Category: ethers-buliding-blocks

A mesoporous NNN-pincer-based metal-organic framework scaffold for the preparation of noble-metal-free catalysts was written by Zhang, Yingmu;Li, Jialuo;Yang, Xinyu;Zhang, Peng;Pang, Jiandong;Li, Bao;Zhou, Hong-Cai. And the article was included in Chemical Communications (Cambridge, United Kingdom) in 2019.Application In Synthesis of 2-(3,5-Dimethoxyphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane This article mentions the following:

Through topol.-guided synthesis, a Zr-based mesoporous MOF was successfully constructed, adopting a β-cristobalite-type structure. The MOF is embedded with well-arranged terpyridine coordination sites for facile post-synthetic metalation, and can be effectively used as a general scaffold for the preparation of noble-metal-free catalysts. For instance, the scaffolded metal@MOF material exhibits highly efficient catalytic activity for alkene epoxidation and arene borylation. In the experiment, the researchers used many compounds, for example, 2-(3,5-Dimethoxyphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (cas: 365564-07-4Application In Synthesis of 2-(3,5-Dimethoxyphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane).

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. 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.Application In Synthesis of 2-(3,5-Dimethoxyphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

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

Biosynthesis of Antroquinonol and 4-Acetylantroquinonol B via a Polyketide Pathway Using Orsellinic Acid as a Ring Precursor in Antrodia cinnamomea was written by Chou, Kevin Chi-Chung;Yang, Shang-Han;Wu, Hsiang-Lin;Lin, Pei-Yin;Chang, Tsu-Liang;Sheu, Fuu;Chen, Kai-Hsien;Chiang, Been-Huang. And the article was included in Journal of Agricultural and Food Chemistry in 2017.Recommanded Product: 2,3-Dimethoxy-5-methylcyclohexa-2,5-diene-1,4-dione This article mentions the following:

Antroquinonol (AQ) and 4-acetylantroquinonol B (4-AAQB), isolated from the submerged fermentation mycelium of Antrodia cinnamomea, have similar chem. backbone to that of coenzyme Q (CoQ). Based on the postulation that biosynthesis of both AQ and 4-AAQB in A. cinnamomea starts from polyketide pathway, the authors cultivated this fungus in a culture medium containing [U-13C]oleic acid, then analyzed the crude extracts of the mycelium using UHPLC-MS. The authors found that AQ and 4-AAQB follow the similar biosynthetic sequences as that of CoQ. Obvious [13C2] fragments on the ring backbone were detected in mass spectrum for [13C2]AQ, [13C2]4-AAQB and their [13C2] intermediates found in this study. The orsellinic acid, formed from acetyl-CoA and malonyl-CoA via polyketide pathway, was found to be a novel benzoquinone ring precursor for AQ and 4-AAQB. The identification of endogenously synthesized farnesylated intermediates allows the authors to postulate the routes of AQ and 4-AAQB biosynthesis in A. cinnamomea. 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: 2,3-Dimethoxy-5-methylcyclohexa-2,5-diene-1,4-dione).

2,3-Dimethoxy-5-methylcyclohexa-2,5-diene-1,4-dione (cas: 605-94-7) 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.Recommanded Product: 2,3-Dimethoxy-5-methylcyclohexa-2,5-diene-1,4-dione

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

Design and synthesis of alkyl substituted pyridino[2,3-D]pyrimidine compounds as PI3Kα/mTOR dual inhibitors with improved pharmacokinetic properties and potent in vivo antitumor activity was written by Liu, Yinyin;Xia, Qinhua;Fang, Lei. And the article was included in Bioorganic & Medicinal Chemistry in 2018.Application of 1009303-77-8 This article mentions the following:

Using pyridino[2,3-D]pyrimidine as the core, total 13 pyridino[2,3-D]pyrimidine derivatives with different alkyl substituents at C2 site have been designed and synthesized to search for novel PI3Kα/mTOR dual inhibitors. Most of the target compounds showed potent mTOR inhibition activity with IC₅₀ values ranging from single to double digit nanomole. Five target compounds exhibited pronounced PI3Kα inhibition activity. In vitro cellular assay indicated that most of the target compounds showed excellent antiproliferative activity, especially I whose potency against SKOV3 was 8-fold higher than the pos. control AZD8055. In vitro metabolic stability study found that I had a comparable stability to that of AZD8055. More importantly, I showed better antitumor activity and pharmacokinetic properties in vivo as compared with AZD8055. In the experiment, the researchers used many compounds, for example, 2-Methoxy-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzenemethanol (cas: 1009303-77-8Application of 1009303-77-8).

