Category: ethers-buliding-blocks

Naturally occurring compounds related to phenalenone. Part 9. Synthesis of 8,9-dihydro-1,2,3,6-tetrahydroxy-4,8,8,9-tetramethylphenaleno[1,2-b]furan-7-one and 8,9-dihydro-1,4,5,6-tetrahydroxy-3,8,8,9-tetramethylphenaleno[1,2-b]furan-7-one was written by Halton, David D.;Morrison, George A.. And the article was included in Journal of Chemical Research, Synopses in 1979.Category: ethers-buliding-blocks This article mentions the following:

The title furanones (I; R = H, R¹ = Me, R² = R³ = OH; R = R¹ = OH, R² = Me, R³ = H, resp.) were prepared in 9 steps from 3,4,5-(MeO)₃C₆H₂CH₂CHO (II), for which an improved synthesis was developed. The key intermediate in the syntheses was the naphthalene III, obtained in 9.4% overall yield. In the experiment, the researchers used many compounds, for example, 3-Hydroxy-5-methoxybenzaldehyde (cas: 57179-35-8Category: ethers-buliding-blocks).

3-Hydroxy-5-methoxybenzaldehyde (cas: 57179-35-8) 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―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.Category: ethers-buliding-blocks

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

Natural Hyperbolic Dispersion with Anisotropic Epsilon-Near-Zero and Epsilon-Near-Pole in Squaraine Molecular Film was written by Kim, Minjae;Choi, Kyu Ri;Lee, Yeon Ui;Heinrich, Benoit;Ko, Soo Young;Mathevet, Fabrice;Ribierre, Jean-Charles;D′Aleo, Anthony;Wu, Jeong Weon;Placide, Virginie. And the article was included in Advanced Optical Materials in 2021.SDS of cas: 111-77-3 This article mentions the following:

Epsilon-near-zero (ENZ) optical material has been employed in a number of novel linear and nonlinear optical applications, owing to the vanishing polarization upon an incident optical wave. In a uniaxial medium possessing hyperbolic energy-momentum dispersion of optical wave, ENZ can take place at ordinary and extraordinary permittivities. Organic thin films presenting a lamellar structure have been reported to exhibit a transverse neg. hyperbolic dispersion with ENZ at ordinary permittivity. Here, organic thin film with ENZ at extraordinary permittivity is demonstrated. Newly synthesized polymethine dye (i.e., squaraine indolenine triethyleneglycol mol.) self-organizes to form a layered structure in a pristine film, and both transverse neg. and pos. hyperbolic dispersions are observed at visible wavelengths. Anal. of tens-nanometer-thick pristine film shows that both ENZ and epsilon-near-pole (ENP) occur at longitudinal as well as transverse component of dielec. permittivity. Optical characterization of squaraine pristine film is presented, and the importance of transverse pos. hyperbolic dispersion in such monolithic thin film is discussed. In the experiment, the researchers used many compounds, for example, 2-(2-Methoxyethoxy)ethanol (cas: 111-77-3SDS of cas: 111-77-3).

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

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

Synthesis of substituted 2-[bis(4-hydroxyphenyl)methyl]pyridines was written by Schulz, Otto Erich;Fedders, Soenke. And the article was included in Archiv der Pharmazie (Weinheim, Germany) in 1977.Safety of (6-Methoxypyridin-2-yl)methanol This article mentions the following:

The title compounds I (R = H, R1 = 5-Me, 4-Me, 3-Me, 4-OMe, 4-Cl, 4-OCH2Ph, 4-OH, 6-OMe; R = Ac, R1 = 3-Me, 4-OMe, 4-Cl) were prepared by treating 2-methylpyridine N-oxides with Ac2O, hydrolyzing 2-acetoxymethylpyridines, oxidizing 2-hydroxymethylpyridines with SeO2, and treating 2-formylpyridines with PhOH in the presence of H2SO4. In the experiment, the researchers used many compounds, for example, (6-Methoxypyridin-2-yl)methanol (cas: 63071-12-5Safety of (6-Methoxypyridin-2-yl)methanol).

