Category: ethers-buliding-blocks

Huang, Lin published the artcileRuthenium-Catalyzed Dehydrogenation Through an Intermolecular Hydrogen Atom Transfer Mechanism, Safety of 2-Methoxynaphthalene, the publication is Angewandte Chemie, International Edition (2021), 60(13), 7290-7296, database is CAplus and MEDLINE.

The direct dehydrogenation of alkanes is among the most efficient ways to access valuable alkene products. Although several catalysts have been designed to promote this transformation, they have unfortunately found limited applications in fine chem. synthesis. Here, we report a conceptually novel strategy for the catalytic, intermol. dehydrogenation of alkanes using a ruthenium catalyst. The combination of a redox-active ligand and a sterically hindered aryl radical intermediate has unleashed this novel strategy. Importantly, mechanistic investigations have been performed to provide a conceptual framework for the further development of this new catalytic dehydrogenation system.

Angewandte Chemie, International Edition published new progress about 93-04-9. 93-04-9 belongs to ethers-buliding-blocks, auxiliary class Naphthalene,Ether, name is 2-Methoxynaphthalene, and the molecular formula is C11H10O, Safety of 2-Methoxynaphthalene.

Referemce:
https://en.wikipedia.org/wiki/Ether,
Ether | (C2H5)2O – PubChem

Elamin, Khalid published the artcileGlass transition and relaxation dynamics of propylene glycol-water solutions confined in clay, Related Products of ethers-buliding-blocks, the publication is Journal of Chemical Physics (2014), 141(3), 034505/1-034505/8, database is CAplus and MEDLINE.

The mol. dynamics of aqueous solutions of propylene glycol (PG) and propylene glycol methylether (PGME) confined in a two-dimensional layer-structured Na-vermiculite clay has been studied by broadband dielec. spectroscopy and differential scanning calorimetry. As typical for liquids in confined geometries the intensity of the cooperative α-relaxation becomes considerably more suppressed than the more local β-like relaxation processes. In fact, at high water contents the calorimetric glass transition and related structural α-relaxation cannot even be observed, due to the confinement. Thus, the intensity of the viscosity related α-relaxation is dramatically reduced, but its time scale as well as the related glass transition temperature T_g are for both systems only weakly influenced by the confinement. In the case of the PGME-water solutions it is an important finding since in the corresponding bulk system a pronounced non-monotonic concentration dependence of the glass transition related dynamics has been observed due to the growth of hydrogen bonded relaxing entities of water bridging between PGME mols. [J. Sjostrom, J. Mattsson, R. Bergman, and J. Swenson, Phys. Chem. B 115, 10013 (2011)]. The present results suggest that the same type of structural entities are formed in the quasi-two-dimensional space between the clay platelets. It is also observed that the main water relaxation cannot be distinguished from the β-relaxation of PG or PGME in the concentration range up to intermediate water contents. This suggests that these two processes are coupled and that the water mols. affect the time scale of the β-relaxation. However, this is most likely true also for the corresponding bulk solutions, which exhibit similar time scales of this combined relaxation process below T_g. Finally, it is found that at higher water contents the water relaxation does not merge with, or follow, the α-relaxation above T_g, but instead crosses the α-relaxation, indicating that the two relaxation processes are independent of each other. This can only occur if the two processes do not occur in the same parts of the confined solutions Most likely the hydration shell of the interlayer Na⁺ ions is causing this water relaxation, which does not participate in the α-relaxation at any temperature (c) 2014 American Institute of Physics.

Journal of Chemical Physics published new progress about 1589-47-5. 1589-47-5 belongs to ethers-buliding-blocks, auxiliary class Aliphatic hydrocarbon chain,Alcohol,Ether, name is 2-Methoxypropan-1-ol, and the molecular formula is C4H10O2, Related Products of ethers-buliding-blocks.

Referemce:
https://en.wikipedia.org/wiki/Ether,
Ether | (C2H5)2O – PubChem

Le Roux, Antoine published the artcileStructure-Permeability Relationship of Semipeptidic Macrocycles-Understanding and Optimizing Passive Permeability and Efflux Ratio, Recommanded Product: (S)-2-((((9H-Fluoren-9-yl)methoxy)carbonyl)(methyl)amino)-3-phenylpropanoic acid, the publication is Journal of Medicinal Chemistry (2020), 63(13), 6774-6783, database is CAplus and MEDLINE.

