Category: ethers-buliding-blocks

Complementary site-selectivity in arene functionalization enabled by overcoming the ortho constraint in palladium/norbornene catalysis was written by Wang, Jianchun;Li, Renhe;Dong, Zhe;Liu, Peng;Dong, Guangbin. And the article was included in Nature Chemistry in 2018.Name: 4-Iodo-1-methoxy-2-methylbenzene This article mentions the following:

Achieving site-selectivity in arene functionalization that is complementary to the site-selectivity from electrophilic aromatic substitution reactions has been a long-standing quest in organic synthesis. Palladium/norbornene cooperative catalysis potentially offers a unique approach to this problem, but its use has been hampered by the ortho constraint, which is the requirement of an ortho substituent for mono ortho functionalization of haloarenes. Here, we show that such a challenge could be addressed using a new class of bridgehead-modified norbornenes, thereby enabling a broadly useful strategy for arene functionalization with complementary site-selectivity. A range of ortho-unsubstituted aryl iodides, previously problematic substrates, can now be employed to provide mono ortho-functionalized products effectively. This method is applicable for late-stage functionalization of complex bioactive mols. at positions that are difficult to reach by conventional approaches. In the experiment, the researchers used many compounds, for example, 4-Iodo-1-methoxy-2-methylbenzene (cas: 75581-11-2Name: 4-Iodo-1-methoxy-2-methylbenzene).

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

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

An ion-responsive fluorescent compound based on NO-photoisomerisation styryl derivative linked to monoaza-15-crown-5 was written by Cao, Jing;Feng, Jun Xiang;Wu, Yong Xiang;Pei, Xue Qun;Yan, Jiao Jiao;Liu, Yang;Qin, Wen Jie;Zhang, Xiao Bin. And the article was included in Supramolecular Chemistry in 2011.Computed Properties of C10H21NO4 This article mentions the following:

A novel 15-aza-5-crown ether linked to styryl chemosensory 13-(4-((9H-fluoren-9-ylidene)methyl)-2-nitrophenyl)-1,4,7,10-tetraoxa-13-azacyclopentadecane was designed and synthesized, it would not occur during photoisomerization under radiation of light but shows special capability of selectively recognizing for Sr²⁺. In the experiment, the researchers used many compounds, for example, 1,4,7,10-Tetraoxa-13-azacyclopentadecane (cas: 66943-05-3Computed Properties of C10H21NO4).

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. 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).Computed Properties of C10H21NO4

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

Evaluation of acrylophenones and related bis-Mannich bases against murine P388 leukemia was written by Dimmock, Jonathan R.;Patil, Shirish A.;Leek, Donald M.;Warrington, Robert C.;Fang, Wei D.. And the article was included in European Journal of Medicinal Chemistry in 1987.HPLC of Formula: 54916-28-8 This article mentions the following:

Mannich reaction of acetophenones with bases gave acrylophenones and bis-Mannich bases I and II (R = H, Me, Cl, OMe; R¹ = H, Cl; R² = H, OMe, Me, OPh, OC₆H₄OMe-4, OC₆H₄Me-4, OC₆H₄Cl-4; R³ = H, OMe, Me). I and II were tested against P388 lymphocyte leukemia in mice. I (R = R¹ = R³ = H, R² = OMe) shows potent activity against P388 cells in vitro. In the experiment, the researchers used many compounds, for example, 1-(4-(4-Methoxyphenoxy)phenyl)ethanone (cas: 54916-28-8HPLC of Formula: 54916-28-8).

1-(4-(4-Methoxyphenoxy)phenyl)ethanone (cas: 54916-28-8) 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).HPLC of Formula: 54916-28-8

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

Nickel-Catalyzed Reaction of Thioisatins and Alkynes: A Facile Synthesis of Thiochromones was written by Inami, Tasuku;Kurahashi, Takuya;Matsubara, Seijiro. And the article was included in Organic Letters in 2014.Safety of 1,4-Dimethoxy-2-butyne This article mentions the following:

A new synthetic method for thiochromones was developed by using nickel-catalyzed decarbonylative cycloaddition of readily available thioisatins with alkynes. This reaction proceeded under very mild conditions and has quite high functional group compatibility. In the experiment, the researchers used many compounds, for example, 1,4-Dimethoxy-2-butyne (cas: 16356-02-8Safety of 1,4-Dimethoxy-2-butyne).

