Category: ethers-buliding-blocks

Two-step synthesis of 2-(9-hydroxynonyl)-5,6-dimethoxy-3-methyl-1,4-benzoquinone was written by Wang, Jin;Hu, Xiao;Yang, Jian. And the article was included in Synthesis in 2014.SDS of cas: 605-94-7 This article mentions the following:

2-(9-Hydroxynonyl)-5,6-dimethoxy-3-methyl-1,4-benzoquinone was readily synthesized from com. available 3,4,5-trimethoxytoluene in two steps. First, 2,3-dimethoxy-5-methyl-1,4-benzoquinone (coenzyme Q₀) was obtained in one step by treatment of 3,4,5-trimethoxytoluene with hydrogen peroxide under metal-free conditions, followed by free-radical alkylation with 10-hydroxydecanoic acid in the presence of potassium peroxodisulfate and silver nitrate in a mixed solvent (MeCN-H₂O, 1:1) to afford the title compound in good yields (60%, based on coenzyme Q₀). In the experiment, the researchers used many compounds, for example, 2,3-Dimethoxy-5-methylcyclohexa-2,5-diene-1,4-dione (cas: 605-94-7SDS of cas: 605-94-7).

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. 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: 605-94-7

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

Development of MAP4 Kinase Inhibitors as Motor Neuron-Protecting Agents was written by Bos, Pieter H.;Lowry, Emily R.;Costa, Jonathon;Thams, Sebastian;Garcia-Diaz, Alejandro;Zask, Arie;Wichterle, Hynek;Stockwell, Brent R.. And the article was included in Cell Chemical Biology in 2019.Safety of (4-((4-Methoxybenzyl)oxy)phenyl)boronic acid This article mentions the following:

Disease-causing mutations in many neurodegenerative disorders lead to proteinopathies that trigger endoplasmic reticulum (ER) stress. However, few therapeutic options exist for patients with these diseases. Using an in vitro screening platform to identify compounds that protect human motor neurons from ER stress-mediated degeneration, we discovered that compounds targeting the mitogen-activated protein kinase kinase kinase kinase (MAP4K) family are neuroprotective. The kinase inhibitor URMC-099 (compound 1) stood out as a promising lead compound for further optimization. We coupled structure-based compound design with functional activity testing in neurons subjected to ER stress to develop a series of analogs with improved MAP4K inhibition and concomitant increases in potency and efficacy. Further structural modifications were performed to enhance the pharmacokinetic profiles of the compound 1 derivatives Prostetin/12k emerged as an exceptionally potent, metabolically stable, and blood-brain barrier-penetrant compound that is well suited for future testing in animal models of neurodegeneration. In the experiment, the researchers used many compounds, for example, (4-((4-Methoxybenzyl)oxy)phenyl)boronic acid (cas: 156635-90-4Safety of (4-((4-Methoxybenzyl)oxy)phenyl)boronic acid).

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

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

Synthesis of 9-Phenylacridines via Ortho-Lithiation-Cyclization Sequence* was written by Kinens, A.;Kalnins, T.;Suna, E.. And the article was included in Chemistry of Heterocyclic Compounds (New York, NY, United States) in 2015.COA of Formula: C12H17NO2 This article mentions the following:

Herein, we describe a previously unreported formation of acridines from triarylcarbinols under acidic conditions. Thus, treatment of tertiary alcs. with concentrate aqueous HCl in glacial AcOH at 90° provided 9-phenylacridines in 91-92% yield. The starting tertiary alcs. were prepared by double addition of ortho-lithiated pivaloyl anilines to benzoyl chloride in 76 and 68% yield, resp. Overall, the two-step ortho-lithiation cyclization sequence constitutes a convenient approach to 9-phenylacridines. In the experiment, the researchers used many compounds, for example, N-(3-Methoxyphenyl)pivalamide (cas: 56619-93-3COA of Formula: C12H17NO2).

