Tag: 200-300

Efficient synthesis of 6-(hetero)arylthieno[3,2-b]pyridines by Suzuki-Miyaura coupling. Evaluation of growth inhibition on human tumor cell lines, SARs and effects on the cell cycle was written by Queiroz, Maria-Joao R. P.;Calhelha, Ricardo C.;Vale-Silva, Luis A.;Pinto, Eugenia;Lima, Raquel T.;Vasconcelos, M. Helena. And the article was included in European Journal of Medicinal Chemistry in 2010.Synthetic Route of C14H21BO4 This article mentions the following:

A wide variety of new bi(hetero)aryl derivatives of the thieno[3,2-b]pyridine skeleton was obtained in high to excellent yields (65-91%) by Suzuki-Miyaura cross-coupling of the Me 3-amino-6-bromothieno[3,2-b]pyridine-2-carboxylate, recently reported by us, with aryl or heteroaryl pinacolboranes or potassium trifluoroborates. The coupling products obtained were evaluated for their growth inhibitory effect on three human tumor cell lines, representing different tumor models, MCF-7 (breast adenocarcinoma), A375-C5 (melanoma) and NCI-H460 (non-small cell lung cancer). Some of the compounds showed an interesting activity against the tested cell lines, with GI₅₀ values in the 婵炴挾鎷?range, and it was possible to establish some structure-activity relationships (SARs). Several compounds presented GI₅₀ values below 15 婵炴挾鎷? particularly a bithiophene and an o-aniline thienopyridine derivative The first presented selectivity for MCF-7 and NCI-H460 cell lines, with very low GI₅₀ values (0.7-1.0 婵炴挾鎷?, while the latter was active against the three cell lines tested in this study, also presenting very low GI₅₀ values (2.5-4.2 婵炴挾鎷?. The effect of these two compounds on cell cycle progression was analyzed in the NCI-H460 cell line. Results showed that both compounds interfered with the normal cell cycle distribution. 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. Ethers can form hydrogen bonds with other molecules (alcohols, amines, etc.) that have O闂佺偨鍎插?or N闂佺偨鍎插?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.Synthetic Route of C14H21BO4

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

Formation of organometallic species from complexes of N-phenylaza-crown ether conjugates with lead cations in CID-MS/MS conditions was written by Franski, Rafal;Ogorek, Katarzyna;Gierczyk, Blazej. And the article was included in International Journal of Mass Spectrometry in 2017.Safety of 1,4,7,10-Tetraoxa-13-azacyclopentadecane This article mentions the following:

Gas phase decomposition of the ions [M + PbNO₃]⁺ (M stands for fluoro-substituted N-nitrophenylaza-crown ether conjugate), has been studied by the electrospray ionization-collision induced dissociation-tandem mass spectrometry (ESI-CID-MS/MS). The conjugates containing hydrogen atom at ortho position to the crown moiety, form abundant fragment ions which can be assigned as complexes of deprotonated conjugates and lead cation, thus the ions [M – H + Pb]⁺ (fragment ions formed as a result of HNO₃ loss). Interaction between the nitro group (present at the second ortho position to the crown moiety) and the metal cation affects the formation of fragment ion [M – H + Pb]⁺ (but does not prevent its formation). Ions [M – H + Pb]⁺ are very rare example of the organometallic species (containing metal-carbon bond), in which metal cation is also complexed by crown ether moiety. In the experiment, the researchers used many compounds, for example, 1,4,7,10-Tetraoxa-13-azacyclopentadecane (cas: 66943-05-3Safety of 1,4,7,10-Tetraoxa-13-azacyclopentadecane).

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. 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 1,4,7,10-Tetraoxa-13-azacyclopentadecane

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

Synthesis of monoazacrown ethers under phase-transfer catalysis was written by Luk’yanenko, N. G.;Basok, S. S.;Kulygina, E. Yu.;Bogashchenko, T. Yu.;Yakovenko, I. S.. And the article was included in Russian Journal of Organic Chemistry in 2012.Related Products of 66943-05-3 This article mentions the following:

A procedure was proposed for the synthesis of monoazacrown ethers by reaction of N-benzyldiethanolamine with oligo(ethylene glycol)-bis(p-toluene)sulfonates in a two-phase system aromatic hydrocarbon-50% aqueous alkali, followed by removal of the benzyl group by catalytic hydrogenolysis. The maximal yields of N-benzyl-aza-12-crown-4, -18-crown-6, and -21-crown-7 were achieved by adding 4-10 equiv of LiCl, BaBr₂, and CsCl, resp., to the reaction mixture, which probably indicated template effect. In the experiment, the researchers used many compounds, for example, 1,4,7,10-Tetraoxa-13-azacyclopentadecane (cas: 66943-05-3Related Products of 66943-05-3).

