Tag: 100-200

Synthetic studies on indoles and related compounds. 49. Unexpected formation of quinolone derivatives in Reissert indole synthesis was written by Suzuki, Hideharu;Gyoutoku, Hiroshi;Yokoo, Hiroe;Shinba, Mika;Sato, Yuka;Yamada, Hiroshi;Murakami, Yasuoki. And the article was included in Synlett in 2000.Quality Control of 3-Methyl-4-nitroanisole This article mentions the following:

The Reissert indole synthesis was found to unexpectedly give 3-hydroxy-1,2,3,4-tetrahydro-2-quinolone derivatives I (R = H, 6-MeO, 5-MeO, 3-CO₂Et, 3-Me, 3-MeO, 3-Me₂CHO), sometimes in a high ratio to the expected Et indole-2-carboxylate derivatives, depending on the conditions of the catalytic reduction of the intermediate (2-nitrophenyl)pyruvates. This reactivity is characteristic in the preparation of 7-substituted indoles. In the experiment, the researchers used many compounds, for example, 3-Methyl-4-nitroanisole (cas: 5367-32-8Quality Control of 3-Methyl-4-nitroanisole).

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

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Phosphorylated cyclopropanes in the synthesis of α-alkylidene-γ-butyrolactones: total synthesis of (±)-savinin, (±)-gadain and (±)-peperomin E was written by Lloyd, Matthew G.;Taylor, Richard J. K.;Unsworth, William P.. And the article was included in Organic & Biomolecular Chemistry in 2016.Formula: C11H16O3 This article mentions the following:

Phosphorylated cyclopropanes, generated via the Rh(II)-catalyzed intramol. cyclopropanation of α-(diethoxyphosphoryl)acetates, have been found to be useful precursors in the synthesis of α-alkylidene-γ-butyrolactones. These cyclopropyl intermediates undergo regioselective reductive ring-opening and subsequent Horner-Wadsworth-Emmons olefination to complete the synthesis. Total syntheses of (±)-savinin (I) and (±)-gadain (II), as well as the first total synthesis of (±)-peperomin E (III), are all described using this method. In the experiment, the researchers used many compounds, for example, 3-(3,4-Dimethoxyphenyl)propan-1-ol (cas: 3929-47-3Formula: C11H16O3).

3-(3,4-Dimethoxyphenyl)propan-1-ol (cas: 3929-47-3) 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. 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.Formula: C11H16O3

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Disilanes as oxygen scavengers and surrogates of hydrosilanes suitable for selective reduction of nitroarenes, phosphine oxides and other valuable substrates was written by Gevorgyan, Ashot;Mkrtchyan, Satenik;Grigoryan, Tatevik;Iaroshenko, Viktor O.. And the article was included in Organic Chemistry Frontiers in 2017.Computed Properties of C8H9NO3 This article mentions the following:

In this report, the reaction of nitroarenes RNO₂ (R = Pr, cyclohexyl, 2-methylphenyl, pyridin-3-yl, etc.) with hexamethyldisilane under various conditions affords a different range of compounds with excellent selectivity. In particular, the reaction of nitroarenes with hexamethyldisilane using a CsF/TBAB/toluene system provides suitable azo compounds, while in the presence of a CsF/TBAB/[Pd]/EtOH system this hexamethyldisilane acts as a novel surrogate of gaseous trimethylsilane, thus, reducing nitroarenes to corresponding anilines RNH₂. The synthetic value of the developed methodol. was further extended by the reduction of a wide range of substrates including N-oxides such as 2-methyl-quinoline-1-oxide, isoquinoline-2-oxide, 2,6-dimethylpyridine-1-oxide, 2-phenylpyridine-1-oxide, sulfoxides such as methanesulfinylbenzene, (benzenesulfinyl)benzene, 1-methanesulfinyl-4-methylbenzene, [(phenylmethane)sulfinylmethyl]benzene, phosphine oxides such as [[(diphenylphosphoroso)methyl](phenyl)phosphoryl]benzene, [[3-(diphenylphosphoroso)propyl](phenyl)phosphoryl]benzene, (diphenylphosphoryl)benzene, etc. In the experiment, the researchers used many compounds, for example, 3-Methyl-4-nitroanisole (cas: 5367-32-8Computed Properties of C8H9NO3).

