Month: February 2023

Synthesis of quinolines via ortho-lithiated N-acylanilines. A modified Friedlaender synthesis was written by Cho, In Seop;Gong, Leyi;Muchowski, Joseph M.. And the article was included in Journal of Organic Chemistry in 1991.Electric Literature of C12H17NO2 This article mentions the following:

A new variation of the Friedlaender quinoline synthesis was devised based on the sequential reaction of ortho-lithiated N–tert-Boc-anilines or N-pivaloylanilines with masked malondialdehyde derivatives, e.g., vinamidinium salts I (R = H, Ph), 3-(dimethylamino)acrolein, and 3-ethoxymethacrolein, and subsequent acid-induced cyclization. Thus, anilines II (R¹ = H, F, Cl, Me, OMe, R² = OCMe₃) were lithiated and cyclized with I (R = H) to give quinolines III. Lithiation of II (R¹ = F, R² = CMe₃) and cyclization with EtOCH:CMeCHO gave III (R¹ = F, R = Me). In the experiment, the researchers used many compounds, for example, N-(3-Methoxyphenyl)pivalamide (cas: 56619-93-3Electric Literature of C12H17NO2).

N-(3-Methoxyphenyl)pivalamide (cas: 56619-93-3) 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. 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.Electric Literature of C12H17NO2

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

Electrochemical Synthesis of Aryl Methoxymethyl Ethers was written by de Kruijff, Goswinus H. M.;Waldvogel, Siegfried R.. And the article was included in ChemElectroChem in 2019.Product Details of 1877-75-4 This article mentions the following:

Methoxymethyl protected phenols/thiophenols ArXCH₂OCH₃ [X = O, S; Ar = Ph, 4-ClC₆H₄, 2,6-di-ClC₆H₃, etc.] were synthesized by safe, reagent- and reagent waste-free anodic decarboxylation protocol. High current efficiencies and good functional group tolerance made this methodol. a useful tool for the preparation of these valuable and protected phenol building blocks. In the experiment, the researchers used many compounds, for example, 2-(4-Methoxyphenoxy)acetic acid (cas: 1877-75-4Product Details of 1877-75-4).

2-(4-Methoxyphenoxy)acetic acid (cas: 1877-75-4) 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. 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).Product Details of 1877-75-4

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

Enantioselective Synthesis of Planar-Chiral Macrocycles through Asymmetric Electrophilic Aromatic Amination was written by Wang, Donglei;Shao, Ying-Bo;Chen, Yunrong;Xue, Xiao-Song;Yang, Xiaoyu. And the article was included in Angewandte Chemie, International Edition in 2022.Product Details of 105-13-5 This article mentions the following:

An efficient approach for asym. synthesis of planar-chiral macrocycles (paracyclophanes) has been disclosed through enantioselective electrophilic aromatic aminations with azodicarboxylates enabled by chiral phosphoric acid catalysis. A wide range of chiral macrocycles bearing varied ring sizes (16 to 23-membered) and functional group-containing ansa chains were readily afforded using this method, with excellent yields and high enantioselectivities (23 examples, up to 99.5 : 0.5 er). Exptl. studies and DFT calculations were performed to elucidate the mechanism and origin of stereoselectivities of these reactions. Preliminary utilization of the planar-chiral macrocycle as chiral organocatalyst showcased the potential applications of these novel chiral skeletons. In the experiment, the researchers used many compounds, for example, (4-Methoxyphenyl)methanol (cas: 105-13-5Product Details of 105-13-5).

(4-Methoxyphenyl)methanol (cas: 105-13-5) 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 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 105-13-5

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

Interception of Nickel Hydride Species and Its Application in Multicomponent Reactions was written by Balakrishnan, Venkadesh;Ganguly, Anirban;Rasappan, Ramesh. And the article was included in Organic Letters in 2022.Category: ethers-buliding-blocks This article mentions the following:

The hydrogen borrowing strategy is an economical method for the 浼?functionalization of ketones. While this strategy is extremely advantageous, it does not lend itself to the synthesis of 灏?灏?disubstituted ketones. This can be achieved, if the in situ generated metal hydride can be intercepted with a nucleophilic coupling partner. Authors present a multicomponent strategy for the coupling of alcs., ketones, and boronic acids using only 1 mol % nickel catalyst and without the need for added ligands. In the experiment, the researchers used many compounds, for example, (4-Methoxyphenyl)methanol (cas: 105-13-5Category: ethers-buliding-blocks).

