1-(4-乙氧基-3-甲氧基苯基)-2-(2-甲氧基苯氧基)丙烷-1,3-二醇 | 73851-59-9

• 分子结构分类: 有机化合物 - 木脂素、新木脂素和相关化合物
• 中文名称: 1-(4-乙氧基-3-甲氧基苯基)-2-(2-甲氧基苯氧基)丙烷-1,3-二醇
• 英文名称: 1-(4-ethoxy-3-methoxyphenyl)-2-(2-methoxyphenoxy)propane-1,3-diol
• CAS: 73851-59-9
• 化学式: C₁₉H₂₄O₆
• 分子量: 348.396
• InChiKey: XECRFDWEJGOIRU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  25
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  77.4
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  1-(4-乙氧基-3-甲氧基苯基)-2-(2-甲氧基苯氧基)丙烷-1,3-二醇 在 2,6-二甲基吡啶 、 lithium perchlorate 、 1-羟基苯并三唑 作用下， 以 水 、 乙腈 为溶剂， 以14.1%的产率得到1-(4-ethoxy-3-methoxyphenyl)-3-hydroxy-2-(2-methoxyphenoxy)-1-propanone
  参考文献：
  名称：

  Comparison of a series of laccase mediators in the electro-oxidation reactions of non-phenolic lignin model compounds

  摘要：

  The electro-oxidations of non-phenolic lignin model compounds in an electrolytic mediator system (EMS) have been investigated with several laccase mediators, including N-hydroxyphthalimide (NHPI), 1-hydroxybenzotriazole (HBT), violuric acid (VLA), 2,2,6,6-tetramethylpiperidine-N-oxyl (TEMPO), and 2,2'-azinobis-(3-ethylbenzothiazoline-6-sulfonate) (ABTS), under the same reaction conditions. In the bulk electrolyses of the monomeric model compound [1-(4'-ethoxy-3'-methoxyphenyl)ethanol (1G)], oxidation with NHPI gave the corresponding C-alpha=O product (2G) in high yield, whereas the oxidations with HBT, VLA, and TEMPO afforded 2G in moderate yields. The highest reaction selectivity for the guaiacyl-units was found in the oxidation conducted in the presence of ABTS, although the yield was low. In the bulk electrolyses of the dimeric model compound [4-ethoxy-3-methoxyphenylglycerol-beta-guaiacyl ether (3G)], the oxidation with NHPI gave the corresponding C-alpha=O product (4G) in high yield, whereas the oxidations with HBT, VLA, and TEMPO gave 4G in low yields. In contrast, the oxidation with ABTS gave a C-alpha-C-beta, cleavage product (5G) in 5.5% yield. The selectivity of the mediators in the EMS reaction effectively reflected the mechanisms of their reactions, as reported for the laccase mediator system. NHPI was confirmed to be the best mediator in the present system for the selective C-alpha-carbonylation of the non-phenolic beta-O-4 structures in lignin. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.electacta.2013.05.112
• 作为产物：
  描述：

  1-(4-ethoxy-3-methoxyphenyl)-3-hydroxy-2-(2-methoxyphenoxy)-1-propanone 、 硼氢化钠 生成 1-(4-乙氧基-3-甲氧基苯基)-2-(2-甲氧基苯氧基)丙烷-1,3-二醇
  参考文献：
  名称：

  FENN, P.;KIRK, T. K., J. WOOD CHEM. AND TECHNOL., 1984, 4, N 2, 131-148

  摘要：

  DOI：

文献信息

• [EN] SELECTIVE CARBON-CARBON BOND CLEAVAGE BY EARTH ABUNDANT VANADIUM COMPOUNDS UNDER VISIBLE LIGHT PHOTOCATALYSIS<br/>[FR] CLIVAGE SÉLECTIF DES LIAISONS CARBONE-CARBONE PAR DES COMPOSÉS DE VANADIUM ABONDANTS SUR TERRE SOUS L'EFFET D'UNE PHOTOCATALYSE ACTIVÉE PAR UNE LUMIÈRE VISIBLE
  申请人：UNIV NANYANG TECH

  公开号：WO2016126207A1

  公开（公告）日：2016-08-11

  Provided herein a vanadium(V) complex of formula I, where R1 to R8 are as defined herein. Also provided herein are reactions making use of the vanadium(V) complex of formula I, such as selective sp3-sp3 carbon-carbon bond cleavage under visible light photocatalysis and photodegradation of lignin.

