Author: Jessica.F

A formal intermolecular [4+2] cycloaddition reaction of 1,3-disubstituted indoles and alkylquinones was written by Lin, Chao;Du, Hong-Jin;Zhao, Hui;Yan, Ding-Fei;Liu, Nai-Xin;Sun, Hongbin;Wen, Xiaoan;Xu, Qing-Long. And the article was included in Organic & Biomolecular Chemistry in 2017.Application In Synthesis of 2,3-Dimethoxy-5-methylcyclohexa-2,5-diene-1,4-dione This article mentions the following:

A formal [4+2] cycloaddition reaction of 1,3-disubstituted indoles and alkylquinones was realized to furnish polycyclic indolines in good yields. This protocol proceeded smoothly under basic conditions, with high atom-economy and broad substrate scope. In the experiment, the researchers used many compounds, for example, 2,3-Dimethoxy-5-methylcyclohexa-2,5-diene-1,4-dione (cas: 605-94-7Application In Synthesis 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. 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).Application In Synthesis of 2,3-Dimethoxy-5-methylcyclohexa-2,5-diene-1,4-dione

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

Melting synthesis of 2-[(aryloxy)methyl]benzimidazole derivatives was written by Li, Yingjun;Liu, Lijun;Jin, Kun;Wang, Wei;Zhao, Nan;Li, Lina;Li, Chunyan. And the article was included in Youji Huaxue in 2009.Safety of 2-(4-Methoxyphenoxy)acetic acid This article mentions the following:

Several 2-[(aryloxy)methyl]benzimidazole derivatives were obtained by a reaction of benzenediamine with aryloxyacetic acid derivatives using a melting method. The products were confirmed by IR and NMR techniques. In this method, the molar ratio of o-phenylenediamine and aryloxyacetic acid is 1:1.1, and the reaction temperature is 180°. The above-mentioned method has the advantages of simple operation, short reaction time, easy purification, few byproducts, moderate to high yields and green synthesis. In the experiment, the researchers used many compounds, for example, 2-(4-Methoxyphenoxy)acetic acid (cas: 1877-75-4Safety of 2-(4-Methoxyphenoxy)acetic acid).

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

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

Switch-on diketopyrrolopyrrole-based chemosensors for cations possessing Lewis acid character was written by Kumar, G. Dinesh;Banasiewicz, Marzena;Jacquemin, Denis;Gryko, Daniel T.. And the article was included in Chemistry – An Asian Journal in 2021.Application In Synthesis of 1,4,7,10-Tetraoxa-13-azacyclopentadecane This article mentions the following:

For the first time diketopyrrolopyrroles (DPPs) have been synthesized directly from nitriles possessing (aza)crown ethers leading to macrocycle-dye hybrids. Depending on the nature of the linkage between DPP and macrocyclic ring, various coordination effects are found. The strong interaction of the cations possessing Lewis acid character such as Li⁺, Mg²⁺ and Zn²⁺ with 2-aminopyridin-4-yl-DPPs, leading to a bathochromic shift of both emission and absorption, as well as to strong enhancement of fluorescence was rationalized in terms of strong binding of these cations to the N=C-NR₂ functionality. The same effect has been observed for protonation. Depending on the size and the structure of the macrocyclic ring the complexation of cations by aza-crown ethers plays an important but secondary role. The interaction of Na⁺ and K⁺ with 2-aminopyridin-4-yl-DPPs leads to moderate enhancement of fluorescence due to the aza-crown ethers binding. The very weak fluorescence of DPP bearing 2-dialkylamino-pyridine-4-yl substituents is due to the closely lying T₂ state and the resulting intersystem crossing. In the experiment, the researchers used many compounds, for example, 1,4,7,10-Tetraoxa-13-azacyclopentadecane (cas: 66943-05-3Application In Synthesis of 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. 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.Application In Synthesis of 1,4,7,10-Tetraoxa-13-azacyclopentadecane

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

A New Approach To Predict the Biological Activity of Molecules Based on Similarity of Their Interaction Fields and the logP and logD Values: Application to Auxins was written by Bertosa, Branimir;Kojic-Prodic, Biserka;Wade, Rebecca C.;Ramek, Michael;Piperaki, Stavroula;Tsantili-Kakoulidou, Anna;Tomic, Sanja. And the article was included in Journal of Chemical Information and Computer Sciences in 2003.HPLC of Formula: 1877-75-4 This article mentions the following:

The activity of a biol. compound is dependent both on specific binding to a target receptor and its ADME (Absorption, Distribution, Metabolism, Excretion) properties. A challenge to predict biol. activity is to consider both contributions simultaneously in deriving quant. models. We present a novel approach to derive QSAR models combining similarity anal. of mol. interaction fields (MIFs) with prediction of logP and/or logD. This new classification method is applied to a set of about 100 compounds related to the auxin plant hormone. The classification based on similarity of their interaction fields is more successful for the indole than the phenoxy compounds The classification of the phenoxy compounds is however improved by taking into account the influence of the logP and/or the logD values on biol. activity. With the new combined method, the majority (8 out of 10) of the previously misclassified derivatives of phenoxy acetic acid are classified in accord with their bioassays. The recently determined crystal structure of the auxin-binding protein 1 (ABP1) enabled validation of our approach. The results of docking a few auxin related compounds with different biol. activity to ABP1 correlate well with the classification based on similarity of MIFs only. Biol. activity is, however, better predicted by a combined similarity of MIFs + logP/logD approach. In the experiment, the researchers used many compounds, for example, 2-(4-Methoxyphenoxy)acetic acid (cas: 1877-75-4HPLC of Formula: 1877-75-4).

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. 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.HPLC of Formula: 1877-75-4

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

Development of Photoactivated Fluorescent N-Hydroxyoxindoles and Their Application for Cell-Selective Imaging was written by Lai, Jinping;Yu, An;Yang, Letao;Zhang, Yixiao;Shah, Birju P.;Lee, Ki Bum. And the article was included in Chemistry – A European Journal in 2016.Name: 3-Methyl-4-nitroanisole This article mentions the following:

Photoactivatable fluorophores are essential tools for studying the dynamic mol. interactions within important biol. systems with high spatiotemporal resolution However, currently developed photoactivatable fluorophores based on conventional dyes have several limitations including reduced photoactivation efficiency, cytotoxicity, large mol. size, and complicated organic synthesis. To overcome these challenges, we herein report a class of photoactivatable fluorescent N-hydroxyoxindoles formed through the intramol. photocyclization of substituted o-nitrophenyl ethanol (ONPE). These oxindole fluorophores afford excellent photoactivation efficiency with ultra-high fluorescence enhancement (up to 800-fold) and are small in size. Furthermore, the oxindole derivatives show exceptional biocompatibility by generating water as the only photolytic side product. Moreover, structure-activity relationship anal. clearly revealed the strong correlation between the fluorescent properties and the substituent groups, which can serve as a guideline for the further development of ONPE-based fluorescent probes with desired photophys. and biol. properties. As a proof-of-concept, we demonstrated the capability of a new substituted ONPE that has an uncaging wavelength of 365-405 nm and an excitation/emission at 515 and 620 nm, for the selective imaging of a cancer cell line (Hela cells) and a human neural stem cell line (hNSCs). In the experiment, the researchers used many compounds, for example, 3-Methyl-4-nitroanisole (cas: 5367-32-8Name: 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. 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.Name: 3-Methyl-4-nitroanisole

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

Construction of Self-Reporting Biodegradable CO₂-Based Polycarbonates for the Visualization of Thermoresponsive Behavior with Aggregation-Induced Emission Technology was written by Wang, Molin;Wang, Enhao;Cao, Han;Liu, Shunjie;Wang, Xianhong;Wang, Fosong. And the article was included in Chinese Journal of Chemistry in 2021.Quality Control of 2-(2-Methoxyethoxy)ethanol This article mentions the following:

Thermoresponsive polymers with simultaneous biodegradability and signal “self-reporting” outputs that meet for advanced applications are hard to obtain. To address this issue, we developed fluorescence signal “self-reporting” biodegradable thermoresponsive polycarbonates through the immortal copolymerization of CO₂ and oligoethylene glycol monomethyl ether-functionalized epoxides in the presence of hydroxyl-modified tetraphenylethylene (TPE-OH). TPE-OH was used as chain transfer agent to afford well-defined polycarbonates with controlled mol. weight (6000-17000 g·mol^-1) and aggregation-induced emission characteristics. Through temperature-dependent fluorescence intensity study, low critical solution transition of TPE-labeled polycarbonates were determined and the fine details of thermal-induced phase transition process were monitored. Further research indicated that temperature-controlled aggregation and dissociation of TPE moieties are the main reason for fluorescence intensity variations. We anticipate that this work could offer a method to visualize the thermal transition process of thermoresponsive polycarbonates and broaden their application fields as smart materials. In the experiment, the researchers used many compounds, for example, 2-(2-Methoxyethoxy)ethanol (cas: 111-77-3Quality Control of 2-(2-Methoxyethoxy)ethanol).

