Tag: M.W=250-300

Gaucher-Wieczorek, Florence S. published the artcileFluorous Tagged N-Hydroxy Phthalimide for the Parallel Synthesis of O-Aryloxyamines, Name: (3-((2-Chlorobenzyl)oxy)phenyl)boronic acid, the publication is Journal of Combinatorial Chemistry (2010), 12(5), 655-658, database is CAplus and MEDLINE.

The parallel synthesis of O-aryloxyamines remains an unfulfilled need in the field of medicinal chem. and fragment-based approaches. To fill this gap a solution-phase two-step process based on (1) a copper-catalyzed cross-coupling of aryl boronic acids with a fluorous tagged N-hydroxyphthalimide, and (2) a supported aminolysis was designed and optimized using Taguchi’s method. A library of O-aryloxyamines was synthesized in high yields with high purity and diversity.

Journal of Combinatorial Chemistry published new progress about 845551-45-3. 845551-45-3 belongs to ethers-buliding-blocks, auxiliary class Chloride,Boronic acid and ester,Benzene,Ether,Boronic Acids,Boronic Acids,Boronic acid and ester,, name is (3-((2-Chlorobenzyl)oxy)phenyl)boronic acid, and the molecular formula is C13H12BClO3, Name: (3-((2-Chlorobenzyl)oxy)phenyl)boronic acid.

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

Tan, Hua published the artcileFacile preparation of N-doped graphitic carbon encapsulated nickel catalysts for transfer hydrogenolysis of lignin β-O-4 model compounds to aromatics, SDS of cas: 183303-74-4, the publication is Sustainable Energy & Fuels (2022), 6(11), 2745-2754, database is CAplus.

Herein, N-doped carbon embedded Ni catalysts were prepared by a co-impregnation method followed by pyrolysis in a N₂ atmosphere for transfer hydrogenolysis of lignin β-O-4 alc. and ketone model compounds using isopropanol as the hydrogen source. It was found that pyrolysis at 800°C resulted in the formation of graphitic N-doped carbon shell encapsulated Ni nanoparticles (Ni@NC-800). The obtained Ni@NC-800 exhibited higher activity and selectivity to aromatics in the conversion of 2-phenoxy-1-phenylthanol and 2-phenoxyacetophenone, compared with Ni@NC-600 and Ni/NC-800. Moreover, the selectivity to aromatics could be further improved over Ni@NC-800-H, which is Ni@NC-800 after strong acid leaching. However, the presence of C_α-OH in lignin β-O-4 model compounds was essential for their product distributions. The control and characterization experiments suggested that the catalytic reaction occurred on the surface of N-doped carbon shells, because the encapsulated Ni NPs could donate electrons to the outer shells, leading to surface electron enrichment, thus making inert shells the new active sites in Ni@NC-800-H. In addition, Ni@NC-800-H was efficient for the conversion of various lignin β-O-4 alc. and ketone model compounds with methoxyl groups with high yields of the aromatic products and also possessed high stability during consecutive reaction runs, which is because Ni nanoparticles are phys. isolated from the reactive environment.

Sustainable Energy & Fuels 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 C12H14IN, SDS of cas: 183303-74-4.

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

Jia, Le published the artcileCleavage/cross-coupling strategy for converting β-O-4 linkage lignin model compounds into high valued benzyl amines via dual C-O bond cleavage, COA of Formula: C16H18O4, the publication is Chinese Chemical Letters (2022), 33(3), 1519-1523, database is CAplus.

Lignin is the most recalcitrant of the three components of lignocellulosic biomass. The strength and stability of the linkages have long been a great challenge for the degradation and valorization of lignin biomass to obtain bio-fuels and com. chems. Up to now, the selective cleavage of C-O linkages of lignin to afford chems. contains only C, H and O atoms. Authors’ group has developed a cleavage/cross-coupling strategy for converting 4-O-5 linkage lignin model compounds into high value-added compounds Herein, a palladium-catalyzed cleavage/cross-coupling of the β-O-4 lignin model compounds with amines via dual C-O bond cleavage for the preparation of benzyl amine compounds and phenols is presented.

Chinese Chemical Letters 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, COA of Formula: C16H18O4.

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

Zhang, Chaofeng published the artcilePromoting Lignin Depolymerization and Restraining the Condensation via an Oxidation-Hydrogenation Strategy, HPLC of Formula: 183303-74-4, the publication is ACS Catalysis (2017), 7(5), 3419-3429, database is CAplus.

