Category: 183303-74-4

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

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

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

Collier, Willard E. published the artcileAlkaline hydrolysis of nonphenolic β-O-4 lignin model dimers. Further studies of the substituent effect on the leaving phenoxide, Recommanded Product: 1-(3,4-Dimethoxyphenyl)-2-phenoxyethanol, the publication is Holzforschung (1996), 50(5), 420-424, database is CAplus.

Reaction rates and activation parameters for the alk. hydrolysis of nonphenolic β-O-4 lignin models [2-(4-substituted-phenoxy)-1-(3,4-dimethoxyphenyl)ethanol] were compared to 2-methoxylated B-ring analogs run earlier. The Hammett plot with the best fit used σ^– values to give a ρ of 1.9 ± 0.2, while the 2-methoxyl-substituted compounds had a ρ of 2.3 ± 0.3. Compounds with a methoxyl group at the ortho position of the leaving phenoxide ion hydrolyzed slightly faster than the nonmethoxylated analogs, indicating that the 2-methoxy group is a weak electron withdrawer. The strong electron-withdrawing 4-CHO and 4-CF₃ substituents gave significantly different activation parameters than the unsubstituted compound Experiments with O-labeled water suggested that the earlier proposed S_NAr mechanism for the alk. hydrolysis of strong electron-withdrawing compounds is not correct. It appears that all nonphenolic β-O-4 dimers are hydrolyzed by a neighboring group mechanism.

Holzforschung 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, Recommanded Product: 1-(3,4-Dimethoxyphenyl)-2-phenoxyethanol.

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

Baciocchi, Enrico published the artcileLignin peroxidase-catalyzed oxidation of nonphenolic trimeric lignin model compounds: Fragmentation reactions in the intermediate radical cations, Application In Synthesis of 183303-74-4, the publication is Journal of Organic Chemistry (2003), 68(23), 9061-9069, database is CAplus and MEDLINE.

The H₂O₂-promoted oxidations of the two nonphenolic β-O-aryl lignin model trimers 1 and 2, catalyzed by lignin peroxidase (LiP) at pH = 3.5, have been studied. The results have been compared with those obtained in the oxidation of 1 and 2 with the genuine one-electron oxidant potassium 12-tungstocobalt(III)ate. These models present a different substitution pattern of the three aromatic rings, and by one-electron oxidation, they form radical cations with the pos. charge, which is localized in the dialkoxylated ring as also evidenced by a pulse radiolysis study. Both the oxidations with the enzymic and with the chem. systems lead to the formation of products deriving from the cleavage of C-C and C-H bonds in a β position with respect to the radical cation with the charge residing in the dialkoxylated ring (3,4-dimethoxybenzaldehyde (5) and a trimeric ketone 6 in the oxidation of 1 and a dimeric aldehyde 8 and a trimeric ketone 9 in the oxidation of 2). These products are accompanied by a dimeric aldehyde 7 in the oxidation of 1 and 4-methoxybenzaldehyde (10) in the oxidation of 2. The unexpected formation of these two products has been explained by suggesting that 1^â€? and 2^â€? can also undergo an intramol. electron transfer leading to the radical cations 1a^â€? and 2a^â€? with the charge residing in a monoalkoxylated ring. The fast cleavage of a C-C bond β to this ring, leading to 7 from 1^â€? and to 10 from 2^â€?, is the driving force of the endoergonic electron transfer. A kinetic steady-state investigation of the LiP-catalyzed oxidation of the trimer 2, the dimeric model 1-(3,4-dimethoxyphenyl)-2-phenoxy-1-ethanol (4), and 3,4-dimethoxybenzyl alc. (3) has indicated that the turnover number (k_cat) and the affinity for the enzyme decrease significantly by increasing the size of the model compound In contrast, the three substrates exhibited a very similar reactivity toward a chem. oxidant [Co^IIIW]. This suggests a size-dependent interaction of the enzyme with the substrate which may influence the efficiency of the electron transfer.

Journal of Organic 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 C16H18O4, Application In Synthesis of 183303-74-4.

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

Galkin, Maxim V. published the artcileMild and Robust Redox-Neutral Pd/C-Catalyzed Lignol β-O-4′ Bond Cleavage Through a Low-Energy-Barrier Pathway, Safety of 1-(3,4-Dimethoxyphenyl)-2-phenoxyethanol, the publication is ChemSusChem (2015), 8(13), 2187-2192, database is CAplus and MEDLINE.

A Pd/C catalyzed redox neutral C-O bond cleavage of 2-aryloxy-1-arylethanols has been developed. The reactions are carried out at 80 °C, in air, using a green solvent system to yield the aryl ketones in near quant. yields. Addition of catalytic amounts of a hydrogen source to the reaction mixture activates the catalyst to proceed through a low energy barrier pathway. Initial studies support a transfer hydrogenolysis reaction mechanism that proceeds through an initial dehydrogenation followed by an enol adsorption to Pd/C and a reductive C-O bond cleavage.

ChemSusChem 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

Sun, Kangkang published the artcileCobalt Nanoparticles Embedded in N-Doped Porous Carbon Derived from Bimetallic Zeolitic Imidazolate Frameworks for One-Pot Selective Oxidative Depolymerization of Lignin, Category: ethers-buliding-blocks, the publication is ChemCatChem (2019), 11(4), 1264-1271, database is CAplus.

Co nanoparticles embedded in N-doped porous C (Co@CN) were prepared by the pyrolysis of bimetallic zeolitic imidazolate frameworks (BMZIFs) based on ZIF-8 and ZIF-67. The catalyst shows excellent catalytic efficiency in 1-pot selective oxidative cleavage of different linkages like β-O-4, α-O-4 and β-1 in organosolv lignin and lignin model compounds in the presence of O (ambient pressure) under mild conditions (383 K). Compared with traditional supported catalyst, the catalyst gives a highly hollow structure, which favored the adsorption of substrates and O. The uniform Co nanoparticles surrounded by N-doped graphitic structures and the strong electron transfer from graphitic N to Co NPs make it hard to be oxidized prior to use and higher catalytic reactivity. Also, the catalyst can be easily recovered by magnetic force after the reaction, and reused after reduction for 5 times without an obvious change in yields.

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 C27H29N5O5, Category: ethers-buliding-blocks.

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

Lui, Matthew Y. published the artcileUnravelling Some of the Key Transformations in the Hydrothermal Liquefaction of Lignin, Synthetic Route of 183303-74-4, the publication is ChemSusChem (2017), 10(10), 2140-2144, database is CAplus and MEDLINE.

Using both exptl. and computational methods, focusing on intermediates and model compounds, some of the main features of the reaction mechanisms that operate during the hydrothermal processing of lignin were elucidated. Key reaction pathways and their connection to different structural features of lignin were proposed. Under neutral conditions, subcritical water was demonstrated to act as a bifunctional acid/base catalyst for the dissection of lignin structures. In a complex web of mutually dependent interactions, guaiacyl units within lignin were shown to significantly affect overall lignin reactivity.

ChemSusChem 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, Synthetic Route of 183303-74-4.

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