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, 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.Related Products of 66943-05-3

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

Copper(I)-catalyzed sulfonylative Suzuki-Miyaura cross-coupling was written by Chen, Yiding;Willis, Michael C.. And the article was included in Chemical Science in 2017.Category: ethers-buliding-blocks This article mentions the following:

By using a simple copper(I) catalyst a high yielding sulfonylative-Suzuki-Miyaura cross-coupling reaction was developed. The process provided a single step route to diaryl sulfones from the direct combination of arylboronic acids, sulfur dioxide and aryl iodides, and represents the first sulfonylative variant of a classic cross-coupling reaction. Sulfur dioxide was delivered from the surrogate reagent, DABSO. Variation of the reaction conditions allowed interruption of the sulfonylative-Suzuki coupling, resulted in the formation of a presumed Cu-sulfinate intermediate. These sulfinates was trapped as their sodium salts and treated with electrophiles to allow access to arylalkyl sulfones, 閻?hydroxyl sulfones, sulfonamides and sulfonyl fluorides. In the experiment, the researchers used many compounds, for example, (4-((4-Methoxybenzyl)oxy)phenyl)boronic acid (cas: 156635-90-4Category: ethers-buliding-blocks).

(4-((4-Methoxybenzyl)oxy)phenyl)boronic acid (cas: 156635-90-4) 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.Category: ethers-buliding-blocks

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

Metal-Free Photoinduced Transformation of Aryl Halides and Diketones into Aryl Ketones was written by Yao, Qiuli;Liu, Wenbo;Liu, Peng;Ren, Linjing;Fang, Xuehong;Li, Chao-Jun. And the article was included in European Journal of Organic Chemistry in 2019.SDS of cas: 75581-11-2 This article mentions the following:

The acylation of aryl halides to prepare aryl ketones without metal catalyst represents an important yet challenging topic towards more sustainable ketone synthesis. A simple and efficient metal-free protocol for the acylation of aryl halides with diketone under the irradiation of light utilizing N-methylpiperidine as base under an air atm. is described. This reaction can tolerate a wide range of functional groups and the corresponding ketones can be obtained in modest to good yields. In the experiment, the researchers used many compounds, for example, 4-Iodo-1-methoxy-2-methylbenzene (cas: 75581-11-2SDS of cas: 75581-11-2).

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

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

Synthesis and Characterization of Hexapole [7]Helicene, A Circularly Twisted Chiral Nanographene was written by Zhu, Yanpeng;Xia, Zeming;Cai, Zeying;Yuan, Ziyong;Jiang, Nianqiang;Li, Tao;Wang, Yonggen;Guo, Xiaoyu;Li, Zhihao;Ma, Shuang;Zhong, Dingyong;Li, Yang;Wang, Jiaobing. And the article was included in Journal of the American Chemical Society in 2018.Quality Control of 2-(3,5-Dimethoxyphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane This article mentions the following:

The synthesis and characterization of two hexapole [7]helicenes (H7Hs) is reported. Single crystal X-ray diffraction unambiguously confirms the mol. structure. H7H absorbs light, with distinct Cotton effect, from UV to the near-IR (濞?sup>max = 618 nm). Cyclic voltammetry reveals nine reversible redox states, consecutively from -2 to +6. These chiroptical and electronic properties of H7H are inaccessible from helicene’s small homologues. In the experiment, the researchers used many compounds, for example, 2-(3,5-Dimethoxyphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (cas: 365564-07-4Quality Control of 2-(3,5-Dimethoxyphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane).

2-(3,5-Dimethoxyphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (cas: 365564-07-4) 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. 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-(3,5-Dimethoxyphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

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

Gas-liquid chromatographic analysis of the OPSM flotation agent was written by Kosenko, N. N.;Baranova, G. F.;Gurvich, S. M.. And the article was included in Zhurnal Prikladnoi Khimii (Sankt-Peterburg, Russian Federation) in 1968.Product Details of 20324-33-8 This article mentions the following:

OPSM (I) flotation agent is manufactured by condensation of MeOH with propylene oxide. Me ethers of mono-, di-, tri-, tetra-, and pentapropylene glycol present in crude I were determined by gas chromatog. at 210闁?in 1-m. 闁?4-mm. column filled with Teflon containing 5% E-301 elastomer, with 1 cc. H/sec. as carrier gas. The sensitivity of the method is 0.1%, and the relative error is <10%. 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. 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.Product Details of 20324-33-8

