1-(4-hydroxy-3-methoxyphenyl)-2-(2,6-dimethoxyphenoxy)-propane-1,3-diol | 61413-50-1

• 分子结构分类: 有机化合物 - 木脂素、新木脂素和相关化合物
• 英文名称: 1-(4-hydroxy-3-methoxyphenyl)-2-(2,6-dimethoxyphenoxy)-propane-1,3-diol
• 英文别名: 2-(2,6-dimethoxyphenoxy)-1-(4-hydroxy-3-methoxyphenyl)propane-1,3-diol
• CAS: 61413-50-1
• 化学式: C₁₈H₂₂O₇
• 分子量: 350.368
• InChiKey: UZQRRMGNZTWTOB-UHFFFAOYSA-N

物化性质

• 沸点：
  581.1±50.0 °C(Predicted)
• 密度：
  1.279±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  25
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  97.6
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  1-(4-hydroxy-3-methoxyphenyl)-2-(2,6-dimethoxyphenoxy)-propane-1,3-diol 在 三甲基溴硅烷 、 碳酸氢钠 作用下， 以 氯仿 、 水 为溶剂， 反应 0.03h， 生成
  参考文献：
  名称：

  木质素生物合成研究：醌甲基化物的反应性的Diastereopreferential形成p -Hydroxyphenyl-和愈创木型β- Ø -4结构

  摘要：

  对苯醌甲基化物作为临时中间体参与木质素的生物合成，并且芳构化步骤对所得木质素的化学结构有很大影响。一系列醌甲基化物（QMS）的合成，并使其与水在pH为3-7的缓冲液，在25℃下反应到的模拟物形成的p -hydroxyphenyl-和愈创木基型（H-和G型，分别地）β -裸子植物植物细胞壁中的O -4结构。加水发生在3-甲氧基取代的QM（G型QM）中，半衰期为1.4–15分钟。相反，未取代的QM（H型QM）非常不稳定。他们被芳香化为β- O-4产品的半衰期仅为10–40 s。H型质量管理体系中的快速芳香化可以提供优于G型物质的优势，以有效地驱动木质素聚合循环，这可能有助于开发高度木质化的压缩木材。在加水反应中，β- O -4产物的苏式异构体比G型和H型QM的赤式异构体立体立体形成的比例更高（分别为24:76和50:50的赤/苏比） ）。赤字比例在较低pH条件下，异构体较高。这种依赖于pH的趋势与先前对3

  DOI：

  10.1021/acs.jafc.8b06465
• 作为产物：
  描述：

  在 sodium tetrahydroborate 、 5%-palladium/activated carbon 、 氢气 、 溴 、 potassium carbonate 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 、 水 、 乙腈 为溶剂， 反应 2.5h， 生成 1-(4-hydroxy-3-methoxyphenyl)-2-(2,6-dimethoxyphenoxy)-propane-1,3-diol
  参考文献：
  名称：

  Efficient Cobalt-Catalyzed Oxidative Conversion of Lignin Models to Benzoquinones

  摘要：

  Phenolic lignin model monomers and dimers representing the primary substructural units of lignin were successfully oxidized to benzoquinones in high yield with molecular oxygen using new Co-Schiff base catalysts bearing a bulky heterocyclic nitrogen base as a substituent. This is the first example of a catalytic system able to convert both S and G lignin model phenols in high yield, a process necessary for effective use of lignin as a chemical feedstock.

  DOI：

  10.1021/ol401065r

文献信息

• Singlet oxygen in the photodegradation of lignin models
  作者：Claudia Crestini、Maurizio D'Auria

  DOI：10.1016/s0040-4020(97)00460-2

  日期：1997.6

  of the carbonyl group is not indispensable to have the cleavage reaction. The use of the model compound 10 showed that, when the phenoxy part of the molecule shows a lower reactivity towards singlet oxygen, the oxidation of the phenol moiety to hydroquinone can occur. The photochemical behaviour of these model compounds can be rationalised from a reaction of singlet oxygen with the phenoxy part of the

  研究了单线态氧存在下木质素模型的光化学氧化。所述非酚β-O-4芳基醚衍生物的治疗6，7和8在氧和玫瑰红的存在，得到的产品从一个正式的β-CO裂解形成导出。通过这种方式，衍生物12，13，和15获得的。酚类β-O-4芳基酯9的光化学氧化得到相同类型的产物，证实在这种情况下，羰基的存在对于裂解反应不是必不可少的。模型化合物10的使用结果表明，当分子的苯氧基部分显示出对单线态氧较低的反应性时，酚部分会氧化为对苯二酚。这些模型化合物的光化学行为可以通过单线态氧与分子的苯氧基部分的反应来合理化。
• Selective Oxidation of Lignin Model Compounds
  作者：Ruili Gao、Yanding Li、Hoon Kim、Justin K. Mobley、John Ralph