N-(3-Methoxyphenyl)pivalamide (cas: 56619-93-3) 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. 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.COA of Formula: C12H17NO2

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

Potato tuber cytokinin oxidase/dehydrogenase genes: Biochemical properties, activity, and expression during tuber dormancy progression was written by Suttle, Jeffrey C.;Huckle, Linda L.;Lu, Shunwen;Knauber, Donna C.. And the article was included in Journal of Plant Physiology in 2014.Recommanded Product: 605-94-7 This article mentions the following:

The enzymic and biochem. properties of the proteins encoded by five potato cytokinin oxidase/dehydrogenase (CKX)-like genes functionally expressed in yeast and the effects of tuber dormancy progression on StCKX expression and cytokinin metabolism were examined in lateral buds isolated from field-grown tubers. All five putative StCKX genes encoded proteins with in vitro CKX activity. All five enzymes were maximally active at neutral to slightly alk. pH with 2,6-dichloro-indophenol as the electron acceptor. In silico analyses indicated that four proteins were likely secreted. Substrate dependence of two of the most active enzymes varied; one exhibiting greater activity with isopentenyl-type cytokinins while the other was maximally active with cis-zeatin as a substrate. [³H]-isopentenyl-adenosine was readily metabolized by excised tuber buds to adenine/adenosine demonstrating that CKX was active in planta. There was no change in apparent in planta CKX activity during either natural or chem. forced dormancy progression. Similarly although expression of individual StCKX genes varied modestly during tuber dormancy, there was no clear correlation between StCKX gene expression and tuber dormancy status. Thus although CKX gene expression and enzyme activity are present in potato tuber buds throughout dormancy, they do not appear to play a significant role in the regulation of cytokinin content during tuber dormancy progression. In the experiment, the researchers used many compounds, for example, 2,3-Dimethoxy-5-methylcyclohexa-2,5-diene-1,4-dione (cas: 605-94-7Recommanded Product: 605-94-7).

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. 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).Recommanded Product: 605-94-7

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

Hypocholesterolemic and choleretic effects of three dimethoxycinnamic acids in relation to 2,4,5-trimethoxycinnamic acid in rats fed with a high-cholesterol/cholate diet was written by Serna, Manuel;Wong-Baeza, Carlos;Santiago-Hernandez, Juan-Carlos;Baeza, Isabel;Wong, Carlos. And the article was included in Pharmacological Reports in 2015.Application of 6972-61-8 This article mentions the following:

2,4,5-Trimethoxycinnamic acid (2,4,5-TMC) is the major and non-toxic metabolite of α-asarone, which retains hypocholesterolemic and choleretic activities. We compared the activities of 2,4,5-TMC with those of 2,4-dimethoxycinnamic acid (2,4-DMC), 3,4-DMC and 3,5-DMC, to understand the role of the methoxyls on carbons 2, 4 and 5 on the pharmacol. properties of these compounds The methoxycinnamic acids were administered to high-cholesterol/cholate-fed rats. We measured bile flow, and quantified bile acids, phospholipids and cholesterol in bile, and cholesterol and cholesterol-lipoproteins in serum. The inhibition of HMG-CoA reductase by the methoxycinnamic acids was evaluated in vitro. The four methoxycinnamic acids decreased serum cholesterol, without affecting the concentration of HDL-cholesterol. 2,4,5-TMC produced the highest decrease in LDL-cholesterol, 73.5%, which exceeds the range of statins (20-40%), and produced the highest inhibition of the activity of HMG-CoA reductase. 3,4-DMC produced the highest increase in bile flow, bile acids and phospholipids concentrations, and reduction in bile cholesterol, which led to a decrease in the biliary cholesterol saturation index.2,4,5-TMC (which has three methoxyls) had the highest hypocholesterolemic activity, while 3,4-DMC, which lacks the methoxyl in carbon 2 but conserves the two other methoxyls in an adjacent position, had the highest choleretic activity and a probable cholelitholytic activity. In methoxycinnamic acids with two methoxyls in non-adjacent positions (2,4-DMC and 3,5-DMC), the hypocholesterolemic and choleretic activities were not as evident. 2,4,5-TMC and 3,4-DMC, which did not cause liver damage during the treatment period, should be further explored as a hypocholesterolemic and choleretic compounds in humans. In the experiment, the researchers used many compounds, for example, 3-(2,4-Dimethoxyphenyl)acrylic acid (cas: 6972-61-8Application of 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. 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 6972-61-8