We herein report the first thorough anal. of the structure-permeability relationship of semipeptidic macrocycles. In total, 47 macrocycles were synthesized using a hybrid solid-phase/solution strategy, and then their passive and cellular permeability was assessed using the parallel artificial membrane permeability assay (PAMPA) and Caco-2 assay, resp. The results indicate that semipeptidic macrocycles generally possess high passive permeability based on the PAMPA, yet their cellular permeability is governed by efflux, as reported in the Caco-2 assay. Structural variations led to tractable structure-permeability and structure-efflux relationships, wherein the linker length, stereoinversion, N-methylation, and peptoids site-specifically impact the permeability and efflux. Extensive NMR, mol. dynamics, and ensemble-based three-dimensional polar surface area (3D-PSA) studies showed that ensemble-based 3D-PSA is a good predictor of passive permeability.

Journal of Medicinal Chemistry published new progress about 77128-73-5. 77128-73-5 belongs to ethers-buliding-blocks, auxiliary class Inhibitor, name is (S)-2-((((9H-Fluoren-9-yl)methoxy)carbonyl)(methyl)amino)-3-phenylpropanoic acid, and the molecular formula is C25H23NO4, Recommanded Product: (S)-2-((((9H-Fluoren-9-yl)methoxy)carbonyl)(methyl)amino)-3-phenylpropanoic acid.

Referemce:
https://en.wikipedia.org/wiki/Ether,
Ether | (C2H5)2O – PubChem

Hanessian, Stephen published the artcileAlternative and Expedient Asymmetric Syntheses of L-(+)-Noviose, Synthetic Route of 99438-28-5, the publication is Organic Letters (2008), 10(2), 261-264, database is CAplus and MEDLINE.

L-(+)-Noviose I, the sugar component of the antibiotic novobiocin, was synthesized from either 2,2-dimethyl-1,3-cyclopentadione or benzyl glyoxylate relying on stoichiometric and asym. processes by two independent methods, comprising six and nine steps, in 27 and 20% overall yields, resp. An unsaturated lactone II was prepared via stereoselective boron-catalyzed reduction, scandium-catalyzed Baeyer-Villiger oxidation and Saegusa oxidation from 2,2-dimethyl-1,3-cyclopentadione. II could also be prepared via stereoselective Brown allylation, ruthenium-catalyzed isomerization and ring-closing metathesis, and allylic oxidation from benzyl glyoxylate. II was then transformed to I via stereoselective reduction and dihydroxylation.

Organic Letters published new progress about 99438-28-5. 99438-28-5 belongs to ethers-buliding-blocks, auxiliary class Chiral,Aliphatic cyclic hydrocarbon, name is (+)-B-Methoxydiisopinocampheylborane, and the molecular formula is C21H37BO, Synthetic Route of 99438-28-5.

Referemce:
https://en.wikipedia.org/wiki/Ether,
Ether | (C2H5)2O – PubChem

Lemarchand, Aude published the artcileSynthesis of chiral ansa-bridged macrocyclic lactams ([16]metacyclophanes) related to geldanamycin, Computed Properties of 99438-28-5, the publication is Synthesis (2005), 1977-1990, database is CAplus.

Two chiral ansa-bridged lactams ([16]metacyclophanes) I (X = CH₂, O) were synthesized starting from 2-methoxyhydroquinone diisopropyl ether in 14 (I, X = CH₂, 3.9% overall) and 16 synthetic steps (I X = O, 0.6% overall). Both compounds contain typical features of geldanamycin in the C-1 to C-9 part of the ansa chain, i.e. the α,β,γ,δ-unsaturated anilide (C-1 to C-5), the carbamate at the stereogenic carbon atom C-7 and the E-double bond between C-8 and C-9. While the rest of the ansa chain (C-10 to C-15) was an alkyl chain in compound I (X = CH₂), a more polar CH₂OCH₂CH₂OCH₂ chain was installed in compound I (X = O). Key step of the sequence was a ring-closing metathesis in which the ansa compounds were formed as a mixture of isomers. Deprotection and oxidation to the quinone failed for diisopropyl ether I (X = O) but was successfully conducted with precursor I (X = CH₂).