2-Methoxy-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzenemethanol (cas: 1009303-77-8) 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. 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.Application of 1009303-77-8

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

Synthesis and anticancer activity of nordihydroguaiaretic acid (NDGA) and analogues was written by McDonald, Russell W.;Bunjobpon, Wilawan;Liu, Tong;Fessler, Sue;Pardo, Olivier E.;Freer, Isabel K. A.;Glaser, Mark;Seckl, Michael J.;Robins, David J.. And the article was included in Anti-Cancer Drug Design in 2001.Category: ethers-buliding-blocks This article mentions the following:

Nordihydroguaiaretic acid (NDGA) is a constituent of the creosote bush Larrea divaricata and is well known to be a selective inhibitor of lipoxygenases. NDGA can also inhibit the platelet derived growth factor receptor and the protein kinase C intracellular signalling family, which both play an important role in proliferation and survival of cancers. Moreover, NDGA induces apoptosis in tumor xenografts. Although it is likely to have several targets of action, NDGA is well tolerated in animals. These encouraging results have prompted interest in the compound for clin. study. However, high concentrations of NDGA are required for efficacy and more potent analogs are required. We have synthesized five analogs of NDGA with different lengths of carbon bridge between the two catechol moieties in order to establish the spacing required for optimum anticancer effect and to compare their activities with NDGA. In order to ascertain if the catechol moieties are essential for anticancer activity, we prepared five analogs of NDGA containing only one hydroxyl group on each aromatic ring. NDGA, its racemic form, and catechol derivatives with five or six carbon atom bridges and the phenol analogs with bridges of three to six carbon atoms all showed similar activity, with IC₅₀ values of âˆ?-5 μM against the H-69 small cell lung cancer cell line. Analogs with shorter or longer bridges were much less active. The most potent analog was the biscatechol with a four-carbon bridge I which was >10 times more active than NDGA and therefore represents a new lead compound in this area. Surprisingly, the tetra-Me ether of this compound was slightly more active than NDGA, but the trihydroxy analog was less active than NDGA. In summary, simplification of the structure of NDGA by removal of the Me groups has produced a new lead compound I, which is >10 times more potent than NDGA as a proliferative inhibitor of H-69 small cell lung cancer cells. In the experiment, the researchers used many compounds, for example, 3-(3,4-Dimethoxyphenyl)propan-1-ol (cas: 3929-47-3Category: ethers-buliding-blocks).

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

Determining Factor on the Polarization Behavior of Magnesium Deposition for Magnesium Battery Anode was written by Tuerxun, Feilure;Yamamoto, Kentaro;Hattori, Masashi;Mandai, Toshihiko;Nakanishi, Koji;Choudhary, Ashu;Tateyama, Yoshitaka;Sodeyama, Keitaro;Nakao, Aiko;Uchiyama, Tomoki;Matsui, Masaki;Tsuruta, Kazuki;Tamenori, Yusuke;Kanamura, Kiyoshi;Uchimoto, Yoshiharu. And the article was included in ACS Applied Materials & Interfaces in 2020.Application of 112-49-2 This article mentions the following:

To clarify the origin of the polarization of magnesium deposition/dissolution reactions, electrochem. measurement, operando soft X-ray absorption spectroscopy (operando SXAS), Raman, and d. functional theory (DFT) techniques are combined to three different electrolytes: magnesium bis(trifluoromethanesulfonyl)amide (Mg(TFSA)₂)/triglyme, magnesium borohydride (Mg(BH₄)₂)/tetrahydrofuran (THF), and Mg(TFSA)₂/2-methyltetrahydrofuran (2-MeTHF). Cyclic voltammetry revealed that magnesium deposition/dissolution reactions occur in Mg(TFSA)₂/triglyme and Mg(BH₄)₂/THF, while the reactions do not occur in Mg(TFSA)₂/2-MeTHF. Raman spectroscopy shows that the [TFSA]^– in the Mg(TFSA)₂/triglyme electrolyte largely does not coordinate to the magnesium ions, while all of the [TFSA]^– in Mg(TFSA)₂/2-MeTHF and [BH₄]^– in Mg(BH₄)₂/THF coordinate to the magnesium ions. In operando SXAS measurements, the intermediate, such as the Mg⁺ ion, was not observed at potentials above the magnesium deposition potential, and the local structure distortion around the magnesium ions increases in all of the electrolytes at the magnesium electrode|electrolyte interface during the cathodic polarization. The DFT calculation and XPS results indicate that the [TFSA]^–, strongly bound to the magnesium ion in the Mg(TFSA)₂/2-MeTHF electrolyte, undergoes reduction decomposition easily, instead of deposition of magnesium metal, which makes the electrolyte inactive electrochem. In the Mg(BH₄)₂/THF electrolyte, because the [BH₄]^– coordinated to the magnesium ions is stable even under the potential of the magnesium deposition, the magnesium deposition is not inhibited by the decomposition of [BH₄]^–. Conversely, because [TFSA]^– is weakly bound to the magnesium ion in Mg(TFSA)₂/triglyme, the reduction decomposition occurs relatively slowly, which allows the magnesium deposition in the electrolyte. In the experiment, the researchers used many compounds, for example, 2,5,8,11-Tetraoxadodecane (cas: 112-49-2Application of 112-49-2).

2,5,8,11-Tetraoxadodecane (cas: 112-49-2) 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, 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.Application of 112-49-2

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

Nitrogen Dioxide-Catalyzed Electrophilic Iodination of Arenes was written by Ren, Yun-Lai;Shang, Huantao;Wang, Jianji;Tian, Xinzhe;Zhao, Shuang;Wang, Qian;Li, Fuwei. And the article was included in Advanced Synthesis & Catalysis in 2013.Computed Properties of C8H9IO This article mentions the following:

Nitrogen oxide (NO₂ nitrogen dioxide) is demonstrated to be an effective catalyst precursor for the iodination of alkoxy-substituted benzene derivatives and naphthalene derivatives Different from transition metal catalysts, nitrogen dioxide can be easily separated from the final products and is free of heavy metal waste. Although the present catalyst precursor is toxic, it does not stain the final products due to its low-boiling character. No other reagents apart from 0.5 equivalent of iodine (I₂), 6.5 mol% nitrogen dioxide and acetonitrile solvent were used in the iodination, and basically all the iodine atoms in the iodine source were transferred to the iodination products, showing that the presented protocol is highly atom-economic and practical. The synthesis of the target compounds was achieved using methoxybenzene, ethoxybenzene, butoxybenzene, (octyloxy)benzene, (tetradecyloxy)benzene, 1-butoxy-2-methyl-benzene, 1,3-dimethoxybenzene, 1-butoxy-3-chlorobenzene, 1,2,3-trimethoxybenzene, 1-methoxynaphthalene as starting materials. Benzofuran, benzothiazole, 2-phenylpyridine, 1-methylimidazole, (ethenyl)benzene, bromobenzene, N,N-diehtylbenzenamine did not provide products in satisfactory yield. Nitriles were obtained in a reaction with tripotassium hexacyanoferrate. In the experiment, the researchers used many compounds, for example, 4-Iodo-1-methoxy-2-methylbenzene (cas: 75581-11-2Computed Properties of C8H9IO).

4-Iodo-1-methoxy-2-methylbenzene (cas: 75581-11-2) 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 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.Computed Properties of C8H9IO

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

Synthesis and structure of 3-isoquinolinols was written by Simchen, Gerhard;Haefner, Manfred. And the article was included in Justus Liebigs Annalen der Chemie in 1975.COA of Formula: C8H9NO3 This article mentions the following:

The isoquinolinols I (X = Cl, Br, or iodine; R = H, Cl, Br, Me, or OMe; R1 = H, Me, or OMe) were prepared by cyclization of 3,4,6-RR1(NC)C6H2CH2COCl in the presence of anhydrous HX. Hydrogenation of I over Pd/C gave I (X = H). The lactam-lactim tautomerism of these compounds was discussed. In the experiment, the researchers used many compounds, for example, 3-Methyl-4-nitroanisole (cas: 5367-32-8COA of Formula: C8H9NO3).

