to elucidate the reaction mechanism. The yields of intramol. S_N2 fluorination of the veratrole substrates are measured to be very small (<1% in 12 h) in the absence of crown ether promoters, whereas the S_N2 fluorination of the substrate possessing a crown ether unit proceeds to near completion (~99%) in 12 h. We also studied the efficacy of intermol. rate acceleration by an independent promoter 18-crown-6 for comparison. We find that the fluorinating yield of a veratrole substrate (leaving group = -OMs) in the presence of 18-crown-6 follows the almost identical kinetic course as that of intramol. S_N2 fluorination, indicating the mechanistic similarity of intra- and inter-mol. organocatalysis of the crown ether for S_N2 fluorination. The calculated relative Gibbs free energies of activation for these reactions, in which the crown ether units act as Lewis base promoters for S_N2 fluorination, are in excellent agreement with the exptl. measured yields of fluorination. The role of the metal salt CsF is briefly discussed in terms of whether it reacts as a contact ion pair or as a “free” nucleophile F^–. In the experiment, the researchers used many compounds, for example, 3-(3,4-Dimethoxyphenyl)propan-1-ol (cas: 3929-47-3Reference of 3929-47-3).

3-(3,4-Dimethoxyphenyl)propan-1-ol (cas: 3929-47-3) 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. But ether is more polar than alkenes. 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.Reference of 3929-47-3

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

Poly(ionic liquid)s with branched side chains: polymer design for breaking the conventional record of ionic conductivity was written by Ikeda, Taichi. And the article was included in Polymer Chemistry in 2021.Application In Synthesis of 2-(2-(2-((Tetrahydro-2H-pyran-2-yl)oxy)ethoxy)ethoxy)ethan-1-ol This article mentions the following:

Poly(ionic liquid)s with non-branched, di-branched, and tri-branched side chains were synthesized using cationic glycidyl triazolyl polymers (GTPs). Based on the analyses of these cationic GTPs, the effects of side-chain branching on phys. properties, such as glass transition temperature and ionic conductivity, were discussed. It was confirmed that the ionic conductivity increased with the degree of side-chain branching. Despite being a high-mol.-weight polymer (1.9 x 10⁶ Da), GTP with tri-branched side chains exhibited a high ionic conductivity of 3.6 x 10^-5 M at 25°C under dry conditions, which is higher than the benchmark value of the conventional poly(ionic liquid)s proposed by Shaplov, Marcilla, and Mecerreyes (3.0 x 10^-5 M at 25°C, dry conditions, mol. weight >10⁵ Da). From the anal. based on the electrode polarization model, the higher ionic conductivity of cationic GTPs with branched side chains can be attributed to their higher conducting ion mobility in the polymer matrix. These results indicate that side-chain branching is effective in breaking the conventional limit of ionic conductivity of poly(ionic liquid)s. 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: 60221-37-6Application In Synthesis of 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. Relative to alcohols, ethers are generally less dense, are less soluble in water, and have lower boiling points. They are relatively unreactive. 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 2-(2-(2-((Tetrahydro-2H-pyran-2-yl)oxy)ethoxy)ethoxy)ethan-1-ol

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

Design, synthesis, and evaluation of dihydropyranopyrazole derivatives as novel PDE2 inhibitors for the treatment of Alzheimer’s disease was written by Zhou, Yan;Li, Jinjian;Yuan, Han;Su, Rui;Huang, Yue;Huang, Yiyou;Li, Zhe;Wu, Yinuo;Luo, Haibin;Zhang, Chen;Huang, Ling. And the article was included in Molecules in 2021.Reference of 57179-35-8 This article mentions the following:

In this study, (R)-LZ77 was obtained as a hit compound with moderate PDE2 inhibitory activity (IC₅₀ = 261.3 nM) using a high-throughput virtual screening method based on mol. dynamics. Then, 28 dihydropyranopyrazole derivatives I [R¹ = H, CH₃O, Cl; R² = H, CH₃, CH₃O, etc.; R³ = H, CH₃, C₆H₅; R⁴ = H, CH₃O, Cl, etc; R⁵ = NH₂, (CH₃)₂N; n = 1, 2, 3] and II [R⁶ = Cl, CF₃; n = 0, 2, 3] were designed and synthesized as PDE2 inhibitors. Among them, compound (+)-I [R¹ = H; R² = CH₃O; R³ = CH₃; R⁴ = CF₃; R⁵ = NH₂; n = 1] was the most potent PDE2 inhibitor, with an IC₅₀ value of 41.5 nM. The mol. docking of PDE2-(+)-I [R¹ = H; R² = CH₃O; R³ = CH₃; R⁴ = CF₃; R⁵ = NH₂; n = 1] revealed that the 4-(trifluoromethyl)benzyloxyl side chain of the compound enters the H-pocket and forms strong hydrophobic interactions with L770/L809/F862, which improves inhibitory activity. The above results may provide insight for further structural optimization of highly potent PDE2 inhibitors and may lay the foundation for their use in the treatment of AD. In the experiment, the researchers used many compounds, for example, 3-Hydroxy-5-methoxybenzaldehyde (cas: 57179-35-8Reference of 57179-35-8).

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

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

Efficient visible light initiated one-pot syntheses of secondary amines from nitro aromatics and benzyl alcohols over Pd@NH₂-UiO-66(Zr) was written by Hao, Mingming;Li, Zhaohui. And the article was included in Applied Catalysis, B: Environmental in 2022.Formula: C8H10O2 This article mentions the following:

Pd@NH₂-UiO-66(Zr), with small-sized Pd nanoparticles encapsulated inside the cavities of NH₂-UiO-66(Zr), was obtained via a double-solvent impregnation followed by a photoreduction process, which shows superior activity for the visible light initiated syntheses of secondary amines from nitro compounds and alcs., via a sequential photocatalytic hydrogenation of nitro compounds/dehydrogenation of alcs., condensation of amines and aldehydes to imines, and the hydrogenation of imines. Simultaneous consumption of photogenerated electrons/holes in the photocatalytic hydrogenation of nitro compounds to amines and dehydrogenation of alcs. to aldehydes promotes the whole reaction. Due to the confinement effect of the cavity and the small-sized Pd nanoparticles, Pd@NH₂-UiO-66(Zr) shows significantly superior performance as compared with Pd/NH₂-UiO-66(Zr), in which larger Pd nanoparticles are deposited on the surface. This study provides an efficient and green strategy for the production of secondary amines and highlights the great potential of using M/MOFs nanocomposites as multifunctional catalysts for light induced one-pot tandem reactions. In the experiment, the researchers used many compounds, for example, (4-Methoxyphenyl)methanol (cas: 105-13-5Formula: C8H10O2).

(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, 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 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.Formula: C8H10O2

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

A new method for the construction of indole nucleus was written by Iwao, Masatomo. And the article was included in Heterocycles in 1994.Recommanded Product: N-(3-Methoxyphenyl)pivalamide This article mentions the following:

Directed lithiation of N-tert-butoxycarbonylanilines I (X = H, Y = H, F, MeO; X = Me, CF₃, MeO, Cl, F, Y = H) and subsequent reaction with 1-tert-butyldimethylsilyl-1-phenylsulfinylethene gave the conjugate addition products which, without isolation, were cyclized to 1-tert-butoxycarbonyl-2-(phenylthio)indolines II under thermal sila-Pummerer reaction conditions. In the experiment, the researchers used many compounds, for example, N-(3-Methoxyphenyl)pivalamide (cas: 56619-93-3Recommanded Product: N-(3-Methoxyphenyl)pivalamide).

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. 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.Recommanded Product: N-(3-Methoxyphenyl)pivalamide

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

Biosynthesis of 4-acetylantroquinonol B in Antrodia cinnamomea via a pathway related to coenzyme Q synthesis was written by Yang, Shang-Han;Lin, Yu-Wei;Chiang, Been-Huang. And the article was included in Biochemical Engineering Journal in 2017.Formula: C9H10O4 This article mentions the following:

The biosynthesis pathway for production of 4-acetylantroquinonol B (4-AAQB) by Antrodia cinnamomea was investigated by adding various precursors to the culture medium. Adding 4-hydroxybenzoic acid (4-HBA) significantly increased the production of 4-AAQB. Since 4-HBA is an intermediate of the shikimate pathway and 4-AAQB and coenzyme Q (CoQ) are similar in structure, we suspected that the pathway for producing 4-AAQB was closely related to the biosynthesis of CoQ. Since the isoprenoid chain of CoQ is synthesized via the mevalonate pathway, we added oleic acid to the culture medium and confirmed that the addition significantly increased the production of 4-AAQB. Furthermore, adding coenzyme Q₀ into the fermentation broth was found to be the most effective way to increase the production of 4-AAQB. We suspect that coenzyme Q₀ forms CoQ, after which CoQ is converted to 4-AAQB via unknown steps. The increase in 4-AAQB production due to the addition of CoQ₁₀ further demonstrated that the biosynthesis pathway of 4-AAQB from A. cinnamomea is closely related to CoQ. In the experiment, the researchers used many compounds, for example, 2,3-Dimethoxy-5-methylcyclohexa-2,5-diene-1,4-dione (cas: 605-94-7Formula: C9H10O4).

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.Formula: C9H10O4

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

Selective removal of ⁹⁰Sr and ⁶⁰Co from aqueous solution using N-aza-crown ether functional poly(NIPAM) hydrogels was written by Deli, Dario;Law, Kathleen;Liu, Zuguang;Crouch, David J.;Livens, Francis R.;Yeates, Stephen G.. And the article was included in Reactive & Functional Polymers in 2012.Name: 1,4,7,10-Tetraoxa-13-azacyclopentadecane This article mentions the following:

The ability of temperature and pH responsive cross-linked poly(NIPAM-co-AAc) hydrogel beads containing covalently bound N-aza-crown ethers to selectively complex ⁹⁰Sr and ⁶⁰Co under competitive and non-competitive conditions is demonstrated using a combination of autoradiog. and scintillation measurements. Due to the presence of copolymerized acrylic acid, which is incorporated to introduce pH responsive behavior as well as acting as the site of covalent attachment of the N-aza-crown ether, the decrease in particle diameter as a function of increasing temperature on going through the LCST of PNIPAM is reduced in the presence of electrolyte. At pH 2 no complexation of either ⁹⁰Sr or ⁶⁰Co was observed At pH 7 the incorporation of acrylic acid under non-competitive conditions results in the ability to complex ca. 90% ⁹⁰Sr and ⁶⁰Co which increases to between 94% and 96% on inclusion of N-aza-crown ether. Under competitive conditions the hydrogels lose the ability to selectively complex ⁹⁰Sr, although the selectivity for ⁶⁰Co was enhanced in the presence of N-aza-crown ether. Subsequent recovery of bound ⁶⁰Co from the hydrogel on lowering to pH 2 was only partially successful, and lead to a decrease in the swelling behavior on readjustment to pH 7. In the experiment, the researchers used many compounds, for example, 1,4,7,10-Tetraoxa-13-azacyclopentadecane (cas: 66943-05-3Name: 1,4,7,10-Tetraoxa-13-azacyclopentadecane).

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

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

In vitro and in silico evaluations of diarylpentanoid series as α-glucosidase inhibitor was written by Leong, Sze Wei;Abas, Faridah;Lam, Kok Wai;Yusoff, Khatijah. And the article was included in Bioorganic & Medicinal Chemistry Letters in 2018.Application In Synthesis of 3-(2,4-Dimethoxyphenyl)acrylic acid This article mentions the following:

A series of thirty-four diarylpentanoids derivatives were synthesized and evaluated for their α-glucosidase inhibitory activity. Eleven compounds were found to significantly inhibit α-glucosidase in which some compounds demonstrated the highest activity with IC₅₀ values ranging from 14.1 to 15.1 μM. Structure-activity comparison shows that multiple hydroxy groups are essential for α-glucosidase inhibitory activity. Meanwhile, 3,4-dihydroxyphenyl and furanyl moieties were found to be crucial in improving α-glucosidase inhibition. Mol. docking analyses further confirmed the critical role of both 3,4-dihydroxyphenyl and furanyl moieties as they bound to α-glucosidase active site in different mode. Overall result suggests that diarylpentanoids with both five membered heterocyclic ring and polyhydroxyphenyl moiety could be a new lead design in the search of novel α-glucosidase inhibitor. 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. Of all the functional groups, ethers are the least reactive ones. Ether bonds are quite stable towards bases, oxidizing agents and reducing agents. 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 In Synthesis of 3-(2,4-Dimethoxyphenyl)acrylic acid