Synthesis published new progress about 99438-28-5. 99438-28-5 belongs to ethers-buliding-blocks, auxiliary class Chiral,Aliphatic cyclic hydrocarbon, name is (+)-B-Methoxydiisopinocampheylborane, and the molecular formula is C21H37BO, Computed Properties of 99438-28-5.

Referemce:
https://en.wikipedia.org/wiki/Ether,
Ether | (C2H5)2O – PubChem

Vincent, Andrea published the artcileIdentification of candidate drugs for the treatment of ALS, Related Products of ethers-buliding-blocks, the publication is Amyotrophic Lateral Sclerosis and Other Motor Neuron Disorders (2005), 6(1), 29-36, database is CAplus and MEDLINE.

A consortium of investigators interested in neurodegenerative diseases collaborated to screen 1040 drugs in multiple neurodegenerative disease assays. One model of amyotrophic lateral sclerosis (ALS) pathogenesis in particular incorporated glutamate exposure in enriched primary rat motor neuron cultures. In this model 78 compounds decreased motor neuron death caused by 100 μM glutamate. Almost all these pharmacol. agents act at one or more of the following cellular targets: (1) protein synthesis inhibition; (2) Cox inhibition; (3) regulation of anion flux; (4) modulation of GABA receptors; (5) antioxidant, and (6) cell cycle inhibition. The most prevalent mode of action was the regulation of intracellular calcium. These data extend the understanding of motor neuron degeneration and identify a number of cellular targets for the improvement of combined therapies for neurodegenerative disease.

Amyotrophic Lateral Sclerosis and Other Motor Neuron Disorders published new progress about 637-58-1. 637-58-1 belongs to ethers-buliding-blocks, auxiliary class Inhibitor, name is 4-(3-(4-Butoxyphenoxy)propyl)morpholine hydrochloride, and the molecular formula is C42H63O3P, Related Products of ethers-buliding-blocks.

Referemce:
https://en.wikipedia.org/wiki/Ether,
Ether | (C2H5)2O – PubChem

Anderson, Nichole published the artcileProcedure for the rapid synthesis of the monomer 1,4-bis(chloromethyl)-2-(2-ethylhexyloxy)-5-methoxybenzene, Category: ethers-buliding-blocks, the publication is Synthetic Communications (2008), 38(22), 3903-3908, database is CAplus.

The alkylation of 4-methoxyphenol with 2-ethylhexyl bromide was accelerated by using potassium tert-butoxide in DMF. Subsequent chloromethylation occurred quickly using acetic acid as a cosolvent to give the monomer (for MEH-PPV) in 61% overall yield on a 2-mol scale.

Synthetic Communications published new progress about 146370-51-6. 146370-51-6 belongs to ethers-buliding-blocks, auxiliary class Benzene,Ether, name is 1-((2-Ethylhexyl)oxy)-4-methoxybenzene, and the molecular formula is C15H24O2, Category: ethers-buliding-blocks.

Referemce:
https://en.wikipedia.org/wiki/Ether,
Ether | (C2H5)2O – PubChem

Micewicz, Ewa D. published the artcileSmall lipidated anti-obesity compounds derived from neuromedin U, Application of (S)-2-((((9H-Fluoren-9-yl)methoxy)carbonyl)(methyl)amino)-3-phenylpropanoic acid, the publication is European Journal of Medicinal Chemistry (2015), 616-626, database is CAplus and MEDLINE.

A small library of truncated/lipid-conjugated neuromedin U (NmU) analogs was synthesized and tested in vitro using an intracellular calcium signaling assay. The selected, most active analogs were then tested in vivo, and showed potent anorexigenic effects in a diet-induced obese (DIO) mouse model. The most promising compound, NM4-C₁₆ was effective in a once-weekly-dose regimen. Collectively, the authors’ findings suggest that short, lipidated analogs of NmU are suitable leads for the development of novel anti-obesity therapeutics.

European Journal of Medicinal Chemistry published new progress about 77128-73-5. 77128-73-5 belongs to ethers-buliding-blocks, auxiliary class Inhibitor, name is (S)-2-((((9H-Fluoren-9-yl)methoxy)carbonyl)(methyl)amino)-3-phenylpropanoic acid, and the molecular formula is C25H23NO4, Application of (S)-2-((((9H-Fluoren-9-yl)methoxy)carbonyl)(methyl)amino)-3-phenylpropanoic acid.