(6-Methoxypyridin-2-yl)methanol (cas: 63071-12-5) 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. 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.Safety of (6-Methoxypyridin-2-yl)methanol

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

A novel and direct synthesis of chroman derivatives using a hypervalent iodine(III) reagent was written by Hamamoto, Hiromi;Hata, Kayoko;Nambu, Hisanori;Shiozaki, Yukiko;Tohma, Hirofumi;Kita, Yasuyuki. And the article was included in Tetrahedron Letters in 2004.SDS of cas: 3929-47-3 This article mentions the following:

The direct aromatic carbon-oxygen bond-formation reaction was described and the novel and simple synthetic method for chroman derivatives involving aromatic cation radical intermediates was developed using the hypervalent iodine(III) reagent, phenyliodine(III) bis(trifluoroacetate) (PIFA). In the experiment, the researchers used many compounds, for example, 3-(3,4-Dimethoxyphenyl)propan-1-ol (cas: 3929-47-3SDS of cas: 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. 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.SDS of cas: 3929-47-3

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

Amidines in the Diels-Alder synthesis was written by Martinez, Joaquin Royo. And the article was included in Rev. real. acad. cienc. exact. fís. y nat. Madrid in 1952.SDS of cas: 51488-33-6 This article mentions the following:

Several amidines were prepared as follows. CH₂(OH)CH₂Cl + NaCN → CH₂(OH)CH₂CN (I), b₁₅ 110° (84%); I + finely divided Al (hydroquinone to eliminate polymerization) → CH₂:CHCN (II), b. 77.6-79.0° (69.3%); II + EtOH (distilled from Na), saturated with gaseous HCl → CH₂:CHC(:NH₂Cl)OEt (III), m. 104-4.5° (decomposition), stable in bottles with airtight stoppers; III in absolute EtOH + NH₃ in absolute EtOH (3 hr. agitation, followed by standing 2 days) → CH₂:CHC(:NH₂Cl)NH₂. Similarly, vanillin + NaOH + MeI → (MeO)₂C₆H₃CHO → (MeO)₂C₆H₃CH:NOH → (MeO)₂C₆H₃CN, m. 67°, → (MeO)₂C₆H₃C(:NH₂Cl)OEt, m. 141° (decomposition) → (MeO)₂C₆H₃C(:NH₂Cl)NH₂, m. 237°. Piperonal → oxime, m. 110°, → piperonylonitrile, m. 94.5°, → Et piperonylimidate-HCl, m. 122-3°, → piperonylamidine-HCl, m. 238° (decomposition) → piperonylamidine, m. 167°, → picrate, m. 257°. PhCN → m-O₂NC₆H₄CN, m. 117.5°, → m-O₂NC₆H₄C(:NH₂Cl)OEt → m-O₂NC₆H₄(:NH₂Cl)NH₂, m. 250° (decomposition). There was no reaction comparable to a Diels-Alder, between these amidines and styrene, anethole, or maleic anhydride. MeNO₂ and CH₂(OH)CN, used as solvents, were prepared by the decarboxylation of CH₂(NO₂)CO₂H and by the addition of HCN to CH₂O, resp. In the experiment, the researchers used many compounds, for example, 3,4-Dimethoxybenzimidamide hydrochloride (cas: 51488-33-6SDS of cas: 51488-33-6).

3,4-Dimethoxybenzimidamide hydrochloride (cas: 51488-33-6) 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. 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.SDS of cas: 51488-33-6

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

Synthesis of analogs of the Gwt1 inhibitor manogepix (APX001A) and in vitro evaluation against Cryptococcus spp was written by Trzoss, Michael;Covel, Jonathan A.;Kapoor, Mili;Moloney, Molly K.;Soltow, Quinlyn A.;Webb, Peter J.;Shaw, Karen Joy. And the article was included in Bioorganic & Medicinal Chemistry Letters in 2019.Formula: C14H15BO4 This article mentions the following:

Fosmanogepix (APX001) is a first-in-class prodrug mol. that is currently in Phase 2 clin. trials for invasive fungal infections. The active moiety manogepix (APX001A) inhibits the novel fungal protein Gwt1. Gwt1 catalyzes an early step in the GPI anchor biosynthesis pathway. Here we describe the synthesis and evaluation of 292 new and 24 previously described analogs that were synthesized using a series of advanced intermediates to allow for rapid analoging. Several compounds demonstrated significantly (8- to 32-fold) improved antifungal activity against both Cryptococcus neoformans and C. gattii as compared to manogepix. Further in vitro characterization identified three analogs with a similar preliminary safety and in vitro profile to manogepix and superior activity against Cryptococcus spp. In the experiment, the researchers used many compounds, for example, (4-((4-Methoxybenzyl)oxy)phenyl)boronic acid (cas: 156635-90-4Formula: C14H15BO4).

(4-((4-Methoxybenzyl)oxy)phenyl)boronic acid (cas: 156635-90-4) 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 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: C14H15BO4

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

Ru-Catalyzed Hydrogenolysis of Lignin: Base-Dependent Tunability of Monomeric Phenols and Mechanistic Study was written by Li, Helong;Song, Guoyong. And the article was included in ACS Catalysis in 2019.Electric Literature of C11H16O3 This article mentions the following:

Substantial attention has been given to depolymerization of lignin into monomeric phenols in recent years because lignin is a renewable and CO₂-natural aromatic resource. Recent results indicated that the base can shift the selectivity from C3-fragmented phenols to C2-fragmented phenols partially in transition metal-catalyzed lignin hydogenolysis, while reaction mechanisms have remained elusive. Using a series of dimeric, trimeric, and polymeric β-O-4 lignin mimics, as well as their deuterated analogs, we now report an in-depth exptl. study on the mechanism of Ru/C-catalyzed hydogenolysis lignin. Exptl. evidence based on substrate probes, reactivity examination of possible intermediates, and isotopic labeling experiments confirmed that the reported pathways, such as enol ether generated via α,β-dehydration reaction or C_α carbonyl compounds generated via dehydrogenation or consecutive C_β-O and C_γ-OH bonds hydrogenolysis, are irrelevant to current reactions. For C3-fragmented phenols with Ru/C catalyst under neutral condition, we deduced that the monolignol such as coniferyl alc. is formed primarily through a concerted hydrogenolysis process, where C_α-O and C_β-O bonds are ruptured synchronously. For C2-fragmented phenols generated by the combination of Ru/C and Cs₂CO₃, the reaction should start from quinone methide specie generated from the dehydration (or demethanolization) reaction between phenolic proton and C_α-OH (or C_α-OMe). The followed deprotonation of C_γ-OH and the coordination of oxygen with Ru results in a Ru specie, which undergoes C_β-H, C_β-O, and C_β-C_γ bonds cleavage to release 4-vinylphenol. In the case of Ru/C-catalyzed hydrogenolysis of an enzymic mild acidolysis lignin (EMAL) derived from birch tree, the effects of some key parameters such as temperature, reaction time, as well as the type and dosage of base were also examined in terms of monomer yields and selectivity. We found the formation of C2-phenols is a base-dependent process, which is in line with the proposed mechanism. Under optimized conditions, a high proportion of C2-phenols (44%) could be obtained with 26.6 weight % total monomers yield. In the experiment, the researchers used many compounds, for example, 3-(3,4-Dimethoxyphenyl)propan-1-ol (cas: 3929-47-3Electric Literature of C11H16O3).