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

Complex Relationship between Side-Chain Polarity, Conductivity, and Thermal Stability in Molecularly Doped Conjugated Polymers was written by Dong, Ban Xuan;Nowak, Christian;Onorato, Jonathan W.;Ma, Tengzhou;Niklas, Jens;Poluektov, Oleg G.;Grocke, Garrett;DiTusa, Mark F.;Escobedo, Fernando A.;Luscombe, Christine K.;Nealey, Paul F.;Patel, Shrayesh N.. And the article was included in Chemistry of Materials in 2021.HPLC of Formula: 111-77-3 This article mentions the following:

Molecularly doped conjugated polymers with polar side chains are an emerging class of conducting materials exhibiting enhanced and thermally stable conductivity Here, we study the electronic conductivity (σ) and the corresponding thermal stability of two polythiophene derivatives comprising oligoethylene glycol side chains: one having oxygen attached to the thiophene ring (poly(3-(methoxyethoxyethoxy)thiophene) (P3MEET)) and the other having a methylene spacer between the oxygen and the thiophene ring (poly(3-(methoxyethoxyethoxymethyl)thiophene) (P3MEEMT)). Thin films were vapor-doped with fluorinated derivatives of tetracyanoquinodimethane (F_nTCNQ, n = 4, 2, 1) to determine the role of dopant strength (electron affinity) in maximum achievable σ. Specifically, when vapor doping with F₄TCNQ, P3MEET achieved a substantially higher σ of 37.1 ± 10.1 S/cm compared to a σ of 0.82 ± 0.06 S/cm for P3MEEMT. Structural characterization using a combination of X-ray and optical spectroscopy reveals that the higher degree of conformational order of polymer chains in the amorphous domain upon doping with F₄TCNQ in P3MEET is a major contributing factor for the higher σ of P3MEET. Addnl., vapor-doped P3MEET exhibited superior thermal stability compared to P3MEEMT, highlighting that the presence of polar side chains alone does not ensure higher thermal stability. Mol. dynamics simulations indicate that the dopant-side-chain nonbond energy is lower in the P3MEET:F₄TCNQ mixture, suggesting more favorable dopant-side-chain interaction, which is a factor in improving the thermal stability of a polymer/dopant pair. Our results reveal that addnl. factors such as polymer ionization energy and side-chain-dopant interaction should be taken into account for the design of thermally stable, highly conductive polymers. In the experiment, the researchers used many compounds, for example, 2-(2-Methoxyethoxy)ethanol (cas: 111-77-3HPLC of Formula: 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 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.HPLC of Formula: 111-77-3

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

Anticotyledon factor: Competitive inhibitors of the action of dihydroconiferyl alcohol in stimulating gibberellic acid-induced lettuce hypocotyl elongation was written by Kamisaka, Seiichiro;Shibata, Kozo. And the article was included in Plant and Cell Physiology in 1977.Recommanded Product: 3-(3,4-Dimethoxyphenyl)propan-1-ol This article mentions the following:

The lettuce cotyledon factor, dihydroconiferyl alc., synergistically enhanced the stimulating effect of gibberellic acid (GA₃) on hypocotyl elongation of decotylized lettuce seedlings. The action of dihydroconiferyl alc. was inhibited by 3-(3,4-dimethoxyphenyl)propanol, 3-(3-hydroxy-4-methoxyphenyl)propionic acid, methyl p-methoxycinnamate, trans-cinnamic acid, p-coumaric acid, ferulic acid, caffeic acid, and synapic acid. Kinetic studies with Lineweaver-Burk plots indicated that these compounds were competitive inhibitors of dihydroconiferyl alc. These inhibitors were termed anticotyledon factors. The action of dihydroconiferyl alc. was not influenced by phenylalanine, tyrosine, p-coumaryl alc., and coniferyl alc. In the experiment, the researchers used many compounds, for example, 3-(3,4-Dimethoxyphenyl)propan-1-ol (cas: 3929-47-3Recommanded Product: 3-(3,4-Dimethoxyphenyl)propan-1-ol).

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. 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.Recommanded Product: 3-(3,4-Dimethoxyphenyl)propan-1-ol

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