Month: February 2023

Metal-Free Photoinduced Transformation of Aryl Halides and Diketones into Aryl Ketones was written by Yao, Qiuli;Liu, Wenbo;Liu, Peng;Ren, Linjing;Fang, Xuehong;Li, Chao-Jun. And the article was included in European Journal of Organic Chemistry in 2019.SDS of cas: 75581-11-2 This article mentions the following:

The acylation of aryl halides to prepare aryl ketones without metal catalyst represents an important yet challenging topic towards more sustainable ketone synthesis. A simple and efficient metal-free protocol for the acylation of aryl halides with diketone under the irradiation of light utilizing N-methylpiperidine as base under an air atm. is described. This reaction can tolerate a wide range of functional groups and the corresponding ketones can be obtained in modest to good yields. 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. 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.SDS of cas: 75581-11-2

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

Gold(I)-catalyzed addition of carboxylic acids to internal alkynes in aqueous medium was written by Gonzalez-Liste, Pedro J.;Garcia-Garrido, Sergio E.;Cadierno, Victorio. And the article was included in Organic & Biomolecular Chemistry in 2017.HPLC of Formula: 16356-02-8 This article mentions the following:

The efficient hydro-oxycarbonylation of sym. and unsym. internal alkynes RCCR¹ (R = R¹ = CH₂CH₃; R = C₆H₅, R¹ = CH₃; R = CH₃, R¹ = C(O)₂CH₂CH₃, etc.) with carboxylic acids R²C(O)₂H [R² = C₆H₅, (CH₂)₅CH₃, cyclohexyl, etc.] in water at 60 闁硅櫣鐓? employs the catalytic system [AuCl(PPh₃)]/AgOAc (5 mol%) has been reported. This simple and eco-friendly protocol allows for the synthesis of a wide variety of trisubstituted enol esters (Z)-I and (Z)-II in high yields and with complete Z-stereoselectivity. The use of microwave irradiation as an alternative energy source has also been evaluated. In the experiment, the researchers used many compounds, for example, 1,4-Dimethoxy-2-butyne (cas: 16356-02-8HPLC of Formula: 16356-02-8).

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. 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.HPLC of Formula: 16356-02-8

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

A Lewis acid-promoted cyclization of ethenetricarboxylate derivative aromatic compounds. Novel syntheses of oxindoles and benzofuranones via Friedel-Crafts intramolecular Michael addition was written by Yamazaki, Shoko;Morikawa, Satoshi;Iwata, Yuko;Yamamoto, Machiko;Kuramoto, Kaori. And the article was included in Organic & Biomolecular Chemistry in 2004.Name: 3-(3,4-Dimethoxyphenyl)propan-1-ol This article mentions the following:

A cyclization reaction of ethenetricarboxylate derivative aromatic compounds, in the presence of various Lewis acids, gave benzo-annulated cyclic compounds such as oxindoles, e.g., I, and benzofuranones by Friedel-Crafts intramol. Michael addition in high yields. The reaction of di-Et 2-[(N-methyl-N-phenylcarbamoyl)methylene]malonate in the presence of ZnCl₂ gave I in excellent yield. The reactions also proceeded with a catalytic amount of a Lewis acid such as AlCl₃, ZnCl₂, ZnBr₂, Sc(OTf)₃, or InBr₃. In the experiment, the researchers used many compounds, for example, 3-(3,4-Dimethoxyphenyl)propan-1-ol (cas: 3929-47-3Name: 3-(3,4-Dimethoxyphenyl)propan-1-ol).

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

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

Synthesis of N-heteroarenemethyl esters via C-C bond cleavage of acyl cyanides under transition metal-free conditions was written by Lai, Miao;Su, Fangyao;Hu, Jingyi;Wang, Mengzhuo;Zhao, Mingqin;Zhang, Ganlin. And the article was included in Frontiers in Chemistry (Lausanne, Switzerland) in 2021.Safety of (6-Methoxypyridin-2-yl)methanol This article mentions the following:

A practical method to synthesize N-heteroaryl esters from N-heteroaryl methanols with acyl cyanides via C-C bond cleavage without using any transition metal is demonstrated here. The use of Na₂CO₃/15-crown-5 couple enables access to a series of N-heteroaryl esters in high efficiency. This protocol is operationally simple and highly environmentally benign producing only cyanides as byproducts. 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. 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).Safety of (6-Methoxypyridin-2-yl)methanol