3-Methyl-4-nitroanisole (cas: 5367-32-8) 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. 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.COA of Formula: C8H9NO3

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

Kinetic studies of the transesterification of dimethyl phosphite by alcohols of the guaiacyl and veratryl series was written by Vasil’eva, V. P.;Lykhina, G. G.. And the article was included in Izvestiya Tomskogo Politekhnicheskogo Instituta in 1976.Category: ethers-buliding-blocks This article mentions the following:

The reactivity of alcs. in the title reaction decreased in the order 1-guaiacyl-1-propanol > 1-veratryl-1-propanol (I) > 1-guaiacyl-3-propanol > PhCHEtOH > 1-veratryl-3-propanol (II); the rate constant for I was 15 times that for II. The absence of substituents on the Ph ring deactivated the OH group in the α-position of the propanol side chain. In the experiment, the researchers used many compounds, for example, 3-(3,4-Dimethoxyphenyl)propan-1-ol (cas: 3929-47-3Category: ethers-buliding-blocks).

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. 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).Category: ethers-buliding-blocks

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

Ruthenium-Catalyzed Oxidative Annulation and Hydroarylation of Chromene-3-carboxamides with Alkynes via Double C-H Functionalization was written by Tulichala, R. N. Prasad;Shankar, Mallepalli;Swamy, K. C. Kumara. And the article was included in Journal of Organic Chemistry in 2017.Computed Properties of C6H10O2 This article mentions the following:

Ruthenium-catalyzed oxidative annulation of 2H-chromene-3-carboxamides with alkynes has been achieved by using the directing group nature of amide in the presence of Cu(OAc)₂·H₂O as an oxidant and AgNTf₂ as an additive. This reaction offers a broad substrate scope, and both sym. and unsym. alkynes can be harnessed. High regioselectivity was achieved in the case of unsym. alkynes. In addition, the authors have also accomplished double C-H activation by employing an excess of alkyne, where both annulation and hydroarylation took place regio- and stereoselectively in one pot, with the catalyst playing a dual role. While the first C-H functionalization could involve Ru-N covalent bond, the second C-H functionalization most likely involves Ru-O coordinate bond. The structures of key products, e.g., I, are confirmed by x-ray crystallog. In the experiment, the researchers used many compounds, for example, 1,4-Dimethoxy-2-butyne (cas: 16356-02-8Computed Properties 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. 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.Computed Properties of C6H10O2

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

Synthesis of a cellulose dissolving liquid zwitterion from general and low-cost reagents was written by Sharma, Gyanendra;Kato, Yui;Hachisu, Ayumi;Ishibashi, Kojiro;Ninomiya, Kazuaki;Takahashi, Kenji;Hirata, Eishu;Kuroda, Kosuke. And the article was included in Cellulose (Dordrecht, Netherlands) in 2022.Safety of 2-(2-Methoxyethoxy)ethanol This article mentions the following:

A carboxylate-type liquid zwitterion, OE₂imC₃C, has been recently reported as a unique solvent as a class of ionic liquids with distinctive properties and functions such as cellulose dissolution ability and low toxicity to fermentative microoganisms. Therefore, OE₂imC₃C first enabled successive conversion of biomass to bioethanol in the same reaction pot. However, the reagent, 1-bromo-2-(2-methoxyethoxy)ethane, used for OE₂imC₃C synthesis is expensive and sometimes out of production and thus prevents its industrialization. Here we synthesized OE₂imC₃C from general and low-cost reagents. We also confirmed that the present OE₂imC₃C maintained the distinctive properties and functions because previous literature indicates synthetic procedures affect the properties. The low toxicity and cellulose dissolution ability of the OE₂imC₃C synthesized in this study were equivalent to those of conventional OE₂imC₃C. In addition, OE₂imC₃C is known to have ability to cryopreserve mammalian cells and the OE₂imC₃C synthesized in this study exhibited the ability. In the experiment, the researchers used many compounds, for example, 2-(2-Methoxyethoxy)ethanol (cas: 111-77-3Safety of 2-(2-Methoxyethoxy)ethanol).

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. 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.Safety of 2-(2-Methoxyethoxy)ethanol

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