2628-17-3Relevant articles and documents
Synthesis method of hydroxyl-substituted styrene compound and synthesis method of photoresist resin monomer
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Paragraph 0006; 0083-0085, (2022/01/12)
The present invention provides a synthesis method of a hydroxyl-substituted styrene compound and a synthesis method of photoresist resin monomer. The synthesis method of the hydroxyl-substituted styrene compound comprises the following steps: a) the compound of formula I-1 is reacted with the Wetting reagent to obtain a compound of formula I-2. The synthesis method of the photoresist resin monomer comprises the following steps: a) the synthesis method of the styrene compound substituted with the above hydroxyl group to obtain a compound of formula I-2; b) the compound of formula I-2 is reacted with an acylating reagent to obtain the photoresist resin monomer, the structural formula is referred to formula I-3. The synthesis method of hydroxyl-substituted styrene compounds and photoresist resin monomers of the present invention has high yield and high purity.
Two-photon induced isomerization through a cyaninic molecular antenna in azo compounds
Villatoro, Emmanuel,Mu?oz-Rugeles, Leonardo,Durán-Hernández, Jesús,Salcido-Santacruz, Bernardo,Esturau-Escofet, Nuria,López-Cortés, Jose G.,Ortega-Alfaro, M. Carmen,Peón, Jorge
supporting information, p. 3123 - 3126 (2021/04/02)
We present a new design for non-linear optically responsive molecules based on a modular scheme where a polymethinic antenna section with important two-photon absorption properties is bonded to an isomerizable actuator section composed of a stilbenyl-azopyrrole unit. Upon two photon excitation, energy migration from the antenna-localized second singlet excited state to the stilbenyl-azopyrrole section allows for efficient indirect excitation and phototransformation of this actuator.
Cross-Coupling Reactions with 2-Amino-/Acetylamino-Substituted 3-Iodo-1,4-naphthoquinones: Convenient Synthesis of Novel Alkenyl- And Alkynylnaphthoquinones and Derivatives
Demidoff, Felipe C.,Rodrigues Filho, Eduardo José P.,De Souza, Andréa Luzia F.,Netto, Chaquip D.,De Carvalho, Leandro L.
supporting information, p. 4097 - 4109 (2021/08/31)
Functionalized 1,4-naphthoquinones have been employed as versatile synthons in organic synthesis, in addition to presenting a large array of biological activities. Herein, the applications of 2-amino-/ acetylamino-substituted 3-iodo-1,4-naphthoquinones in cross-coupling reactions are described to successfully afford sixteen novel 3-styryl-1,4-naphthoquinones (amino-stilbene-quinone hybrids) and four 3-alkynyl-1,4-naphthoquinone in overall good yields. Interestingly, the alkynylated derivatives could be obtained from ligand- and Pd-free Cu I -mediated cross-coupling reactions, after extensive investigations to exclude Pd as a co-catalyst. Lastly, the desilanized terminal alkyne was subjected to click chemistry reactions to give two novel triazole-1,4-naphthoquinone hybrids.
Direct α-Acylation of Alkenes via N-Heterocyclic Carbene, Sulfinate, and Photoredox Cooperative Triple Catalysis
Liu, Kun,Studer, Armido
supporting information, p. 4903 - 4909 (2021/05/04)
N-Heterocyclic carbene (NHC) catalysis has emerged as a versatile tool in modern synthetic chemistry. Further increasing the complexity, several processes have been introduced that proceed via dual catalysis, where the NHC organocatalyst operates in concert with a second catalytic moiety, significantly enlarging the reaction scope. In biological transformations, multiple catalysis is generally used to access complex natural products. Guided by that strategy, triple catalysis has been studied recently, where three different catalytic modes are merged in a single process. In this Communication, direct α-C-H acylation of various alkenes with aroyl fluorides using NHC, sulfinate, and photoredox cooperative triple catalysis is reported. The method allows the preparation of α-substituted vinyl ketones in moderate to high yields with excellent functional group tolerance. Mechanistic studies reveal that these cascades proceed through a sequential radical addition/coupling/elimination process. In contrast to known triple catalysis processes that operate via two sets of interwoven catalysis cycles, in the introduced process, all three cycles are interwoven.
Rapid biosynthesis of phenolic glycosides and their derivatives from biomass-derived hydroxycinnamates
Zhao, Mingtao,Hong, Xulin,Abdullah,Yao, Ruilian,Xiao, Yi
, p. 838 - 847 (2021/02/09)
Biomass-derived hydroxycinnamates (mainly includingp-coumaric acid and ferulic acid), which are natural sources of aromatic compounds, are highly underutilized resources. There is a need to upgrade them to make them economically feasible. Value-added phenolic glycosides and their derivatives, both belonging to a class of plant aromatic natural products, are widely used in the nutraceutical, pharmaceutical, and cosmetic industries. However, their complex aromatic structures make their efficient biosynthesis a challenging process. To overcome this issue, we created three novel synthetic cascades for the biosynthesis of phenolic glycosides (gastrodin, arbutin, and salidroside) and their derivatives (hydroquinone, tyrosol, hydroxytyrosol, and homovanillyl alcohol) fromp-coumaric acid and ferulic acid. Moreover, because the biomass-derived hydroxycinnamates directly provided aromatic units, the cascades enabled efficient biosynthesis. We achieved substantially high production rates (up to or above 100-fold enhancement) relative to the glucose-based biosynthesis. Given the ubiquity of the aromatic structure in natural products, the use of biomass-derived aromatics should facilitate the rapid biosynthesis of numerous aromatic natural products.