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

Discovery of Novel, Potent Inhibitors of Hydroxy Acid Oxidase 1 (HAO1) Using DNA-Encoded Chemical Library Screening was written by Lee, Esther C. Y.;McRiner, Andrew J.;Georgiadis, Katy E.;Liu, Julie;Wang, Zooey;Ferguson, Andrew D.;Levin, Benjamin;von Rechenberg, Moritz;Hupp, Christopher D.;Monteiro, Michael I.;Keefe, Anthony D.;Olszewski, Allison;Eyermann, Charles J.;Centrella, Paolo;Liu, Yanbin;Arora, Shilpi;Cuozzo, John W.;Zhang, Ying;Clark, Matthew A.;Huguet, Christelle;Kohlmann, Anna. And the article was included in Journal of Medicinal Chemistry in 2021.Category: ethers-buliding-blocks This article mentions the following:

Inhibition of hydroxy acid oxidase 1 (HAO1) is a strategy to mitigate the accumulation of toxic oxalate that results from reduced activity of alanine-glyoxylate aminotransferase (AGXT) in primary hyperoxaluria 1 (PH1) patients. DNA-Encoded Chem. Library (DECL) screening provided two novel chem. series of potent HAO1 inhibitors, represented by compounds 3-6. Compound I was further optimized via various structure-activity relationship (SAR) exploration methods to II, a compound with improved potency and absorption, distribution, metabolism, and excretion (ADME)/pharmacokinetic (PK) properties. Since carboxylic acid-containing compounds are often poorly permeable and have potential active glucuronide metabolites, we undertook a brief, initial exploration of acid replacements with the aim of identifying non-acid-containing HAO1 inhibitors. Structure-based drug design initiated with Compound I led to the identification of a nonacid inhibitor of HAO1, III, which has weaker potency and increased permeability. In the experiment, the researchers used many compounds, for example, 3-Formyl-2-methoxyphenylboronic acid (cas: 480424-49-5Category: ethers-buliding-blocks).

3-Formyl-2-methoxyphenylboronic acid (cas: 480424-49-5) 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闂佺偨鍎茶ぐ濠囨煃閵夛箑鐤?linkages. In dimethyl ether, the bond angle is 111闁?and C闂佺偨鍎茶ぐ?distances are 141 pm. The barrier to rotation about the C闂佺偨鍎茶ぐ?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

Efficient Synthesis of Imines by Oxidative Coupling Catalyzed by Ce-Mn Oxide Microspheres was written by Chutimasakul, Threeraphat;Tirdtrakool, Warinda;Na Nakhonpanom, Pakamon;Kreethatorn, Hemmarat;Jaruwatee, Pattamaporn;Bunchuay, Thanthapatra;Tantirungrotechai, Jonggol. And the article was included in ChemistrySelect in 2022.Safety of (4-Methoxyphenyl)methanol This article mentions the following:

Oxidative self-coupling of amines and cross-coupling with alcs. are important reactions for the synthesis of imines; however, catalytic systems for these reactions usually require expensive oxidant, complicated catalyst preparation, complex reaction set-up, and/or additives such as bases or cocatalysts. Here, authors report that amorphous cerium-manganese (Ce-Mn) oxides with hierarchical microsphere structure prepared by a facile method could exhibit excellent catalytic performance for the synthesis of various imines using air as the green oxidant under mild conditions. The Ce-Mn oxide heterogeneous catalysts could also be easily recovered and efficiently recycled without significant loss of activities. The excellent activities and the reusability of the Ce-Mn oxide microspheres offer potential advances in the synthesis of imine. In the experiment, the researchers used many compounds, for example, (4-Methoxyphenyl)methanol (cas: 105-13-5Safety of (4-Methoxyphenyl)methanol).