(4-Methoxyphenyl)methanol (cas: 105-13-5) 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. Ethers can form hydrogen bonds with other molecules (alcohols, amines, etc.) that have O閳ユ椊 or N閳ユ椊 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

Study on the removal and depolymerization of lignin from corn stover through the synergistic effect of Bronsted acid, Lewis acid and hydrogenation sites was written by Zhang, Baikai;Li, Wenzhi;Zhang, Tingwei;Li, Xu;Ogunbiyi, Ajibola T.;Chen, Kun;Shen, Changcheng. And the article was included in Fuel in 2021.Electric Literature of C11H16O3 This article mentions the following:

The effective transformation of lignin is an essential part of realizing the comprehensive utilization of biomass. In this study, a one-pot method for the depolymerization of corn stover lignin used aluminum phosphate (NiAPO-5) zeolite catalyst contained Bronsted acid, Lewis acid and hydrogenation sites was proposed. It was found that the number of Bronsted acid sites was increased after NiAPO-5 was reduced with H₂. The yield of monomers and residue were 35.70% and 38.09% at 235鎺矯 for 3 h, resp. The result of 2D HSQC NMR showed that the NiAPO-5 (H₂) catalyst significantly affected the cleavage of 灏?O-4 bonds. The distribution of products and the stability of catalyst revealed that NiAPO-5 (H₂) was an efficient catalyst for the depolymerization of lignin. 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. 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).Electric Literature of C11H16O3

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

Modification of gold surface by electrosynthesized mono aza crown ether substituted catechol-terminated alkane dithiol and its application as a new electrochemical sensor for trace detection of cadmium ions was written by Dehdashtian, Sara;Shamsipur, Mojtaba. And the article was included in Colloids and Surfaces, B: Biointerfaces in 2018.Quality Control of 1,4,7,10-Tetraoxa-13-azacyclopentadecane This article mentions the following:

Among the toxic metals, cadmium is a very dangerous pollutant because it can extremely damage organs in humans and animals. This toxic metal is introduced into water from different industries such as metal plating, batteries, and alloys. Cadmium bioaccumulates in vital organs and unlike organic pollutants does not show any biol. degradation In this study, an electroactive self-assembled monolayer (SAM) was developed by covalent attachment of a novel mono aza-crown ether substituted catechol-terminated hexane dithiol onto the gold surface. The electrochem. behavior of the fabricated SAM electrode was investigated using voltammetry techniques and electrochem. impedance spectroscopy (EIS). The obtained results from voltammetric experiments revealed that the crown ether moiety of SAM forms a selective complex with cadmium ion. Under optimal conditions, Cd²⁺ could be detected in the range of 15娓璏 to 65娓璏 with a detection limit of 4.5娓璏. Selectivity measurements reveal that the sensor is specific for Cd²⁺ even in the presence of high concentrations of other metal ions. The proposed sensor was applied to the determination of cadmium ion in water samples with high sensitivity and good selectivity. In the experiment, the researchers used many compounds, for example, 1,4,7,10-Tetraoxa-13-azacyclopentadecane (cas: 66943-05-3Quality Control of 1,4,7,10-Tetraoxa-13-azacyclopentadecane).

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).Quality Control of 1,4,7,10-Tetraoxa-13-azacyclopentadecane

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

Carbolines. Part VII. Anisidines, convenient tools to synthesize hydroxy-灏?carbolines was written by Rocca, Patrick;Marsais, Francis;Godard, Alain;Queguiner, Guy;Adams, Luqman;Alo, Babajide. And the article was included in Journal of Heterocyclic Chemistry in 1995.HPLC of Formula: 56619-93-3 This article mentions the following:

The paper describes a convenient synthesis of hydroxy-灏?carbolines from com. anisidines based on key steps such as metalation, cross-coupling and cyclization. The first total synthesis of a major cytotoxic constituent of a marine bryozoan is also reported, the 8-hydroxy-1-vinyl-灏?carboline. In the experiment, the researchers used many compounds, for example, N-(3-Methoxyphenyl)pivalamide (cas: 56619-93-3HPLC of Formula: 56619-93-3).

N-(3-Methoxyphenyl)pivalamide (cas: 56619-93-3) 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. 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: 56619-93-3

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

A novel multikinase inhibitor SKLB-YTH-60 ameliorates inflammation and fibrosis in bleomycin-induced lung fibrosis mouse models was written by Liu, Hongyao;Wu, Xiuli;Gan, Cailing;Wang, Liqun;Wang, Guan;Yue, Lin;Liu, Zhihao;Wei, Wei;Su, Xingping;Zhang, Qianyu;Tan, Zui;Yao, Yuqin;Ouyang, Liang;Yu, Luoting;Ye, Tinghong. And the article was included in Cell Proliferation in 2021.Synthetic Route of C14H21BO4 This article mentions the following:

Idiopathic pulmonary fibrosis (IPF) is marked by the excessive accumulation of extracellular matrix, which participates in a variety of chronic diseases or injuries and seriously threatens human health. Due to the side effects of clin. drugs, there is still a need to develop novel and less toxic drugs to treat pulmonary fibrosis. SKLB-YTH-60 was developed through computer-aided drug design, de novo synthesis and high-throughput screening. We employed the bleomycin (BLM)-induced lung fibrosis animal models and used TGF-灏?sub>1 to induce the epithelial-mesenchymal transition (EMT) of A549 cells in vitro. Meanwhile, the protein expression of collagen I and the 浼?smooth muscle actin (浼?SMA), E-cadherin, p-FGFR1, p-PLC绾? p-Smad2/3 and p-Erk1/2 was detected by western blot. YTH-60 has obvious anti-proliferative activity on fibroblasts and A549 cells. Moreover, YTH-60 could impair the EMT of A549 cells and suppressed fibrosis by inhibiting FGFR and TGF-灏?Smad-dependent pathways. I.p. administration of preventive YTH-60 could significantly reduce the degree of fibrosis in mice and regulate the imbalance of the immune microenvironment. In addition, we observed that therapeutic YTH-60 treatment attenuated fibrotic changes in mice during the period of fibrosis. Importantly, YTH-60 has shown an acceptable oral bioavailability (F = 17.86%) and appropriate eliminated half-life time (T_1/2 = 8.03 h). Taken together, these preclin. evaluations suggested that YTH-60 could be a promising drug candidate for treating IPF. 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. 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 C14H21BO4