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

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

High hypolipidemic activity of saturated side-chain α-asarone analogs was written by Cruz, Adriana;Garduno, Leticia;Salazar, Maria;Martinez, Elizdath;Diaz, Francisco;Chamorro, German;Tamariz, Joaquin. And the article was included in Medicinal Chemistry Research in 2001.SDS of cas: 3929-47-3 This article mentions the following:

With the aim of evaluating the pharmacophore potential of the side chain of α-asarone regarding its high hypolipidemic activity, α-asarone analogs (I) were evaluated pharmacol. For I, with a variable-size side chain, significant decreases in serum cholesterol, LDL-cholesterol, and triglyceride levels and significant increases in HDL-cholesterol levels were observed in mice. I were even more active than α-asarone in reducing cholesterol. The results suggested that the length and saturated character of the side chain seem to be a key feature in improving hypolipidemic activity of I. In the experiment, the researchers used many compounds, for example, 3-(3,4-Dimethoxyphenyl)propan-1-ol (cas: 3929-47-3SDS of cas: 3929-47-3).

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

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

Influence of hydrogen bond on the mesomorphic behaviour in urethane based liquid crystalline compounds: Experimental and computer simulation study was written by Korkmaz, Burak;Agtas, Sinem;Sutay, Berkay;Yildirim, Erol;Yilgor, Iskender;Yurtsever, Mine;Senkal, B. Filiz;Gursel, Yesim. And the article was included in Journal of Molecular Liquids in 2020.Product Details of 111-77-3 This article mentions the following:

We present a combined exptl. and theor. study on the novel hydrogen-bonded liquid crystalline complex (UR-LC11) exhibiting both nematic and smectic phases upon cooling. The complex was prepared by mixing 2-(2-methoxyethoxy)ethylbutyl carbamate (UR) as H-bond acceptor with calamitic mesogen 4′-((11-hydroxyundecyl)oxy)-[1,1′-biphenyl]-4-carbonitrile (LC11) as H-bond donor. The complex was characterized by FTIR technique and its liquid crystalline properties were studied by differential scanning calorimetry (DSC) and polarized optical microscope (POM). The exptl. IR spectra were compared with theor. obtained IR spectra by D. Functional Theory (DFT) to suggest the structure of hydrogen-bonded liquid crystal (LC). The mol. dynamics (MD) simulations were performed to understand the impact of hydrogen bonding on the mesomorphic behavior of the complex and the temperature dependency of the transitions between the mesophases. We determined that UR-LC11 is a stable H-bond acceptor/donor type complex and a single H-bond forms between the carbonyl oxygen atom of the amide moiety of UR and the hydrogen atom of the terminal hydroxyl group of the LC11. Although LC11 is present only in nematic liquid crystalline form, the new complex displayed both nematic and smectic phases during cooling. The reason for the two distinctive LC phases was explained by the presence of hydrogen bond interactions, which provides structural flexibility. Besides, H-bond maintains uniaxial rod shape of the mol. to promote self-assembly behavior and induces positional ordering in the smectic phase. The enhancement in the self-assembly of the H-bonded chains in the complex is reflected in the increased ΔH_fusion values. Due to the intermol. π-π interactions of the Ph rings and the formation of strong dipoles on the backbone, especially at the cyanobiphenyl end of the chains, the long-range directional order of the dipoles along their long axes are preserved at elevated temperatures and nematic to isotropic phase transition is observed at around 370 K both exptl. and theor. 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. 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.Product Details of 111-77-3

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

Mo-Based Oxidizers as Powerful Tools for the Synthesis of Thia- and Selenaheterocycles was written by Franzmann, Peter;Beil, Sebastian B.;Schollmeyer, Dieter;Waldvogel, Siegfried R.. And the article was included in Chemistry – A European Journal in 2019.Reference of 3929-47-3 This article mentions the following:

A highly efficient synthetic protocol for the synthesis of thia- and selenaheterocycles has been developed. By employing a MoCl₅-mediated intramol. dehydrogenative coupling reaction, a broad variety of structural motifs was isolated in yields up to 94 % [e.g., bis(2-(3,4-dimethoxyphenyl)ethyl) disulfide → 4,5-dimethoxybenzothiophene (65 %) in the presence of MoCl₅ + TiCl₄ (2 equiv)]. The electrophilic key transformation is tolerated by several labile moieties like halides and tertiary alkyl groups. Due to the use of disulfide or diselenide precursors, a high atom efficiency was achieved. 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. 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).Reference of 3929-47-3

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