Month: February 2023

Cobalt/Salox-Catalyzed Enantioselective C-H Functionalization of Arylphosphinamides was written by Yao, Qi-Jun;Chen, Jia-Hao;Song, Hong;Huang, Fan-Rui;Shi, Bing-Feng. And the article was included in Angewandte Chemie, International Edition in 2022.Application In Synthesis of 1,4-Dimethoxy-2-butyne This article mentions the following:

Previous methods on Co(III)-catalyzed asym. C-H activation rely on the use of tailor-made cyclopentadienyl-ligated Co(III) complexes, which require lengthy steps for the preparation Herein, the authors report an unprecedented enantioselective C-H functionalization enabled by a simple Co/salicyloxazoline (Salox) catalysis. The chiral Salox ligands can be easily prepared in one step from salicylonitrile and chiral amino alcs. A broad range of P-stereogenic compounds were synthesized in high yields with excellent enantioselectivities (45 examples, up to 99% yield and >99% ee). The isolation and characterization of several intermediates provided insights into the generation of active catalytic Co species, the action of Salox, and the mode of stereocontrol. In the experiment, the researchers used many compounds, for example, 1,4-Dimethoxy-2-butyne (cas: 16356-02-8Application In Synthesis of 1,4-Dimethoxy-2-butyne).

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. 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.Application In Synthesis of 1,4-Dimethoxy-2-butyne

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

Solvent effects on Li ion transference number and dynamic ion correlations in glyme- and sulfolane-based molten Li salt solvates was written by Shigenobu, Keisuke;Dokko, Kaoru;Watanabe, Masayoshi;Ueno, Kazuhide. And the article was included in Physical Chemistry Chemical Physics in 2020.Name: 2,5,8,11-Tetraoxadodecane This article mentions the following:

The Li⁺ transference number of electrolytes is one of the key factors contributing to the enhancement in the charge-discharge performance of Li secondary batteries. However, a design principle to achieve a high Li⁺ transference number has not been established for liquid electrolytes. To understand the factors governing the Li⁺ transference number t_Li, we investigated the influence of the ion-solvent interactions, Li ion coordination, and correlations of ion motions on the Li⁺ transference number in glyme (Gn, n = 1-4)- and sulfolane (SL)-based molten Li salt solvate electrolytes with lithium bis(trifluoromethansulfonyl)amide (LiTFSA). For the 1 : 1 tetraglyme-LiTFSA molten complex, [Li(G4)][TFSA], the Li⁺ transference number estimated using the potentiostatic polarisation method (t^PP_Li = 0.028) was considerably lower than that estimated using the self-diffusion coefficient data with pulsed filed gradient (PFG)-NMR (t^NMR_Li = 0.52). The dynamic ion correlations (i.e., cation-cation, anion-anion, and cation-anion cross-correlations) were determined from the exptl. data on the basis of Roling and Bedrov′s concentrated solution theory, and the results suggest that the strongly neg. cross-correlations of the ion motions (especially for cation-cation motions) are responsible for the extremely low t^PP_Li of [Li(G4)][TFSA]. In contrast, t^PP_Li is larger than t^NMR_Li in the SL-based electrolytes. The high t^PP_Li of the SL-based electrolytes was ascribed to the substantially weaker anti-correlations of cation-cation and cation-anion motions. Whereas the translational motions of the long-lived [Li(glyme)]⁺ and [TFSA]^– dominate the ionic conduction for [Li(G4)][TFSA], Li ion hopping/exchange conduction was reported to be prevalent in the SL-based electrolytes. The unique Li ion conduction mechanism is considered to contribute to the less correlated cation-cation and cation-anion motions in SL-based electrolytes. In the experiment, the researchers used many compounds, for example, 2,5,8,11-Tetraoxadodecane (cas: 112-49-2Name: 2,5,8,11-Tetraoxadodecane).