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

Mild and regioselective iodination of electron-rich aromatics with N-iodosuccinimide and catalytic trifluoroacetic acid was written by Castanet, Anne-Sophie;Colobert, Francoise;Broutin, Pierre-Emmanuel. And the article was included in Tetrahedron Letters in 2002.SDS of cas: 75581-11-2 This article mentions the following:

A variety of aromatic compounds substituted with methoxy or Me groups were regioselectively iodinated with N-iodosuccinimide and catalytic HO₂CCF₃ with excellent yields under mild conditions and short reaction times. In the experiment, the researchers used many compounds, for example, 4-Iodo-1-methoxy-2-methylbenzene (cas: 75581-11-2SDS of cas: 75581-11-2).

4-Iodo-1-methoxy-2-methylbenzene (cas: 75581-11-2) 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.SDS of cas: 75581-11-2

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

The Synthesis of Benzofulvenes through Palladium-Catalyzed Sequential Three-Component Reactions was written by Zhou, Bo;Wu, Zhuo;Qi, Weixin;Sun, Xueliang;Zhang, Yanghui. And the article was included in Advanced Synthesis & Catalysis in 2018.Recommanded Product: 75581-11-2 This article mentions the following:

An approach for the synthesis of benzofulvenes was developed through palladium-catalyzed sequential three-component reactions. The reactions likely involved C,C-palladacycles as the key intermediates. The palladacycles were generated through cascade reactions of aryl halides and alkynes, and then reacted with CH₂Br₂ to form benzofulvenes as the final products. In the experiment, the researchers used many compounds, for example, 4-Iodo-1-methoxy-2-methylbenzene (cas: 75581-11-2Recommanded Product: 75581-11-2).

4-Iodo-1-methoxy-2-methylbenzene (cas: 75581-11-2) 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. 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.Recommanded Product: 75581-11-2

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

Photosynthetic Bioelectronic Sensors for Touch Perception, UV-Detection, and Nanopower Generation: Toward Self-Powered E-Skins was written by Ravi, Sai Kishore;Wu, Tingfeng;Udayagiri, Vishnu Saran;Vu, Xuan Minh;Wang, Yanan;Jones, Michael R.;Tan, Swee Ching. And the article was included in Advanced Materials (Weinheim, Germany) in 2018.Synthetic Route of C9H10O4 This article mentions the following:

Energy self-sufficiency is an inspirational design feature of biol. systems that fulfills sensory functions. Plants such as the “touch-me-not” and “Venus flytrap” not only sustain life by photosynthesis, but also execute specialized sensory responses to touch. Photosynthesis enables these organisms to sustainably harvest and expend energy, powering their sensory abilities. Photosynthesis therefore provides a promising model for self-powered sensory devices like electronic skins (e-skins). While the natural sensory abilities of human skin have been emulated in man-made materials for advanced prosthetics and soft-robotics, no previous e-skin has incorporated phototransduction and photosensory functions that could extend the sensory abilities of human skin. A proof-of-concept bioelectronic device integrated with natural photosynthetic pigment-proteins is presented that shows the ability to sense not only touch stimuli (down to 3000 Pa), but also low-intensity UV radiation (down to 0.01 mW cm^-2) and generate an elec. power of ≈260 nW cm^-2. The scalability of this device is demonstrated through the fabrication of flexible, multipixel, bioelectronic sensors capable of touch registration and tracking. The polysensory abilities, energy self-sufficiency, and addnl. nanopower generation exhibited by this bioelectronic system make it particularly promising for applications like smart e-skins and wearable sensors, where the photogenerated power can enable remote data transmission. In the experiment, the researchers used many compounds, for example, 2,3-Dimethoxy-5-methylcyclohexa-2,5-diene-1,4-dione (cas: 605-94-7Synthetic Route of C9H10O4).