3-Methyl-4-nitroanisole (cas: 5367-32-8) 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 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.Computed Properties of C8H9NO3

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Structural basis for gating mechanisms of a eukaryotic P-glycoprotein homolog was written by Kodan, Atsushi;Yamaguchi, Tomohiro;Nakatsu, Toru;Sakiyama, Keita;Hipolito, Christopher J.;Fujioka, Akane;Hirokane, Ryo;Ikeguchi, Keiji;Watanabe, Bunta;Hiratake, Jun;Kimura, Yasuhisa;Suga, Hiroaki;Ueda, Kazumitsu;Kato, Hiroaki. And the article was included in Proceedings of the National Academy of Sciences of the United States of America in 2014.Related Products of 3929-47-3 This article mentions the following:

P-glycoprotein is an ATP-binding cassette multidrug transporter that actively transports chem. diverse substrates across the lipid bilayer. The precise mol. mechanism underlying transport is not fully understood. Here, the authors present crystal structures of a eukaryotic P-glycoprotein homolog, CmABCB1 with ATPase activity from Cyanidioschyzon merolae, in 2 forms: unbound at 2.6-Å resolution and bound to a unique allosteric peptide inhibitor at 2.4-Å resolution The inhibitor clamped the transmembrane helixes from the outside, fixing the CmABCB1 structure in an inward-open conformation similar to the unbound structure, confirming that an outward-opening motion is required for the ATP hydrolysis cycle. These structures, along with site-directed mutagenesis and transporter activity measurements, revealed the detailed architecture of the transporter, including a gate that opens to extracellular side and 2 gates that open to intramembranous region and the cytosolic side. The authors propose that the motion of the nucleotide-binding domain drives those gating apparatuses via 2 short intracellular helixes, IH1 and IH2, and 2 transmembrane helixes, TM2 and TM5. In the experiment, the researchers used many compounds, for example, 3-(3,4-Dimethoxyphenyl)propan-1-ol (cas: 3929-47-3Related Products of 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. 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.Related Products of 3929-47-3

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Ether | (C2H5)2O – PubChem

Design, synthesis and molecular docking of amide and urea derivatives as Escherichia coli PDHc-E1 inhibitors was written by He, Jun-Bo;Ren, Yan-Liang;Sun, Qiu-Shuang;You, Ge-Yun;Zhang, Li;Zou, Peng;Feng, Ling-Ling;Wan, Jian;He, Hong-Wu. And the article was included in Bioorganic & Medicinal Chemistry in 2014.Application In Synthesis of 2-(4-Methoxyphenoxy)acetic acid This article mentions the following:

By targeting the ThDP binding site of Escherichia coli PDHc-E1, two new ‘open-chain’ classes of E. coli PDHc-E1 inhibitors, amide and urea derivatives, were designed, synthesized, and evaluated. The amide derivative I showed the most potent inhibition of E. coli PDHc-E1. The urea derivatives displayed more potent inhibitory activity than the corresponding amide derivatives with the same substituent. Mol. docking studies confirmed that the urea derivatives have more potency due to the two hydrogen bonds formed by two NH of urea with Glu522. The docking results also indicate it might help us to design more efficient PDHc-E1 inhibitors that could interact with Glu522. In the experiment, the researchers used many compounds, for example, 2-(4-Methoxyphenoxy)acetic acid (cas: 1877-75-4Application In Synthesis 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, 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. 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-(4-Methoxyphenoxy)acetic acid

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Ether – Wikipedia,
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Transition-Metal-Free Alkylative Aromatization of Tetralones using Alcohols/Amino Alcohols Toward the Synthesis of Bioactive Naphthol and Benzo[e/g]indole Derivatives was written by Ubale, Akash S.;Londhe, Gokul S.;Shaikh, Moseen A.;Gnanaprakasam, Boopathy. And the article was included in Journal of Organic Chemistry in 2022.Name: (4-Methoxyphenyl)methanol This article mentions the following:

Herein, the synthesis of bioactive naphthols I (R¹ = H, 6-Br, 6-MeO, 7-MeO; R² = Ph, 3-MeC₆H₄, 2-thienyl, etc.) and II or benzindoles III (R³ = Me, Et, PhCH₂, etc.) and IV by alkylative aromatization of the corresponding 1- and 2-tetralones with alcs. R²CH₂OH or amino alcs. H₂NCHR³CH₂OH in the presence of NaOH using aerobic oxidative cross-coupling protocol is reported. This is a general and transition-metal-free method, which uses an inexpensive base, does not require inert conditions, and furnishes water and hydrogen peroxide as byproducts. Moreover, this method is compatible with a wide substrate scope and showed exclusive regioselectivity. In the experiment, the researchers used many compounds, for example, (4-Methoxyphenyl)methanol (cas: 105-13-5Name: (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 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.Name: (4-Methoxyphenyl)methanol

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Microwave-assisted O-alkylation of carboxylic acids in dry media: Expeditious synthesis of 2-Oxo-2-arylethyl carboxylates was written by Li, Z.;Quan, Z. J.;Wang, X. C.. And the article was included in Chemical Papers in 2004.Reference of 1877-75-4 This article mentions the following:

Microwave-assisted O-alkylation reactions of carboxylic acids, such as aryloxyacetic acids, 4-chlorobenzoic acid, (un)substituted furoic acids, and benzofuroic acid, with (un)substituted ω-haloacetophenones in dry media under phase-transfer catalysis are described. 2-Oxo-2-arylethyl carboxylates are expeditiously synthesized by this method in high yield using Bu₄NBr as catalyst. In the experiment, the researchers used many compounds, for example, 2-(4-Methoxyphenoxy)acetic acid (cas: 1877-75-4Reference of 1877-75-4).

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, 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.Reference of 1877-75-4

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

Neotropical ant gardens: I. Chemical constituents was written by Seidel, J. L.;Epstein, W. W.;Davidson, D. W.. And the article was included in Journal of Chemical Ecology in 1990.Computed Properties of C8H8O3 This article mentions the following:

In ant gardens of lowland Amazonia, parabiotic ant species Camponotus femoratus and Crematogaster cf. limata parabiotica cultivate a taxonomically diverse group of epiphtic plants, whose establishment is restricted to arboreal carton ant nests. Epiphyte seeds are collected by workers of C. femoratus, the larger of the 2 ants, and stored unharmed in brood chambers where they subsequently germinate. Although seeds of some ant-garden epiphytes bear nutritional rewards, previous studies have shown that these rewards are not sufficient to explain the pattern of ant attraction to seeds. Five aromatic compounds occur frequently in and on the seeds of most ant garden epiphytes and may be chem. cues by which ants recognize propagules of their symbiotic plants. The most widely distributed of these is Me 6-methylsalicylate (6-MMS), previously reported as a major mandibular gland product in related Camponotus species and present in trace quantities in C. femoratus males. (-)-Citronellol (previously unreported in Camponotus) was the principal volatile constituent in extracts of male heads, and (-)-mellein was present in small quantities. Discovery of 6-MMS inside the mandibular glands of male C. femoratus (and its presence in analogous glands of related ants) offers preliminary support for Ule’s (1906) hypothesis that seeds attract ants by mimicking ant brood. In addition, the likely fungistatic activity of seed compounds suggests that they could retard microbial pathogens of ants and plants in the organic detritus of nest gardens. While the presence of identical seed compounds in so many unrelated plant lineages might represent a remarkable case of convergent evolution, other interpretations are possible. In the experiment, the researchers used many compounds, for example, 3-Hydroxy-5-methoxybenzaldehyde (cas: 57179-35-8Computed Properties of C8H8O3).

