4-(1-hydroxy-2-(2-methoxyphenoxy)ethyl)-2,6-dimethoxyphenol | 18167-89-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 4-(1-hydroxy-2-(2-methoxyphenoxy)ethyl)-2,6-dimethoxyphenol
• 英文别名: Syringylglycol-β-guajacylether；1-(4-hydroxy-3,5-dimethoxyphenyl)-2-(2'-methoxyphenoxy)-1-ethanol；syringylglycol β-guaiacyl ether；4-[1-hydroxy-2-(2-methoxyphenoxy)ethyl]-2,6-dimethoxyphenol
• CAS: 18167-89-0
• 化学式: C₁₇H₂₀O₆
• 分子量: 320.342
• InChiKey: FOMBFYGXXPQPBK-UHFFFAOYSA-N

物化性质

• 沸点：
  501.6±50.0 °C(Predicted)
• 密度：
  1.235±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  23
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 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：

  4-(1-hydroxy-2-(2-methoxyphenoxy)ethyl)-2,6-dimethoxyphenol 在 氢溴酸 作用下， 以 二氯甲烷 为溶剂， 反应 0.17h， 生成 4-[1-Bromo-2-(2-methoxy-phenoxy)-ethyl]-2,6-dimethoxy-phenol
  参考文献：
  名称：

  Adducts of anthrahydroquinone and anthranol with lignin model quinone methides. 1. Synthesis and characterization

  摘要：

  DOI：

  10.1021/jo00139a020
• 作为产物：
  描述：

  3',4',5'-三甲氧基苯乙酮 在 aluminum (III) chloride 、 sodium tetrahydroborate 、 溴 、 potassium carbonate 作用下， 以 甲醇 、 乙醚 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 生成 4-(1-hydroxy-2-(2-methoxyphenoxy)ethyl)-2,6-dimethoxyphenol
  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

• Catalytic C(β)–O Bond Cleavage of Lignin in a One-Step Reaction Enabled by a Spin-Center Shift
  作者：Qilei Zhu、Daniel G. Nocera

  DOI：10.1021/acscatal.1c04008

  日期：2021.11.19

  A challenge to the utilization of lignin as a feedstock for aromatic fine chemicals lies in selective cleavage of copious β-O-4 linkages. A photocatalytic strategy for the selective cleavage of the C(β)–O bonds of model substrates and natural lignin extracts is achieved by a redox-neutral, catalytic cycle that does not require stoichiometric reagents. Mechanistic studies reveal the generation of a thiyl

  利用木质素作为芳香精细化学品原料的挑战在于大量 β- O -4 键的选择性裂解。选择性裂解模型底物和天然木质素提取物的 C(β)-O 键的光催化策略是通过不需要化学计量试剂的氧化还原中性催化循环实现的。机理研究揭示了硫自由基的产生，该自由基源自胱氨酸衍生的 H 原子转移催化剂，引发自旋中心位移 (SCS)，导致 C(β)-O 键断裂。SCS 反应性让人联想到发生在核糖核苷酸还原酶活性位点的 C(β)-O 键裂解化学反应。
• On the Reactions of Two Fungal Laccases Differing in Their Redox Potential with Lignin Model Compounds: Products and Their Rate of Formation
  作者：Maarit Lahtinen、Kristiina Kruus、Petri Heinonen、Jussi Sipilä

  DOI：10.1021/jf901511k

  日期：2009.9.23

  Laccases (EC 1.10.3.2) are multicopper oxidases able to oxidize phenolic compounds such as lignin-related polyphenols. Since the discovery that so-called mediators effectively extend the family of laccase substrates, direct interactions between lignin-like materials and laccase have gained much less attention. In this work, the aim was to characterize oxidation products formed in direct laccase-catalyzed oxidation of different guaiacylic and syringylic lignin model compounds with two different laccases: a low redox potential Melanocarpus albomyces laccase and a high redox potential Trametes hirsuta laccase. By following the formation of different, mainly biphenylic (5-5) and benzylic oxidation products, it was found that although both of these enzymes generated practically the same pattern of products with particular types of syringyl and guaiacyl compounds, in some cases a clear difference in the rates of their formation was observed. The results also confirm further to the suggestions that syringylic compounds are able to act as mediators in their own oxidation reactions and also that in some instances acetylation of phenolic material may produce altered, unexpected structures.
• Efficient Cobalt-Catalyzed Oxidative Conversion of Lignin Models to Benzoquinones
  作者：Berenger Biannic、Joseph J. Bozell

  DOI：10.1021/ol401065r

  日期：2013.6.7

  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.
• Adducts of anthrahydroquinone and anthranol with lignin model quinone methides. 1. Synthesis and characterization
  作者：Lawrence L. Landucci、John Ralph

  DOI：10.1021/jo00139a020

  日期：1982.8