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.Name: 2,5,8,11-Tetraoxadodecane

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

Structure-based design of novel donepezil-like hybrids for a multi-target approach to the therapy of Alzheimer′s disease was written by Brunetti, Leonardo;Leuci, Rosalba;Carrieri, Antonio;Catto, Marco;Occhineri, Sara;Vinci, Giuseppe;Gambacorta, Lucia;Baltrukevich, Hanna;Chaves, Silvia;Laghezza, Antonio;Altomare, Cosimo Damiano;Tortorella, Paolo;Santos, M. Amelia;Loiodice, Fulvio;Piemontese, Luca. And the article was included in European Journal of Medicinal Chemistry in 2022.Name: 2-(4-Methoxyphenoxy)acetic acid This article mentions the following:

Alzheimer′s disease (AD) is a widespread multifactorial aging-related pathol., which includes cholinergic deficit among its main causes. Following a multi-target design strategy, the structure of the approved drug donepezil was taken as the starting point for generating some new potential multi-functional compounds Therefore, a series of twenty mol. hybrids were synthesized and assayed against three different enzymes, namely the well-established targets acetylcholinesterase (AChE) and butyrylcholinesterase (BChE), and the innovative one fatty acid amide hydrolase (FAAH). In silico studies confirmed the interaction of benzylpiperidine and the benzylpiperazine isostere with the catalytic anionic site (CAS) of AChE, while the aryloxycarbonyl portion appeared to be important for the interaction with the peripheral site (PAS). A QSAR study was carried out on AChE inhibition data, which revealed that the inhibition potency seems to depend upon the length of the spacer and the number of polar atoms. The docking poses of selected compounds within BChE and FAAH were also calculated Furthermore, pharmacokinetics and drug-likeness properties were assessed by chemoinformatic tools. Several piperidine derivatives (in particular compound 10) showed interesting profiles as multi-target directed agents, while the lead piperazine derivative 12 (SON38) was found to be a more potent and selective AChE inhibitor (IC50 = 0.8 nM) than donepezil, besides being able to bind bivalent copper cations (pCu = 7.9 at physiol. pH). Finally, the selected lead compounds (10 and 12, SON38) did not show significant cytotoxicity on SH-SY5Y and HepG2 cells at the highest tested concentration (100 μM) in a MTT assay. In the experiment, the researchers used many compounds, for example, 2-(4-Methoxyphenoxy)acetic acid (cas: 1877-75-4Name: 2-(4-Methoxyphenoxy)acetic acid).

2-(4-Methoxyphenoxy)acetic acid (cas: 1877-75-4) 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.Name: 2-(4-Methoxyphenoxy)acetic acid

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

Specific features of the reduction of disubstituted amide derivatives of p-tert-butylcalix[4]arene was written by Alekseeva, E. A.;Basok, S. S.;Rakipov, I. M.;Mazepa, A. V.;Gren’, A. I.. And the article was included in Russian Journal of Organic Chemistry in 2013.Formula: C10H21NO4 This article mentions the following:

Regardless of the reducing agent, the reduction at 25°C and at higher temperatures of the amide groups in a large number of p-tert-butylcalix[4]arene derivatives containing amide fragments with different substituents on the nitrogen atoms was accompanied by hydrogenolysis of the C-N bond with formation of the corresponding O-(2-hydroxyethyl)calixarenes and by partial cleavage of the ether bond between the calixarene framework and the substituent to give compounds with a lower degree of substitution. In the experiment, the researchers used many compounds, for example, 1,4,7,10-Tetraoxa-13-azacyclopentadecane (cas: 66943-05-3Formula: C10H21NO4).

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. 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.Formula: C10H21NO4

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

Rhodium(NHC)-Catalyzed O-Arylation of Aryl Bromides was written by Kim, Hyun Jin;Kim, Min;Chang, Sukbok. And the article was included in Organic Letters in 2011.Application of 54916-28-8 This article mentions the following:

The first example of the rhodium-catalyzed O-arylation of aryl bromides to give diarylethers, e.g., I, is reported. While the right combination of rhodium species and N-heterocyclic carbene (NHC) offered an effective catalytic system enabling the arylation to proceed, the choice of NHC was determined to be most important. The developed O-arylation protocol has a wide range of substrate scope, high functional group tolerance, and flexibility allowing a complementary route to either N- or O-arylation depending on the choice of NHC. In the experiment, the researchers used many compounds, for example, 1-(4-(4-Methoxyphenoxy)phenyl)ethanone (cas: 54916-28-8Application of 54916-28-8).

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

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

Kamlet-Taft solvatochromic parameters for 25 glycol ether solvents and glycol ether aqueous solutions was written by Lagalante, Anthony F.;Wood, Christian;Clarke, Adam M.;Bruno, Thomas J.. And the article was included in Journal of Solution Chemistry in 1998.Product Details of 20324-33-8 This article mentions the following:

The Kamlet-Taft parameters for 25 glycol ethers and their aqueous solutions were measured. Values for the three Kamlet-Taft parameters: the hydrogen-bond donor ability, hydrogen-bond acceptor ability, and the dipolarity/polarizability, as well as the index of refraction, were determined for each pure glycol either and each aqueous glycol solution A correlation matrix between other known solvent parameters and the measured Kamlet-Taft values revealed only one correlation, suggesting that the three measured Kamlet-Taft parameters for the glycol ethers are independent solvent descriptors. Last, trends in the measured Kamlet-Taft values were related to functional group modifications to the basic glycol ether structure. In the experiment, the researchers used many compounds, for example, 1-((1-((1-Methoxypropan-2-yl)oxy)propan-2-yl)oxy)propan-2-ol (cas: 20324-33-8Product Details of 20324-33-8).