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

Efficacy of stabilizing calcium battery electrolytes through salt-directed coordination change was written by Hahn, Nathan T.;McClary, Scott A.;Landers, Alan T.;Zavadil, Kevin R.. And the article was included in Journal of Physical Chemistry C in 2022.SDS of cas: 112-49-2 This article mentions the following:

Achieving practical, high-energy-d. calcium batteries requires controlling the stability of Ca²⁺ electrolytes during calcium metal cycling. Because of the highly reactive nature of calcium, most typical electrolyte constituents are unstable, leading to electrode passivation and low Coulombic efficiency. Among various com. available salts, calcium bis(trifluoromethylsulfonyl)imide (Ca(TFSI)₂) is attractive because of its oxidative stability and high solubility in a variety of solvents. However, this salt does not allow for calcium metal plating, and it has been proposed that TFSI^– instability induced by Ca²⁺ coordination is to blame. In this work, we test the ability of strongly coordinating Ca²⁺ cosalts such as halides and borohydrides to displace TFSI^– from the first coordination shell of Ca²⁺ and thereby stabilize TFSI-based electrolytes to enable calcium plating. Through spectroscopic anal., we find that the effectiveness of these cosalts at displacing the TFSI^– anion is dependent on the solvent’s coordination strength toward Ca²⁺. Surprisingly, electrochem. calcium deposition behavior is not correlated to the population of bound or free TFSI^–. Instead, the nature of the coordination interaction between Ca²⁺ and the cosalt anion is more important for determining stability. Our findings indicate that TFSI^– anions are inherently unstable during calcium deposition even in the nominally free state. Therefore, strategies aimed at eliminating the interactions of these anions with the electrode surface via interface/interphase design are required. In the experiment, the researchers used many compounds, for example, 2,5,8,11-Tetraoxadodecane (cas: 112-49-2SDS of cas: 112-49-2).

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

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

Discovery of an Oral, Rule of 5 Compliant, Interleukin 17A Protein-Protein Interaction Modulator for the Potential Treatment of Psoriasis and Other Inflammatory Diseases was written by Andrews, Mark D.;Dack, Kevin N.;de Groot, Marcel J.;Lambert, Maja;Sennbro, Carl J.;Larsen, Mogens;Stahlhut, Martin. And the article was included in Journal of Medicinal Chemistry in 2022.COA of Formula: C8H10O2 This article mentions the following:

Interleukin 17A (IL-17A) was an interleukin cytokine whose dysregulation implicated in autoimmune disorders such as psoriasis and monoclonal antibodies against the IL-17A pathway were now well-established and very effective treatments. Overlap of early ligands led to a series of benzhydrylglycine-containing compounds I [R¹ = C(O)N(Me)₂, pyrazol-4-yl, 3,5-(Me)₂-pyrazol-4-yl, etc.; R² = cyclopropyl, cyclohexyl, Ph, etc.; R³ = H, cyclopropyl Ph, etc.; R²R³ = Ph, cyclohexyl, cycloheptyl, etc.; R⁴ = Me, Et, iPr] that allowed foridentifying dimethylpyrazole as a key substituent that gave moderately potent PPIm with good oral bioavailability. Finally, optimization of the terminal amide group led to the identification of PPIm I [R¹ = 3,5-(Me)₂-pyrazol-4-yl; R² = cyclopropyl; R³ = cyclopropyl; R⁴ = iPr] as a clin. development candidate with the potential to be an oral treatment of IL-17A-mediated diseases. Protein crystallog. provided knowledge of the key binding interactions between small-mol. ligands and the IL-17A dimer and this helped in the multiparameter optimization toward identifying an orally bioavailable, Rule of 5 compliant PPIm of IL-17A. Exploration of the amino acid portion of the structure then led to dicyclopropylalanine as a group that gave potent and metabolically stable compounds, including the development candidate I [R¹ = 3,5-(Me)₂-pyrazol-4-yl; R² = cyclopropyl; R³ = cyclopropyl; R⁴ = iPr]. In the experiment, the researchers used many compounds, for example, (4-Methoxyphenyl)methanol (cas: 105-13-5COA of Formula: C8H10O2).

(4-Methoxyphenyl)methanol (cas: 105-13-5) 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. 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.COA of Formula: C8H10O2

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