Referemce:
https://en.wikipedia.org/wiki/Ether,
Ether | (C2H5)2O – PubChem

Annunziatini, Claudia published the artcileAryl substituted N-hydroxyphthalimides as mediators in the laccase-catalyzed oxidation of lignin model compounds and delignification of wood pulp, Product Details of C16H18O4, the publication is Journal of Molecular Catalysis B: Enzymatic (2005), 32(3), 89-96, database is CAplus.

Aryl substituted N-hydroxyphthalimides (NHPIs) have been tested as mediators in the laccase-promoted oxidation of non-phenolic monomeric and dimeric lignin model compounds and in the delignification of kraft pulp samples. In the oxidation of the model compounds a significant increase in the product yields was observed upon increasing the electron donating properties of the NHPI ring substituent. Product yields also increased, but to a smaller extent, by increasing the electron donating properties of the aromatic substituent in the lignin models. These results suggest the contribution to the overall reactivity of both the oxidation of the aryl substituted NHPI to the N-oxyl radical (X-PINO) by laccase and the hydrogen atom transfer step from the substrate to the X-PINO, with a major contribution of the former process. When applied to the delignification of kraft pulps again the mediation efficiency increased by increasing the electron donating properties of the NHPI aryl substituent, the best mediators being 4-Me-NHPI and 4-MeO-NHPI. Thus, the use of non-phenolic lignin model compounds in the oxidation promoted by the laccase/X-NHPI system is well suited to mimic the behavior of the lignin polymer.

Journal of Molecular Catalysis B: Enzymatic published new progress about 183303-74-4. 183303-74-4 belongs to ethers-buliding-blocks, auxiliary class Benzene,Alcohol,Ether, name is 1-(3,4-Dimethoxyphenyl)-2-phenoxyethanol, and the molecular formula is C16H18O4, Product Details of C16H18O4.

Referemce:
https://en.wikipedia.org/wiki/Ether,
Ether | (C2H5)2O – PubChem

Leitch, Leonard C. published the artcileSynthesis of sulfanilylthiourea and related compounds, Safety of Formamidine disulfide dihydrochloride, the publication is Canadian Journal of Research, Section B: Chemical Sciences (1945), 139-57, database is CAplus.