For lignin valorization, simultaneously achieving the efficient cleavage of ether bonds and restraining the condensation of the formed fragments represents a challenge thus far. Herein, we report a two-step oxidation-hydrogenation strategy to achieve this goal. In the oxidation step, the O₂/NaNO₂/DDQ/NHPI system selectively oxidizes C_αH-OH to C_α=O within the β-O-4 structure. In the subsequent hydrogenation step, the α-O-4 and the preoxidized β-O-4 structures are further hydrogenated over a NiMo sulfide catalyst, leading to the cleavage of C_β-OPh and C_α-OPh bonds. Besides the transformation of lignin model compounds, the yield of phenolic monomers from birch wood is up to 32% by using this two-step strategy. The preoxidation of C_αH-OH to C_α=O not only weakens the C_β-OPh ether bond but also avoids the condensation reactions caused by the presence of C_α⁺ from dehydroxylation of C_αH-OH. Furthermore, the NiMo sulfide prefers to catalyze the hydrogenative cleavage of the C_β-OPh bond connecting with a C_α=O rather than catalyze the hydrogenation of C_α=O back to the original C_αH-OH, which further ensures and utilizes the advantages of preoxidation

ACS Catalysis 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 C10H9NO, HPLC of Formula: 183303-74-4.

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

D’Alfonso, Claudio published the artcileComparing the catalytic efficiency of ring substituted 1-hydroxybenzotriazoles as laccase mediators, Formula: C16H18O4, the publication is Tetrahedron (2014), 70(18), 3049-3055, database is CAplus.

A series of ring substituted 1-hydroxybenzotriazoles (6-X-HBTs) have been tested as mediators in the laccase-promoted oxidation of 4-methoxybenzyl alc., 3,4-dimethoxybenzyl alc., and the dimeric lignin model 1-(3,4-dimethoxyphenyl)-2-phenoxyethanol. The effect of the aryl substituents on the yields of oxidation products is remarkable. The catalytic mediation efficiency increases as the electron releasing (ER) properties of the substituent increases up to a maximum value for 6-CH₃-HBT, which resulted a very efficient mediator. Both the oxidation of the 6-X-HBTs to the N-oxyl radicals (6-X-BTNO) by laccase and the hydrogen atom transfer (HAT) process from the benzylic C-H to the 6-X-BTNO contribute to the overall reactivity. The former process is favored by ER substituents that lower the mediator redox potentials. On the other hand, ER substituents decrease the 6-X-BTNO reactivity in the HAT process due to a decrease in the NO-H BDE value, as assessed in this study through a radical equilibration technique.

Tetrahedron 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, Formula: C16H18O4.

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

Kalcic, Filip published the artcilePolysubstituted Pyrimidines as mPGES-1 Inhibitors: Discovery of Potent Inhibitors of PGE₂ Production with Strong Anti-inflammatory Effects in Carrageenan-Induced Rat Paw Edema, SDS of cas: 849062-21-1, the publication is ChemMedChem (2020), 15(15), 1398-1407, database is CAplus and MEDLINE.

We report an extensive structure-activity relationship optimization of polysubstituted pyrimidines that led to the discovery of 5-butyl-4-(4-benzyloxyphenyl)-6-phenylpyrimidin-2-amine, and its difluorinated analog. These compounds are sub-micromolar inhibitors of PGE₂ production (IC₅₀ as low as 12 nM). In order to identify the mol. target of anti-inflammatory pyrimidines, we performed extensive studies including enzymic assays, homol. modeling and docking. The difluorinated analog simultaneously inhibits two key enzymes of the arachidonic acid cascade, namely mPGES-1 and COX-2, with mPGES-1 inhibition being the principal mechanism of action. Other pyrimidines studied are potent mPGES-1 inhibitors with no observed inhibition of COX-1/2 enzymes. Moreover, the two most potent compounds proved to be significantly effective in vivo in a model of acute inflammation, suppressing carrageenan-induced rat paw edema by 36 and 46%. The promising results of this study warrant further preclin. evaluation of selected anti-inflammatory candidates.

ChemMedChem published new progress about 849062-21-1. 849062-21-1 belongs to ethers-buliding-blocks, auxiliary class Chloride,Boronic acid and ester,Benzene,Ether,Boronic Acids,Boronic Acids,Boronic acid and ester,, name is (4-((3-Chlorobenzyl)oxy)-3,5-dimethylphenyl)boronic acid, and the molecular formula is C15H16BClO3, SDS of cas: 849062-21-1.

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

Oster, Alexander published the artcileBicyclic Substituted Hydroxyphenylmethanone Type Inhibitors of 17 β-Hydroxysteroid Dehydrogenase Type 1 (17 β-HSD1): The Role of the Bicyclic Moiety, Related Products of ethers-buliding-blocks, the publication is ChemMedChem (2011), 6(3), 476-487, database is CAplus and MEDLINE.

An attractive target that has still to be explored for the treatment of estrogen-dependent diseases, such as breast cancer and endometriosis, is the enzyme responsible for the last step in the biosynthesis of estradiol (E2): 17β-hydroxysteroid dehydrogenase type 1 (17β-HSD1). It catalyzes the reduction of the weakly active estrone (E1) into E2, which is the most potent estrogen in humans. Inhibition of 17β-HSD1 lowers intracellular E2 concentrations and thus presents a therapeutic target for estrogen-dependent pathologies. Recently, we reported a new class of highly active and selective 17β-HSD1 inhibitors: bicyclic substituted hydroxyphenylmethanones. Here, further structural variations on the bicyclic moiety are described, especially focusing on the exchange of its hydroxy function. Twenty-nine novel inhibitors were synthesized and evaluated for 17β-HSD1 inhibition in a cell-free and cellular assay, for selectivity toward 17βHSD2 and estrogen receptors (ER) alpha and beta, as well as for metabolic stability. The best compound (I) exhibited IC₅₀ values of 12 nM (cell-free assay) and 78 nM (cellular assay), high selectivity for 17β-HSD1, and reasonable metabolic stability. A mol. docking study provided insight into the protein-ligand interactions of this compound with 17β-HSD1.