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. 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-Dimethoxy-2-butyne

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

Directed Evolution of a Cp*Rh^III-Linked Biohybrid Catalyst Based on a Screening Platform with Affinity Purification was written by Kato, Shunsuke;Onoda, Akira;Taniguchi, Naomasa;Schwaneberg, Ulrich;Hayashi, Takashi. And the article was included in ChemBioChem in 2021.Safety of 1,4-Dimethoxy-2-butyne This article mentions the following:

Directed evolution of Cp*Rh^III-linked nitrobindin (NB), a biohybrid catalyst, was performed based on an in vitro screening approach. A key aspect of this effort was the establishment of a high-throughput screening (HTS) platform that involves an affinity purification step employing a starch-agarose resin for a maltose binding protein (MBP) tag. The HTS platform enables efficient preparation of the purified MBP-tagged biohybrid catalysts in a 96-well format and eliminates background influence of the host E. coli cells. Three rounds of directed evolution and screening of more than 4000 clones yielded a Cp*Rh^III-linked NB(T98H/L100K/K127E) variant with a 4.9-fold enhanced activity for the cycloaddition of acetophenone oximes with alkynes. It is confirmed that this HTS platform for directed evolution provides an efficient strategy for generating highly active biohybrid catalysts incorporating a synthetic metal cofactor. In the experiment, the researchers used many compounds, for example, 1,4-Dimethoxy-2-butyne (cas: 16356-02-8Safety of 1,4-Dimethoxy-2-butyne).

1,4-Dimethoxy-2-butyne (cas: 16356-02-8) 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. 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 1,4-Dimethoxy-2-butyne

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

Room-Temperature Direct Arylation of Anilides under External Oxidant-Free Conditions Using CO₂-Derived Dimethyl Carbonate (DMC) as a ‘Green’ Solvent was written by Sahoo, Manoj K.;Rana, Jagannath;Subaramanian, Murugan;Balaraman, Ekambaram. And the article was included in ChemistrySelect in 2017.Reference of 56619-93-3 This article mentions the following:

Here, an efficient catalytic protocol for direct C-H bond arylation of anilides under base- and external oxidant-free conditions is reported. This reaction proceeds readily at room temperature using CO₂-derived di-Me carbonate (DMC) as a ‘green’ solvent under visible-light dual catalysis. Later, application of this strategy for the gram-scale synthesis of Boscalid has been successfully shown. An unprecedented unsym. bis-arylation of anilides is also demonstrated under mild, redox-neutral conditions. In the experiment, the researchers used many compounds, for example, N-(3-Methoxyphenyl)pivalamide (cas: 56619-93-3Reference of 56619-93-3).

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.Reference of 56619-93-3

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

Intercalation/De-Intercalation Reactions of Lithium Ion at Graphite in Electrolyte Solutions Containing 3D-Transition-Metal Ions and Cyclic Ethers was written by Domi, Yasuhiro;Doi, Takayuki;Ochida, Manabu;Yamanaka, Toshiro;Abe, Takeshi;Ogumi, Zempachi. And the article was included in Journal of the Electrochemical Society in 2016.Name: 1,4,7,10-Tetraoxa-13-azacyclopentadecane This article mentions the following:

The effects of 3d-transition-metal ions in the electrolyte on the intercalation/de-intercalation reactions of Li⁺ at graphite neg.-electrodes were investigated. The edge plane of highly oriented pyrolytic graphite (HOPG) was used as a model electrode, and electrochem. properties were investigated by cyclic voltammetry and electrochem. impedance spectroscopy. A drastic decrease in redox current due to intercalation/de-intercalation reactions of Li⁺ was observed in electrolyte solutions containing Fe, Co, Ni, and Mn ions. In addition, interfacial resistance between the edge plane HOPG electrode and the electrolyte increased significantly. The effects of cyclic ethers, such as crown ether, aza crown ether, and cryptand, as electrolyte additives were applied to suppress the degradation of graphite neg.-electrodes. As a result, specific cyclic ethers greatly suppressed the degradation of edge plane HOPG neg.-electrodes in electrolyte solutions containing the above transition-metal ions. 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. 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 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.Name: 1,4,7,10-Tetraoxa-13-azacyclopentadecane

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

Structure-Functional Selectivity Relationship Studies on A-86929 Analogs and Small Aryl Fragments toward the Discovery of Biased Dopamine D1 Receptor Agonists was written by Li, Haoxi;Mirabel, Rosa;Zimmerman, Joseph;Ghiviriga, Ion;Phidd, Darian K.;Horenstein, Nicole;Urs, Nikhil M.. And the article was included in ACS Chemical Neuroscience in 2022.Recommanded Product: 3929-47-3 This article mentions the following:

Dopamine regulates normal functions such as movement, reinforcement learning, and cognition, and its dysfunction has been implicated in multiple psychiatric and neurol. disorders. Dopamine acts through D1- (D1R and D5R) and D2-class (D2R, D3R, and D4R) receptors and activates both G protein- and 閻?arrestin-dependent signaling pathways. Current dopamine receptor-based therapies are used to ameliorate motor deficits in Parkinson’s disease or as antipsychotic medications for schizophrenia. These drugs show efficacy for ameliorating only some symptoms caused by dopamine dysfunction and are plagued by debilitating side effects. Studies in primates and rodents have shown that shifting the balance of dopamine receptor signaling toward the arrestin pathway can be beneficial for inducing normal movement, while reducing motor side effects such as dyskinesias, and can be efficacious at enhancing cognitive function compared to balanced agonists. Several structure-activity relationship (SAR) studies have embarked on discovering 閻?arrestin-biased dopamine agonists, focused on D2 partial agonists, noncatechol D1 agonists, and mixed D1/D2R dopamine receptor agonists. Here, we describe an SAR study to identify novel D1R 閻?arrestin-biased ligands using A-86929, a high-affinity D1R catechol agonist, as a core scaffold to identify chem. motifs responsible for 閻?arrestin-biased activity at both D1 and D2Rs. Most of the A-86929 analogs screened were G protein-biased, but none of them were exclusively arrestin-biased. Addnl., various small-fragment mol. probes displayed weak bias toward the 閻?arrestin pathway. Continued in-depth SFSR (structure-functional selectivity relationship) studies informed by structure determination, mol. modeling, and mutagenesis studies will facilitate the discovery of potent and efficacious arrestin-biased dopamine receptor ligands. In the experiment, the researchers used many compounds, for example, 3-(3,4-Dimethoxyphenyl)propan-1-ol (cas: 3929-47-3Recommanded Product: 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. 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).Recommanded Product: 3929-47-3

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

Allylations of aryl/heteroaryl ketones: neat, clean and sustainable. Applications to targets in the pharma- and nutraceutical industries was written by Li, Xiaohan;Wood, Alex B.;Lee, Nicholas R.;Gallou, Fabrice;Lipshutz, Bruce H.. And the article was included in Green Chemistry in 2022.Quality Control of 2,3-Dimethoxy-5-methylcyclohexa-2,5-diene-1,4-dione This article mentions the following:

Aromatic and heteroaromatic ketones bearing an 濞?methine proton could be deprotonated and mono-allylated in minutes in the complete absence of an organic solvent to arrive at the corresponding allylated ketone products in high isolated yields. Applications to synthetic targets including both compounds I [n = 6, 8], as well as coenzyme II, utilizing this new technol. were documented. In the experiment, the researchers used many compounds, for example, 2,3-Dimethoxy-5-methylcyclohexa-2,5-diene-1,4-dione (cas: 605-94-7Quality Control of 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. 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.Quality Control of 2,3-Dimethoxy-5-methylcyclohexa-2,5-diene-1,4-dione

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

Cobalt-catalyzed cyclization of N-methoxy benzamides with alkynes using an internal oxidant through C-H/N-O bond activation was written by Sivakumar, Ganesan;Vijeta, Arjun;Jeganmohan, Masilamani. And the article was included in Chemistry – A European Journal in 2016.Reference of 16356-02-8 This article mentions the following:

The cyclization of substituted N-methoxy benzamides with alkynes in the presence of an easily affordable cobalt complex and NaOAc provided isoquinolone derivatives, e.g., I in good to excellent yields. The cyclization reaction was compatible with a range of functional group-substituted benzamides, as well as ester- and alc.-substituted alkynes. The cobalt complex [Co^IIICp*(OR)₂] (R = Me or Ac) served as an efficient catalyst for the cyclization reaction. Later, isoquinolone derivatives were converted into 1-chloro and 1-bromo substituted isoquinoline derivatives in excellent yields in the presence of POCl₃ or PBr₃. In the experiment, the researchers used many compounds, for example, 1,4-Dimethoxy-2-butyne (cas: 16356-02-8Reference of 16356-02-8).

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. 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.Reference of 16356-02-8

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