  DOI：10.1002/cssc.201800598

  日期：2018.7.11

  planet's most abundant renewable source of aromatic compounds, is difficult to degrade efficiently to welldefined aromatics. We developed a microwave‐assisted catalytic Swern oxidation system using an easily prepared catalyst, MoO2Cl2(DMSO)2, and DMSO as the solvent and oxidant. It demonstrated high efficiency in transforming lignin model compounds containing the units and functional groups found in

  木质素是地球上最丰富的芳香族化合物可再生资源，很难有效地降解为定义明确的芳香族化合物。我们使用容易制备的催化剂MoO 2 Cl 2（DMSO）2开发了微波辅助的Swern氧化系统，以DMSO作溶剂和氧化剂。它证明了转化含有天然木质素中所含单元和官能团的木质素模型化合物的高效率。芳环取代基极大地影响了β-醚酚二聚体裂解生成芥子醛和松柏醛的选择性，这些单体通常不是通过氧化方法生产的。对两个关键中间体的时程研究提供了对反应途径的深入了解。由于该氧化系统的广泛范围以及有关其机理的见解，因此该策略可在一般意义上进行调整并应用于从酚醛和木质素生产有用的芳香族化学品中。
• Identification and quantification of lignin monomers and oligomers from reductive catalytic fractionation of pine wood with GC × GC – FID/MS
  作者：Hang Dao Thi、Korneel Van Aelst、Sander Van den Bosch、Rui Katahira、Gregg T. Beckham、Bert F. Sels、Kevin M. Van Geem

  DOI：10.1039/d1gc03822b

  日期：——

  lignin and to evaluate lignocellulose biorefinery processes. In this study, an in-depth characterization of lignin oil, obtained from reductive catalytic fractionation (RCF) of pine wood, was performed with quantitative GC × GC – FID analysis and qualitative GC × GC – MS. By utilizing high-temperature resistant column sets in the GC × GC system and by applying a derivatization step, unambiguous detection

  彻底的木质素表征对于了解木质素的物理化学性质和评估木质纤维素生物精炼工艺至关重要。在本研究中，通过定量 GC × GC – FID 分析和定性 GC × GC – MS 对从松木的还原催化分馏 (RCF) 中获得的木质素油进行了深入表征。通过在 GC × GC 系统中使用耐高温柱组并应用衍生化步骤，可以明确检测木质素单体、二聚体和三聚体。除了确认 11 种单体（相当于 RCF 木质素油的 34 wt%）的身份外，还通过质谱分析全面鉴定了 36 个二聚体（16 wt%）和 21 个三聚体（7 wt%）通过 FID 量化，包括另外 23 重量％的 RCF 木质素油的特性。所提出的结构揭示了二聚体和三聚体低聚物中存在的互连，包含 β-5、β-1、β-β、5-5 和少量 β-O-4 和 4-O-5 键。此外，鉴定了二聚体和三聚体分子中的脂肪族末端单元，由 C4 位置的各种取代基组成，之前在 RCF
• 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.
• Immobilized methyltrioxo rhenium (MTO)/H2O2 systems for the oxidation of lignin and lignin model compounds
  作者：Claudia Crestini、Maria Chiara Caponi、Dimitris S. Argyropoulos、Raffaele Saladino

  DOI：10.1016/j.bmc.2006.03.046

  日期：2006.8

  A convenient and efficient application of heterogeneous methylrhenium trioxide (MTO) systems for the selective oxidation of lignin model compounds and lignins is reported. Environmental friendly and low-cost H2O2 was used as the oxygen atom donor. Overall, the data presented and discussed in this paper point toward the conclusion that the immobilized heterogeneous catalytic systems based on H2O2/and MTO catalysts are able to extensively oxidize both phenolic and non-phenolic, monomeric, and dimeric, lignin model compounds. Condensed diphenylmethane models were found also extensively oxidized. Technical lignins, such as hydrolytic sugar cane lignin (SCL) and red spruce kraft lignin (RSL), displayed oxidative activity with immobilized MTO catalytic systems. After oxidation, these lignins displayed the formation of more soluble lignin fragments with a high degree of degradation as indicated by the lower contents of aliphatic and condensed OH groups, and the higher amounts of carboxylic acid moieties. Our data indicate that immobilized MTO catalytic systems are significant potential candidates for the development of alternative totally chlorine-free delignification processes and environmentally sustainable lignin selective modification reactions. (c) 2006 Elsevier Ltd. All rights reserved.