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

Tautocrowns: a concept for a sensing molecule with an active side-arm was written by Antonov, Liudmil M.;Kurteva, Vanya B.;Simeonov, Svilen P.;Deneva, Vera V.;Crochet, Aurelien;Fromm, Katharina M.. And the article was included in Tetrahedron in 2010.Name: 1,4,7,10-Tetraoxa-13-azacyclopentadecane This article mentions the following:

A new sensing mol. containing aza-15-crown-5 as a receptor and 4-(phenyldiazenyl)naphthalen-1-ol as a signal converter has been synthesized. In the free ligand, the hydrogen bonding between the tautomeric OH group and the nitrogen atom from the macrocycle fully shifts the tautomeric equilibrium towards the enol form. The complexation reverses the equilibrium as a result of the strong interaction between the metal ion captured in the macrocyclic moiety and the tautomeric carbonyl group. The complex formation is accompanied by strong bathochromic (between 60 and 100 nm) and hyperchromic effects on the absorption spectra. Obviously, the tautomeric OH/C=O groups play the role of an active side-arm in the complexation, supporting it via formation of a 3D cavity and giving possibility for ejection of the guest compound under stimuli to shift the tautomeric process back. 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. 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).Name: 1,4,7,10-Tetraoxa-13-azacyclopentadecane

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

High-frame-rate liquid crystal phase modulator for augmented reality displays was written by Chen, Ran;Huang, Yuge;Li, Jian;Hu, Minggang;Li, Juanli;Chen, Xinbing;Chen, Pei;Wu, Shin-Tson;An, Zhongwei. And the article was included in Liquid Crystals in 2019.Electric Literature of C18H18O This article mentions the following:

We optimize a new liquid crystal mixture with wide nematic range, high birefringence (铻杗), high resistivity, moderate dielec. anisotropy (铻栬敋) and relatively low rotational viscosity for augmented reality display applications. High 铻杗 and large 铻栬敋 allow a thin cell gap (d 閳?1.5 娓璵) to be employed in a reflective liquid-crystal-on-silicon (LCoS) device to achieve 2锜?phase change at 5 V and 2.87 ms average phase-to-phase response time at 40鎺矯 without complicated overdrive circuitry. Such a fast response time enables an LCoS panel to achieve 240 Hz frame rate for field sequential color operation to avoid image flickering. In the experiment, the researchers used many compounds, for example, 1-Methoxy-4-((4-propylphenyl)ethynyl)benzene (cas: 39969-26-1Electric Literature of C18H18O).

1-Methoxy-4-((4-propylphenyl)ethynyl)benzene (cas: 39969-26-1) 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. 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 C18H18O

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

Reusable Pd-PolyHIPE for Suzuki-Miyaura Coupling was written by Ravbar, Miha;Koler, Amadeja;Paljevac, Muzafera;Krajnc, Peter;Kolar, Mitja;Iskra, Jernej. And the article was included in ACS Omega in 2022.COA of Formula: C14H15BO4 This article mentions the following:

Palladium was immobilized on a highly porous copolymer of 4-vinylpyridine and divinylbenzene (polyHIPE-poly(high internal phase emulsion)) using palladium(II) acetate to obtain PolyPy-Pd with 6.1 wt % or 0.57 mmol Pd/g. The immobilized catalyst was able to catalyze the coupling of iodobenzene and phenylboronic acid in ethylene glycol monomethyl ether/water (3:1) within 4 h at rt and complete conversion was observed when 2.5 mol % of Pd per PhI was used. The reaction tolerated a wide range of substituents on the aromatic ring. Iodobenzene derivatives with electron-withdrawing substituents showed higher reactivity, while the opposite was true for the phenylboronic acid series. The polyHIPE-supported Pd catalyst was also used for the direct conversion of phenylboronic acid to biphenyl through an iodination/coupling reaction sequence. The recyclability of the heterogeneous catalyst was also optimized, and by finding a suitable combination of solvents for the loading of Pd, the reaction, and the isolation of the product, the solid-supported catalyst was completely regenerated and used in the next reaction with the same activity. In the experiment, the researchers used many compounds, for example, (4-((4-Methoxybenzyl)oxy)phenyl)boronic acid (cas: 156635-90-4COA of Formula: C14H15BO4).

(4-((4-Methoxybenzyl)oxy)phenyl)boronic acid (cas: 156635-90-4) 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.COA of Formula: C14H15BO4

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