Sulfanilylthiourea (I) was prepared for investigation of its chemotherapeutic properties (1) by reaction of acetylsulfanilylcyanamide (II) with H₂S or (NH₄)₂S (III) followed by deacetylation, and (2) from III and sulfanilylcyanamide (IV). A review of previous preparations of I is given. To a solution of Ca cyanamide (V) (220 g.) in H₂O (1300 mL.), stirred 3 h. at room temperature, was added p-AcNHC₆H₄SO₂Cl (VI) (200 g.) in portions for over 50 min. at 25-30°. After stirring 2 h. longer, the solution was brought to a boil, filtered, and CaCl₂.2H₂O (220 g.) dissolved in the filtrate. On cooling and standing 79% (176 g.) of Ca acetylsulfanilylcyanamide (VII) was obtained. Deacetylation of VII gave 90% of IV, m. 292-5° (decomposition). VII heated to 100° with 6 N HCl, cooled, and neutralized with NH₄OH gave sulfanilylurea (VIII) as a gum which on purification gave VIII hydrate (IX), m. 121-4°; VIII, obtained by heating IX at 100°, m. 143-7°. VII (13 g.) heated 15 h. at 95-100° with 20% III solution (33 mL.) gave 70.5% crude acetylsulfanilylthiourea (X) which after purification m. 197.5-8° (decomposition). At 160° III and VII gave acetylsulfanilamide. X (0.1 mol) added to NaOH (0.1 mol) in H₂O (200 mL.), warmed until solution was complete, decolorized, and treated with NaCl (30 g.), gave Na acetylsulfanilylthiourea (XI), m. 234.5-5°. XI (0.1 mol), 1,2-dichloroethyl acetate (0.1 mol), NaOAc.3H₂O (0.12 mol), and H₂O (100 mL.) heated to 90° for 1 h. and cooled gave 79% of acetylsulfathiazole (XII), m. 258-60°. Deacetylation of XII with NaOH gave 74.5% of sulfathiazole, m. 198-200°. IV (0.101 mol) and 20% III solution (50 mL.) heated 1 h. at 160°, cooled, and adjusted to pH 3.5 gave 89.5% of I, m. 171.5-2° (decomposition). Deacetylation of X to I was effected with 10% NaOH or 7% HCl. VII reacted with aniline gave 1-(N⁴-acetylsulfanilyl)-3-phenylguanidine, m. 221-4° (from HOAc), which on deacetylation gave 1-sulfanilyl-3-phenylguanidine; m. 206-7° (from 75% EtOH). VII with p-nitroaniline gave 1-(N⁴-acetylsulfanilyl)-3-(4-nitrophenyl)guanidine (XIII), m. 254-5°, which on deacetylation gave 1-sulfanilyl-3-(4-nitrophenyl)guanidine, m. 235-6°. XIII reduced with Fe powder and dilute HOAc and deacetylated gave 1-sulfanilyl-3-(4-aminophenyl)guanidine, m. 200-1°. Anthranilic acid and VII gave 1-(N⁴-acetylsulfanilyl)-3-(2-carboxyphenyl)guanidine (XIV), m. 286-8°, which on deacetylation gave 1-sulfanilyl-3-(2-carboxyphenyl)guanidine, m. 265-6°. XIV Na salt m. above 300°. VII, reacted with NH₄Cl at 154° for 4 h., gave acetylsulfaguanidine (XV), m. 260-2°. XV and sulfaguanidine (XVI) (from the deacetylation of XV) form a crystalline product, probably a mol. complex, m. 98-150°. XVI, m. 187°, was also prepared from IV and concentrated NH₄OH at 165°. To thiourea (0.125 mol) in Me₂CO (200 mL.) was added VI (0.124 mol) after which the mixture was stirred under reflux for 1 h. Filtration gave solid dithiodiformamidine-2HCl, m. 173-5°, while from the filtrate p-acetamidophenyl p-acetamidobenzenethiosulfonate (AcNHC₆H₄SO₂SC₆H₄NHAc) (XVII), m. 225-7° (decomposition), crystallized Deacetylation of XVII with 20% EtOH-HCl gave p-aminophenyl p-aminobenzenethiosulfonate-HCl, m. 176-9° (decomposition). 2-Methyl-2-thiopseudourea coupled with VI gave 76% of 3-(N⁴-acetylsulfanilyl)-2-methyl-2-thiopseudourea (XVIII), m. 234-5°. XVIII heated with dilute HCl, was deacetylated to 3-sulfanilyl-2-methyl-2-thiopseudourea, m. 182-4°. 2-Benzyl-2-thiopseudourea-HCl, reacted with VI gave 96.5% of 3-(N⁴-acetylsulfanilyl)-2-benzyl-2-thiopseudourea, m. 168-9°, which was deacetylated with EtOH-HCl to 3-sulfanilyl-2-benzyl-2-thiopseudourea, m. 144.5-5.5°. Thiourea (0.25 mol) refluxed 30 min. in ethanol (150 mL.) with ethylene bromide (0.25 mol) gave 72.3% of 1,2-bis(2-thiopseudourea hydrobromide) ethane (XIX), m. 238-40°, instead of the expected 2-(2-bromoethyl)-2-thiopseudourea hydrobromide. XIX reacted with VI gave 3-(N⁴-acetylsulfanilyl)-2-(2-hydroxyethyl)-2-thiopseudourea, m. 236-8°, which was deacetylated with EtOH-HCl to 3-sulfanilyl-2-(2-hydroxyethyl)-2-thiopseudourea, m. 171-3°. Acyl pseudothioureas coupled with VI gave only XVII.

Canadian Journal of Research, Section B: Chemical Sciences published new progress about 14807-75-1. 14807-75-1 belongs to ethers-buliding-blocks, auxiliary class Salt,Thiourea,Amine,Aliphatic hydrocarbon chain, name is Formamidine disulfide dihydrochloride, and the molecular formula is C2H8Cl2N4S2, Safety of Formamidine disulfide dihydrochloride.

Referemce:
https://en.wikipedia.org/wiki/Ether,
Ether | (C2H5)2O – PubChem