2-(2-Methoxyethoxy)ethanol (cas: 111-77-3) 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.Quality Control of 2-(2-Methoxyethoxy)ethanol

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

Iron-catalyzed direct C-H arylation of heterocycles and quinones with arylboronic acids was written by Deb, Arghya;Manna, Srimanta;Maji, Arun;Dutta, Uttam;Maiti, Debabrata. And the article was included in European Journal of Organic Chemistry in 2013.COA of Formula: C9H10O4 This article mentions the following:

The arylation of C-H bonds to generate heteroaryl-aryl (Het-Ar) and arylated quinone (Quin-Ar) compounds has received great attention to achieve sustainable goals in synthetic chem. Despite significant advances, arylation of a broad range of Het-Ar and Quin-Ar derivatives remains a challenging task. Herein, a variety of heterocycles are arylated by using arylboronic acids in the presence of catalytic amounts of inexpensive Fe(NO₃)₃. The C-arylated quinone compounds can be prepared by reacting arylboronic acids with either quinone or hydroquinone. The present method is operationally simple, scalable, does not require prefunctionalization of the heterocycle or quinone, and can tolerate a wide variety of functional groups in the coupling partners. These qualities are expected to render this method attractive for academic and industrial use. In the experiment, the researchers used many compounds, for example, 2,3-Dimethoxy-5-methylcyclohexa-2,5-diene-1,4-dione (cas: 605-94-7COA of Formula: C9H10O4).

2,3-Dimethoxy-5-methylcyclohexa-2,5-diene-1,4-dione (cas: 605-94-7) 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).COA of Formula: C9H10O4

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

9-Benzylidene-9H-fluorene Derivatives Linked to Monoaza-15-crown-5: Synthesis and Metal Ion Sensing was written by Cao, Jing;Li, Yang;Feng, Junxiang. And the article was included in Chinese Journal of Chemistry in 2012.SDS of cas: 66943-05-3 This article mentions the following:

Two kinds of novel styryl chemosensory 2-FMNC and 3-FMNC, were designed and synthesized by an appropriate introduction of 9-benzylidene-9H-fluorene group as fluorophore with the aim at avoiding photoisomerization. These 9-benzylidene-9H-fluorene derivatives showed the similar selectivity and sensitivity upon addition of metal ions. The sensitivity of FMNC to alk. earth metal ions was Ba²⁺ > Sr²⁺ > Ca²⁺≈Mg²⁺. In the experiment, the researchers used many compounds, for example, 1,4,7,10-Tetraoxa-13-azacyclopentadecane (cas: 66943-05-3SDS of cas: 66943-05-3).

1,4,7,10-Tetraoxa-13-azacyclopentadecane (cas: 66943-05-3) 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 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.SDS of cas: 66943-05-3

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

Development of potent dopamine-norepinephrine uptake inhibitors (DNRIs) based on a (2S,4R,5R)-2-benzhydryl-5-((4-methoxybenzyl)amino)tetrahydro-2H-pyran-4-ol molecular template was written by Santra, Soumava;Sharma, Horrick;Vedachalam, Seenuvasan;Antonio, Tamara;Reith, Maarten;Dutta, Aloke. And the article was included in Bioorganic & Medicinal Chemistry in 2015.Application of 57179-35-8 This article mentions the following:

Current therapy of depression is less than ideal with remission rates of only 25-35% and response rates of 45-60%. It has been hypothesized that a dysfunctional dopaminergic system in the mesocorticolimbic pathway in depressive disorder may lead to development of anhedonia associated with loss of pleasure and interest along with loss of motivation. The current antidepressants do not address dopamine dysfunction which might explain their low efficacy. In this report, we have described an SAR study on our pyran-based triple reuptake inhibitors (TRIs) which are being investigated as the next-generation antidepressants. In the present work we demonstrate that our lead TRIs can be modified with appropriate aromatic substitutions to display a highly potent SSRI profile for compounds 2a and 4a (K_i (SERT); 0.71 and 2.68 nM, resp.) or a potent DNRI profile for compounds 6b and 6h (K_i (DAT/NET); 8.94/4.76 and 13/7.37 nM, resp.). Compounds 4g-4i exhibited potencies at all three monoamine transporters. The results provide insights into the structural requirements for developing selective dual- and triple-uptake inhibitors from a unique pyran mol. template for an effective management of depression and related disorders. In the experiment, the researchers used many compounds, for example, 3-Hydroxy-5-methoxybenzaldehyde (cas: 57179-35-8Application of 57179-35-8).

3-Hydroxy-5-methoxybenzaldehyde (cas: 57179-35-8) 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.Application of 57179-35-8

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

Identification of an Oxalamide Ligand for Copper-Catalyzed C-O Couplings from a Pharmaceutical Compound Library was written by Chan, Vincent S.;Krabbe, Scott W.;Li, Changfeng;Sun, Lijie;Liu, Yue;Nett, Alex J.. And the article was included in ChemCatChem in 2019.SDS of cas: 54916-28-8 This article mentions the following:

The use of pharmaceutical compound library approach in combination with high throughput screening to identify N,N’-bis(thiophene-2-ylmethyl)oxalamide as a ligand that was generally effective for copper-catalyzed C-O cross-couplings to prepare both biarylethers as well as phenols under mild conditions. In the experiment, the researchers used many compounds, for example, 1-(4-(4-Methoxyphenoxy)phenyl)ethanone (cas: 54916-28-8SDS of cas: 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 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.SDS of cas: 54916-28-8

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