Rapid synthesis method of biomass-based olefin
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Paragraph 0020; 0041-0048, (2021/07/31)
The invention discloses a rapid synthesis method of biomass-based olefin, which comprises the following steps: by taking a biomass ketone compound as a substrate and 2-pentanol as a hydrogen source and a solvent at the same time, under the action of hafnium/zirconium-based catalysts such as hafnium phenylphosphonate and Zirconium phenylphosphonate, hafnium phytate andzirconium phytate and hafnium polydivinylphenylphosphonate and zirconium polydivinylphenylphosphonate, selectively converting a biomass-based ketone compound into a corresponding alcohol compound, and continuously dehydrating to prepare olefin. According to the present invention, the time required by the system reaction is substantially shortened and is at least 2 h, the target product selectivity is significantly improved, the conversion rate of the representative reaction 4 '-methoxypropiophenone can at least achieve 99.8%, and the anethole yield can achieve 98.1%.
MODIFIED MONOMER, MODIFIED POLYMER COMPRISING THE SAME AND METHOD FOR PREPARING THEM
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Paragraph 0188-0191, (2021/05/18)
A modified monomer useful for the polymer modification of formula 1. The present invention relates to a method for preparing a modified monomer, a modified polymer comprising a modified monomer-derived functional group, a rubber composition comprising the modified polymer, and a molded article produced from the rubber composition.
Copper(ii)-catalyzed protoboration of allenes in aqueous media and open air
Nekvinda, Jan,Santos, Webster L.,Snead, Russell F.
supporting information, p. 14925 - 14931 (2021/09/04)
A method has been developed for the facile Cu(ii)-catalyzed protoboration of monosubstituted allenes in aqueous media under atmospheric conditions. The reaction occurs site selectively, favoring internal alkene protoboration to afford 1,1-disubstituted vinylboronic acid derivatives (up to 93?:?7) with modest to good yields. The method has been applied to a variety of phenylallene derivatives as well as alkyl-substituted allenes. This journal is
Site-Selective Acceptorless Dehydrogenation of Aliphatics Enabled by Organophotoredox/Cobalt Dual Catalysis
Zhou, Min-Jie,Zhang, Lei,Liu, Guixia,Xu, Chen,Huang, Zheng
supporting information, p. 16470 - 16485 (2021/10/20)
The value of catalytic dehydrogenation of aliphatics (CDA) in organic synthesis has remained largely underexplored. Known homogeneous CDA systems often require the use of sacrificial hydrogen acceptors (or oxidants), precious metal catalysts, and harsh reaction conditions, thus limiting most existing methods to dehydrogenation of non- or low-functionalized alkanes. Here we describe a visible-light-driven, dual-catalyst system consisting of inexpensive organophotoredox and base-metal catalysts for room-temperature, acceptorless-CDA (Al-CDA). Initiated by photoexited 2-chloroanthraquinone, the process involves H atom transfer (HAT) of aliphatics to form alkyl radicals, which then react with cobaloxime to produce olefins and H2. This operationally simple method enables direct dehydrogenation of readily available chemical feedstocks to diversely functionalized olefins. For example, we demonstrate, for the first time, the oxidant-free desaturation of thioethers and amides to alkenyl sulfides and enamides, respectively. Moreover, the system's exceptional site selectivity and functional group tolerance are illustrated by late-stage dehydrogenation and synthesis of 14 biologically relevant molecules and pharmaceutical ingredients. Mechanistic studies have revealed a dual HAT process and provided insights into the origin of reactivity and site selectivity.
Discovery, Biocatalytic Exploration and Structural Analysis of a 4-Ethylphenol Oxidase from Gulosibacter chungangensis
Alvigini, Laura,Fraaije, Marco W.,Gran-Scheuch, Alejandro,Guo, Yiming,Mattevi, Andrea,Saifuddin, Mohammad,Trajkovic, Milos
, p. 3225 - 3233 (2021/10/04)
The vanillyl-alcohol oxidase (VAO) family is a rich source of biocatalysts for the oxidative bioconversion of phenolic compounds. Through genome mining and sequence comparisons, we found that several family members lack a generally conserved catalytic aspartate. This finding led us to study a VAO-homolog featuring a glutamate residue in place of the common aspartate. This 4-ethylphenol oxidase from Gulosibacter chungangensis (Gc4EO) shares 42 % sequence identity with VAO from Penicillium simplicissimum, contains the same 8α-N3-histidyl-bound FAD and uses oxygen as electron acceptor. However, Gc4EO features a distinct substrate scope and product specificity as it is primarily effective in the dehydrogenation of para-substituted phenols with little generation of hydroxylated products. The three-dimensional structure shows that the characteristic glutamate side chain creates a closely packed environment that may limit water accessibility and thereby protect from hydroxylation. With its high thermal stability, well defined structural properties and high expression yields, Gc4EO may become a catalyst of choice for the specific dehydrogenation of phenolic compounds bearing small substituents.