ChemMedChem published new progress about 845551-45-3. 845551-45-3 belongs to ethers-buliding-blocks, auxiliary class Chloride,Boronic acid and ester,Benzene,Ether,Boronic Acids,Boronic Acids,Boronic acid and ester,, name is (3-((2-Chlorobenzyl)oxy)phenyl)boronic acid, and the molecular formula is C13H12BClO3, Related Products of ethers-buliding-blocks.

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

Zheng, Ming published the artcileVisible-light-induced C-C bond cleavage of lignin model compounds with cyanobenziodoxolone, SDS of cas: 183303-74-4, the publication is Tetrahedron Letters (2020), 61(42), 152420, database is CAplus.

The catalytic degradation of lignin to value-added chems. has received considerable attention over the past decade. Photocatalysis provides promising approaches to enable previously inaccessible transformations. However, examples of the visible-light promoted degradation of lignin are still limited. In this work, the visible-light-induced selective C-C bond cleavage of β-O-4 lignin model compounds was disclosed via β-scission of in situ generated alkoxy radical intermediates. With cyanobenziodoxolone as the oxidant, a variety of substrates could be transformed into aldehydes in moderate to good yields. In addition, unexpected acetal esters which could conveniently furnish formaldehyde and phenols by alcoholysis were observed

Tetrahedron Letters 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 C7H4ClIO2, SDS of cas: 183303-74-4.

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

Wang, Yinling published the artcileCeCl₃-promoted simultaneous photocatalytic cleavage and amination of Cα-Cβ bond in lignin model compounds and native lignin, SDS of cas: 183303-74-4, the publication is CCS Chemistry (2020), 2(3), 107-117, database is CAplus.

It remains challenging to achieve valuable platform chems. from lignin because of its complicated polymeric structure and inherent inert chem. activities. So far, only a few examples have been reported for the selective cleavage of C-C bonds in lignin due to their intrinsic inertness and ubiquity. Here, we present a simple and com. available cerium(III) chloride (CeCl₃)-promoted photocatalytic depolymerization strategy to realize the simultaneous cleavage and amination of Cα-Cβ bond in a variety of lignin model compounds at room temperature This procedure does not require any pretreatments and breakdown of C-O bonds or loss of γ-CH₂OH group to generate aldehydes (up to 97%) and N-containing products (up to 95%) in good to excellent yields. Addnl., this CeCl₃-based photocatalyst system could maintain excellent catalytic performance even after 10 sequential cycles with new starting materials. Moreover, this approach realizes the precise control over the reaction via switching the external light stimuli on/off. Further, this method is effective for the depolymerization of real lignin, thus affording the corresponding cleavage and amination products of Cα-Cβ bonds.

CCS Chemistry 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 C2H4ClNO, SDS of cas: 183303-74-4.

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

Dawange, Monali published the artcileSelective Aerobic Benzylic Alcohol Oxidation of Lignin Model Compounds: Route to Aryl Ketones, Safety of 1-(3,4-Dimethoxyphenyl)-2-phenoxyethanol, the publication is ChemCatChem (2015), 7(3), 401-404, database is CAplus.

A mild and chemoselective oxidation of the α-alc. in β-O-4′-ethanoaryl and β-O-4′-glycerolaryl ethers, I [R³ = R⁴ = R³‘ = R⁵‘ = H OMe; R³ = R³‘ = R⁵‘ = H, R⁴ = OMe; R³ = R⁴ = R⁵‘ = H, R³‘ = OMe; R³ = R⁵‘ = H, R⁴ = R³‘ = OMe; R³ = R⁴ = OMe, R³‘ = H, OMe, R⁵‘ = H; R³ = R³‘ = OMe, R⁴ = OH, R⁵‘ = H] and II [ R³ = R⁴ = R³‘ = OMe, H; R³ = H, R⁴ = R³‘ = OMe; R³ = R³‘ = OMe, R⁴ = OH] , resp., has been developed. The benzylic alcs. were selectively dehydrogenated to the corresponding ketones in 60-93 % yield. A one-pot selective route to aryl Et ketones was performed. The catalytic system comprises recyclable heterogeneous palladium, mild reaction conditions, green solvents, and oxygen in air as oxidant. Catalytic amounts of a coordinating polyol were found pivotal for an efficient aerobic oxidation

ChemCatChem 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, Safety of 1-(3,4-Dimethoxyphenyl)-2-phenoxyethanol.

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