(4-Methoxyphenyl)methanol (cas: 105-13-5) 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.Safety of (4-Methoxyphenyl)methanol

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

Rapid epoxy cure and transamination behavior in vinylogous urethane epoxy using glyme-metal ions was written by Shin, Jaeho;Yi, Mobeom;Kim, Hyunjoong. And the article was included in Koen Yoshishu – Nippon Setchaku Gakkai Nenji Taikai in 2021.Electric Literature of C8H18O4 This article mentions the following:

Here we fabricated three different types of ILs containing lithium or zinc ligand with glyme mol. The unique functions of ionic liquids to intervene oxirane and carbonyl oxygen made the metal-glyme mixture a potential latent cure accelerator in epoxy cure reaction and a catalyst of transamination reaction at the same time. In the experiment, the researchers used many compounds, for example, 2,5,8,11-Tetraoxadodecane (cas: 112-49-2Electric Literature of C8H18O4).

2,5,8,11-Tetraoxadodecane (cas: 112-49-2) 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).Electric Literature of C8H18O4

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

Copper(I)-catalyzed sulfonylative Suzuki-Miyaura cross-coupling was written by Chen, Yiding;Willis, Michael C.. And the article was included in Chemical Science in 2017.Category: ethers-buliding-blocks This article mentions the following:

By using a simple copper(I) catalyst a high yielding sulfonylative-Suzuki-Miyaura cross-coupling reaction was developed. The process provided a single step route to diaryl sulfones from the direct combination of arylboronic acids, sulfur dioxide and aryl iodides, and represents the first sulfonylative variant of a classic cross-coupling reaction. Sulfur dioxide was delivered from the surrogate reagent, DABSO. Variation of the reaction conditions allowed interruption of the sulfonylative-Suzuki coupling, resulted in the formation of a presumed Cu-sulfinate intermediate. These sulfinates was trapped as their sodium salts and treated with electrophiles to allow access to arylalkyl sulfones, 閻?hydroxyl sulfones, sulfonamides and sulfonyl fluorides. In the experiment, the researchers used many compounds, for example, (4-((4-Methoxybenzyl)oxy)phenyl)boronic acid (cas: 156635-90-4Category: ethers-buliding-blocks).

(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. 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.Category: ethers-buliding-blocks

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

Synthesis of monoazacrown ethers under phase-transfer catalysis was written by Luk’yanenko, N. G.;Basok, S. S.;Kulygina, E. Yu.;Bogashchenko, T. Yu.;Yakovenko, I. S.. And the article was included in Russian Journal of Organic Chemistry in 2012.Related Products of 66943-05-3 This article mentions the following:

A procedure was proposed for the synthesis of monoazacrown ethers by reaction of N-benzyldiethanolamine with oligo(ethylene glycol)-bis(p-toluene)sulfonates in a two-phase system aromatic hydrocarbon-50% aqueous alkali, followed by removal of the benzyl group by catalytic hydrogenolysis. The maximal yields of N-benzyl-aza-12-crown-4, -18-crown-6, and -21-crown-7 were achieved by adding 4-10 equiv of LiCl, BaBr₂, and CsCl, resp., to the reaction mixture, which probably indicated template effect. In the experiment, the researchers used many compounds, for example, 1,4,7,10-Tetraoxa-13-azacyclopentadecane (cas: 66943-05-3Related Products of 66943-05-3).

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, 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. 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.Related Products of 66943-05-3

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

Copper-Catalyzed Regioselective Olefination and Trifluoromethylation of Carboxylic Acids To Give (Z)-Trifluoromethyl Enol Esters was written by Lu, Dong;Li, Shuangshuang;Yang, Xiaogang;Yin, Shuang-Feng;Kambe, Nobuaki;Qiu, Renhua. And the article was included in Organic Letters in 2022.Electric Literature of C9H10O4 This article mentions the following:

A method to produce (Z)-trifluoromethyl enol esters via the olefination and trifluoromethylation of carboxylic acids with TMSCF₃ was reported. This synthetic method used inexpensive and easy-to-handle TMSCF₃. It employed a com. available CuCl catalyst to transform a broad range of carboxylic acids into versatile (Z)-trifluoromethyl enol esters with good regio- and stereoselectivity. This protocol allowed the concise synthesis of highly functionalized (Z)-trifluoromethyl enol esters directly from carboxylic acids. In the experiment, the researchers used many compounds, for example, 2-(4-Methoxyphenoxy)acetic acid (cas: 1877-75-4Electric Literature of C9H10O4).

2-(4-Methoxyphenoxy)acetic acid (cas: 1877-75-4) 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.Electric Literature of C9H10O4

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