2,3-Dimethoxy-5-methylcyclohexa-2,5-diene-1,4-dione (cas: 605-94-7) 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.Synthetic Route of C9H10O4

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

Efficient synthesis of 6-(hetero)arylthieno[3,2-b]pyridines by Suzuki-Miyaura coupling. Evaluation of growth inhibition on human tumor cell lines, SARs and effects on the cell cycle was written by Queiroz, Maria-Joao R. P.;Calhelha, Ricardo C.;Vale-Silva, Luis A.;Pinto, Eugenia;Lima, Raquel T.;Vasconcelos, M. Helena. And the article was included in European Journal of Medicinal Chemistry in 2010.Synthetic Route of C14H21BO4 This article mentions the following:

A wide variety of new bi(hetero)aryl derivatives of the thieno[3,2-b]pyridine skeleton was obtained in high to excellent yields (65-91%) by Suzuki-Miyaura cross-coupling of the Me 3-amino-6-bromothieno[3,2-b]pyridine-2-carboxylate, recently reported by us, with aryl or heteroaryl pinacolboranes or potassium trifluoroborates. The coupling products obtained were evaluated for their growth inhibitory effect on three human tumor cell lines, representing different tumor models, MCF-7 (breast adenocarcinoma), A375-C5 (melanoma) and NCI-H460 (non-small cell lung cancer). Some of the compounds showed an interesting activity against the tested cell lines, with GI₅₀ values in the μM range, and it was possible to establish some structure-activity relationships (SARs). Several compounds presented GI₅₀ values below 15 μM, particularly a bithiophene and an o-aniline thienopyridine derivative The first presented selectivity for MCF-7 and NCI-H460 cell lines, with very low GI₅₀ values (0.7-1.0 μM), while the latter was active against the three cell lines tested in this study, also presenting very low GI₅₀ values (2.5-4.2 μM). The effect of these two compounds on cell cycle progression was analyzed in the NCI-H460 cell line. Results showed that both compounds interfered with the normal cell cycle distribution. In the experiment, the researchers used many compounds, for example, 2-(3,5-Dimethoxyphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (cas: 365564-07-4Synthetic Route of C14H21BO4).

2-(3,5-Dimethoxyphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (cas: 365564-07-4) 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.Synthetic Route of C14H21BO4

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

Formation of organometallic species from complexes of N-phenylaza-crown ether conjugates with lead cations in CID-MS/MS conditions was written by Franski, Rafal;Ogorek, Katarzyna;Gierczyk, Blazej. And the article was included in International Journal of Mass Spectrometry in 2017.Safety of 1,4,7,10-Tetraoxa-13-azacyclopentadecane This article mentions the following:

Gas phase decomposition of the ions [M + PbNO₃]⁺ (M stands for fluoro-substituted N-nitrophenylaza-crown ether conjugate), has been studied by the electrospray ionization-collision induced dissociation-tandem mass spectrometry (ESI-CID-MS/MS). The conjugates containing hydrogen atom at ortho position to the crown moiety, form abundant fragment ions which can be assigned as complexes of deprotonated conjugates and lead cation, thus the ions [M – H + Pb]⁺ (fragment ions formed as a result of HNO₃ loss). Interaction between the nitro group (present at the second ortho position to the crown moiety) and the metal cation affects the formation of fragment ion [M – H + Pb]⁺ (but does not prevent its formation). Ions [M – H + Pb]⁺ are very rare example of the organometallic species (containing metal-carbon bond), in which metal cation is also complexed by crown ether moiety. In the experiment, the researchers used many compounds, for example, 1,4,7,10-Tetraoxa-13-azacyclopentadecane (cas: 66943-05-3Safety of 1,4,7,10-Tetraoxa-13-azacyclopentadecane).

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

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