  本文提供了一种符号为I的钒(V)配合物，其中R1至R8如本文所定义。本文还提供了利用符号为I的钒(V)配合物进行的反应，例如在可见光光催化下选择性sp3-sp3碳-碳键裂解和木质素的光降解。
• Ruthenium-Catalyzed CC Bond Cleavage in Lignin Model Substrates
  作者：Thorsten vom Stein、Tim den Hartog、Julien Buendia、Spas Stoychev、Jakob Mottweiler、Carsten Bolm、Jürgen Klankermayer、Walter Leitner

  DOI：10.1002/anie.201410620

  日期：2015.5.11

  Ruthenium–triphos complexes exhibited unprecedented catalytic activity and selectivity in the redox‐neutral CC bond cleavage of the β‐O‐4 lignin linkage of 1,3‐dilignol model compounds. A mechanistic pathway involving a dehydrogenation‐initiated retro‐aldol reaction for the CC bond cleavage was proposed in line with experimental data and DFT calculations.

  钌-三膦络合物氧化还原中性Ç表现出前所未有的催化活性和选择性的β-O-4木质素1,3- dilignol模型化合物键的C键断裂。根据实验数据和DFT计算，提出了一种涉及脱氢引发的逆式羟醛反应进行CC键断裂的机理。
• Alkoxyl- and carbon-centered radicals as primary agents for degrading non-phenolic lignin-substructure model compounds
  作者：Yasunori Ohashi、Yukiko Uno、Rudianto Amirta、Takahito Watanabe、Yoichi Honda、Takashi Watanabe

  DOI：10.1039/c0ob00797h

  日期：——

  the non-phenolic lignin model compounds and radicals produced from azo compounds in air have previously been analysed, and peroxyl radical (PR) is postulated to be responsible for lignin degradation (Kapich et al., FEBS Lett., 1999, 461, 115–119). However, because the thermolysis of azo compounds in air generates both a carbon-centred radical (CR) and a peroxyl radical (PR), we re-examined the reactivity

  木质素降解白腐菌进行经由通过氧化酶和代谢物催化的自由基反应。被称为选择性白腐真菌的担子菌可降解酚醛和非酚醛木质素亚结构，而不会使细胞外酶渗入细胞壁。已经提出了细胞外脂质过氧化作为一种​​可能的木质素分解机理，并且已经讨论了降解难降解的非酚类木质素亚结构的自由基种类。非酚类木质素模型化合物和从在空气中的偶氮化合物产生的自由基之间的反应之前已经分析，过氧化氢自由基（PR）被假定为负责木质素降解（Kapich等人，FEBS快报。，1999，461（115-119）。但是，由于偶氮化合物在空气中的热分解会同时生成碳中心自由基（CR）和过氧自由基（PR），因此我们重新检查了三个自由基烷氧基（AR），CR和PR对非自由基的反应性。酚类单体和二聚体木质素模型化合物。二聚体木质素模型化合物可通过以下反应产生的CR降解：2,2'-偶氮二（2-ami基丙烷）二盐酸盐（AAPH），它在N 2气氛下切割α-β键1
• The Immobilized Porphyrin‐Mediator System Mn(TMePyP)/clay/HBT (clay‐PMS): A Lignin Peroxidase Biomimetic Catalyst in the Oxidation of Lignin and Lignin Model Compounds
  作者：Claudia Crestini、Alessandra Pastorini、Pietro Tagliatesta

  DOI：10.1002/ejic.200400351

  日期：2004.11

  A biomimetic system for lignin peroxidase (LiP) was designed by using a cationic porphyrin, [Mn(TMePyP)OAc5], supported on the smectitic clay montmorillonite [Mn(TMePyP)/clay]. The natural role of the polypeptidic pocket of LiP was mimicked by the clay. The possibility to use low-molecular-weight redox mediators as active readily diffusible oxidizing species has been investigated. This assembly — a

  木质素过氧化物酶 (LiP) 的仿生系统是通过使用阳离子卟啉 [Mn(TMePyP)OAc5] 设计的，负载在蒙脱石粘土 [Mn(TMePyP)/粘土] 上。粘土模仿了 LiP 多肽袋的自然作用。已经研究了使用低分子量氧化还原介质作为活性易于扩散的氧化物质的可能性。这种组装——一种“合成酶”——可以定义为固定化的卟啉介体系统 (clay-PMS)。粘土-PMS 是
• Methyltrioxorhenium: a new catalyst for the activation of hydrogen peroxide to the oxidation of lignin and lignin model compounds
  作者：Claudia Crestini、Paola Pro、Veronica Neri、Raffaele Saladino

  DOI：10.1016/j.bmc.2005.01.049

  日期：2005.4

  The oxidative degradation of lignin under totally chlorine free conditions is one of the most relevant targets for the design of environmental friendly pulping and bleaching industrial processes. Methyltrioxorhenium was found a powerful and promising catalyst for the oxidation of both phenolic and non-phenolic lignin model compounds by use of hydrogen peroxide as primary oxidant. Three different technical lignins, hydrolytic sugar cane lignin (SCL), red spruce kraft lignin (RSL) and a hardwood organo-solvent lignin (OSL), that are representative examples of widely diffused para-hydroxyphenyl-guaiacyl, guaiacyl and guaiacyl-syringyl lignins, were also extensively degraded under similar experimental conditions. (c) 2005 Elsevier Ltd. All rights reserved.