3-Hydroxy-5-methoxybenzaldehyde (cas: 57179-35-8) 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).Computed Properties of C8H8O3

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

Photodynamic Therapy Directed by Three-Photon Active Rigid Plane Organic Photosensitizer was written by Cao, Hongzhi;Fang, Bin;Liu, Jiejie;Shen, Yu;Shen, Jie;Xiang, Pan;Zhou, Qin;De Souza, Senio Campos;Li, Dandan;Tian, Yupeng;Luo, Lei;Zhang, Zhongping;Tian, Xiaohe. And the article was included in Advanced Healthcare Materials in 2021.Recommanded Product: 111-77-3 This article mentions the following:

Multi-photon photosensitizers (PSs) could significantly improve the efficacy of photodynamic therapy due to the long-wavelength favorability for deeper tissue penetration and lower biol. damage. However, most studies are limited to single-photon or two-photon PSs at a relatively short-wave excitation window. To overcome this barrier, we rationally design a series of rigid plane compounds with efficient reactive oxygen species (ROS) production in vitro under laser irradiation Furthermore, the studies show that one of the compounds (U-TsO) could induce rapid multi-types of cell death under three-photon exposure, suggesting a promising clin. outcome in ex vivo 3D multicellular tumor spheroid. This work offers a novel strategy to construct functional materials with competitive multi-photon photodynamic therapy (PDT) outcome. In the experiment, the researchers used many compounds, for example, 2-(2-Methoxyethoxy)ethanol (cas: 111-77-3Recommanded Product: 111-77-3).

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

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Microwave irradiation of lignocellulosic materials V. Effects of microwave irradiation on enzymic susceptibility of crystalline cellulose was written by Azuma, Junichi;Asai, Toshihiro;Isaka, Masao;Koshijima, Tetsuo. And the article was included in Journal of Fermentation Technology in 1985.Application In Synthesis of 3-(3,4-Dimethoxyphenyl)propan-1-ol This article mentions the following:

The usefulness of various treatments was compared in the enzymic saccharification of microwave-irradiated crystalline cellulose (Whatman CF11). The variations include the extent of enzymic saccharification, the treatment temperature suitable for enzymic saccharification, and the effects of AcOH, lignin, and monomeric lignin model compounds on the extent of enzymic saccharification. The effects of microwave irradiation alone were evaluated. When cellulose suspended in water was heated above 180°, partial acid hydrolysis occurred. The extent of hydrolysis increased with an increase in temperature but did not exceed 3% even at 235°, where 0.03 mequiv of acid and cellooligosaccharides having a d.p. of 2-6 as well as glucose were produced. Although the presence of AcOH increased reducing sugar production by a factor of 2.2-3.8, lignin did not induce degradation of cellulose. The extent of enzymic saccharification of cellulose was greatly enhanced by microwave irradiation pretreatment in the presence of water above 220° and reached 43.2% at 240° at cellulose and enzyme concentrations of 2.0 and 0.2%, resp. The presence of AcOH facilitated the enzymic susceptibility and the extent of saccharification reached 69.2% at 240°. Lignin also facilitated the enzymic susceptibility but its action was limited to temperatures below 200°, above which lignin inhibited enzymic attack. The enhancement of the enzymic susceptibility by lignin was further promoted by the addition of AcOH. In this case, the maximal extent of saccharification was 41.5% at 200°, indicating that the temperature needed to reach 42-43% saccharification could be lowered for 40° by a synergistic effect between lignin and AcOH. Combinations of AcOH and monomeric lignin model compounds also show synergistic effects. However, lignin model compounds did not inhibit the enzyme reaction above 200° in contrast to the case of lignin. An unsaturated C-C double bond in the substituent of benzene ring seems to be important in the synergistic effect, whereas phenolic OH groups are of minor importance. In the experiment, the researchers used many compounds, for example, 3-(3,4-Dimethoxyphenyl)propan-1-ol (cas: 3929-47-3Application In Synthesis of 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. 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 3-(3,4-Dimethoxyphenyl)propan-1-ol

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