1-((1-((1-Methoxypropan-2-yl)oxy)propan-2-yl)oxy)propan-2-ol (cas: 20324-33-8) 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. 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 20324-33-8

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

Iridium-Catalyzed Carbonylative Synthesis of Halogen-Containing Quinolin-2(1H)-ones from Internal Alkynes and Simple Anilines was written by Zhu, Fengxiang;Li, Yahui;Wang, Zechao;Wu, Xiao-Feng. And the article was included in Advanced Synthesis & Catalysis in 2016.COA of Formula: C6H10O2 This article mentions the following:

In this communication, a novel and efficient iridium-catalyzed carbonylative annulation of simple anilines with internal alkynes for the straightforward synthesis of halogen-containing quinolin-2(1H)-ones, e.g., I has been developed. The reaction proceeds without preactivation and directing groups through direct N-H and C-H bond activation with a broad substrate scope and high efficiency. Halogen functional groups can be well tolerated here. Remarkably, this is the first example of an iridium-catalyzed carbonylative C-H activation of anilines. In the experiment, the researchers used many compounds, for example, 1,4-Dimethoxy-2-butyne (cas: 16356-02-8COA of Formula: C6H10O2).

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. 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.COA of Formula: C6H10O2

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

Catalytic amination in the synthesis of hybrid polymacrocycles comprising porphyrin and azacrown ether moieties was written by Yakushev, Alexei A.;Averin, Alexei D.;Maloshitskaya, Olga A.;Syrbu, Sergei A.;Koifman, Oskar I.;Beletskaya, Irina P.. And the article was included in Mendeleev Communications in 2016.Quality Control of 1,4,7,10-Tetraoxa-13-azacyclopentadecane This article mentions the following:

Pd⁰-catalyzed amination of 3-bromobenzyl-substituted azacrown ethers with propane-1,3-diamine affords the 3-(3-aminopropyl)benzyl derivatives, whose reaction with meso-(bromophenyl)-substituted porphyrins leads to bis- and trismacrocyclic conjugates. 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

Optimization of catalytic reaction for synthesis of 2-methyl-4-methoxydiphenylamine was written by Cho, Jeong-Woo;Kim, Eun-Seok;Kim, Kiseok;Kim, Seong-Hoon. And the article was included in Kongop Hwahak in 1999.Safety of 3-Methyl-4-nitroanisole This article mentions the following:

Reaction mechanism was elucidated and reaction condition were optimized for the catalytic reaction synthesizing 2-methyl-4-methoxydiphenylamine (MMDPA) which is an intermediate of Fluoran heat-sensitive dyestuff. Reactants consisted of 2-methyl-4-methoxyaniline (MMA), 3-methyl-4-nitroanisole (MNA), and cyclohexanone, and 5 wt% Pd/C was used as a catalyst. Experiments were run in an open slurry reactor equipped with reflux condenser, and products were analyzed by means of GC/MS and NMR. MMDPA yield of 90 mol % could be obtained after reaction time of 8�0 h under the optimal reaction conditions comprising the reaction mass composition of MMA:MNA:cyclohexanone = 1:2:150 based on MMA input of 0.01 gmoles in xylene solvent, reaction temperature of 160°C, and catalyst amount of 0.5 g. It was found that the rate-determining step of overall reaction was dehydrogenation of the intermediate product obtained from condensation of MMA and cyclohexanone. Overall reaction rate and MMDPA yield were enhanced owing to hydrogen transfer reaction by introducing MNA together with MMA in the reaction mass. Excess cyclohexanone in the reaction mass played an important role of promoting the condensation of MMA and cyclohexanone. In the experiment, the researchers used many compounds, for example, 3-Methyl-4-nitroanisole (cas: 5367-32-8Safety of 3-Methyl-4-nitroanisole).

3-Methyl-4-nitroanisole (cas: 5367-32-8) 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. 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 3-Methyl-4-nitroanisole

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