1-(4-hydroxy-3-methoxyphenyl)-2-{4-[(E)-3-hydroxy-1-propenyl]-2-methoxyphenoxy}-1,3-propanediol | 261778-30-7

• 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-{4-[(E)-3-hydroxy-1-propenyl]-2-methoxyphenoxy}-1,3-propanediol
• 英文别名: 1-(4-hydroxy-3-methoxyphenyl)-2-{2-methoxy-4-[1-(E)-propen-3-ol]-phenoxy}-propane-1,3-diol；guaiacylglycerol-β-O-4'-synapyl ether；1-(4-hydroxy-3-methoxyphenyl)-2-[2-methoxy-4-(1-(E)-propen-3-ol)-phenoxy]-propane-1,3-diol；Ggbce；1-(4-hydroxy-3-methoxyphenyl)-2-[4-[(E)-3-hydroxyprop-1-enyl]-2-methoxyphenoxy]propane-1,3-diol
• CAS: 261778-30-7
• 化学式: C₂₀H₂₄O₇
• 分子量: 376.406
• InChiKey: FYEZJIXULOZDRT-ONEGZZNKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  27
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  109
• 氢给体数：
  4
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  1-(4-hydroxy-3-methoxyphenyl)-2-{4-[(E)-3-hydroxy-1-propenyl]-2-methoxyphenoxy}-1,3-propanediol 在 nickel boride 氢气 作用下， 以 1,4-二氧六环 为溶剂， 生成 1-(4-hydroxy-3-methoxyphenyl)-2-<4-(ω-hydroxypropyl-2-methoxy)-phenoxy>-propane-1,3-diol
  参考文献：
  名称：

  Freudenberg,K. et al., Chemische Berichte, 1964, vol. 97, p. 909 - 920

  摘要：

  DOI：
• 作为产物：
  描述：

  反式-3-(4-羟基-3-甲氧基苯基)-2-丙烯-1-醇 生成 1-(4-hydroxy-3-methoxyphenyl)-2-{4-[(E)-3-hydroxy-1-propenyl]-2-methoxyphenoxy}-1,3-propanediol
  参考文献：
  名称：

  Freudenberg,K.; Lehmann,B., Chemische Berichte, 1960, vol. 93, p. 1354 - 1366

  摘要：

  DOI：

文献信息

• Synthesis and Characterization of New 5-Linked Pinoresinol Lignin Models
  作者：Fengxia Yue、Fachuang Lu、Runcang Sun、John Ralph

  DOI：10.1002/chem.201201506

  日期：2012.12.14

  alcohol producing pinoresinol‐containing trimers (and higher oligomers) in addition to other homo‐ and cross‐coupled products. Eight new lignin model compounds were obtained and characterized by NMR spectroscopy, and one tentatively identified cross‐coupled β‐O‐4′‐product was formed from a coniferyl alcohol 5‐O‐4′‐linked dimer. It was demonstrated that the 5‐5′‐ and 5‐O‐4′‐linked pinoresinol structures could

  松脂醇结构具有木质素单体单元之间的β-β'键，在软木木质素以及双子叶植物和单子叶植物中，特别是在丁香基特异性基因中被下调的那些中，都非常重要。虽然容易通过NMR光谱检测，松脂醇结构主要由β-醚裂解降解逃过检测分析推测由于联系的在5个位置的存在下，在5-5'-或5- ö -4'-结构。在这项研究中，旨在通过提供NMR表征所需的数据来帮助更好地理解5-连接的松脂醇结构，新的木质素模型化合物是通过仿生过氧化物酶介导的预制（游离酚）松柏树醇之间的氧化偶联反应合成的5‐5′‐或5‐ O‐4′-连接的二聚体和松柏醇单体。结果发现，除其他均相和交联产物外，此类含有游离酚类松柏醇部分的二聚体还可与产生松柏醇的三聚松脂（及高级低聚物）的松柏醇交叉偶联。获得和表征通过NMR谱八个新木质素模型化合物，和一种初步确定交叉耦合β -O- 4'-产物从一个松柏醇形成5- ö -4'-连接的二聚体。证明了5‐5′‐和5‐
• Regioselectivity in lignin biosynthesis. The influence of dimerization and cross-coupling
  作者：Kaisa Syrjänen、Gösta Brunow

  DOI：10.1039/a907919j

  日期：——

  We have studied the regioselectivity of oxidative phenol coupling in lignin formation using an oxidation system that distinguishes between dimerization reactions and cross-coupling reactions. We found that the regioselectivity of coupling was different in the two reactions. For instance, in coniferyl alcohol dimerization the formation of β–5 coupling product has a slight prevalence over the formation of β–O-4 product; in cross-coupling the β–O-4 mode is favoured in a ratio of ≈10∶1. This ratio is higher than that found in isolated softwood lignins. The degree of cross-coupling was influenced only to a small extent by changes in the rates of conventional addition of coniferyl alcohol (Zulauf versus Zutropf conditions). We found that diffusion through a dialysis membrane did effectively suppress the dimerization of coniferyl alcohol. Of the different oxidants investigated, manganese triacetate in acetic acid yielded the highest proportion of cross-coupling product.

  我们利用一种区分二聚反应和交叉偶联反应的氧化体系，研究了木质素形成过程中氧化酚偶联的区域选择性。我们发现，在这两种反应中，偶联的区域选择性是不同的。例如，在针叶醇二聚反应中，β-5 偶联产物的形成略优于 β-O-4 产物的形成；而在交叉偶联反应中，β-O-4 模式的比例为 ≈10∶1。这一比例高于在分离的软木木质素中发现的比例。交叉偶联的程度仅在很小程度上受到针叶醇常规添加速率变化（祖劳夫条件与祖特洛夫条件）的影响。我们发现，通过透析膜的扩散确实有效地抑制了松柏醇的二聚化。在所研究的不同氧化剂中，乙酸中的三乙酸锰产生的交叉偶联产物比例最高。
• Lignans of Larix leptolepis
  作者：Keji Miki、Takashi Takehara、Takashi Sasaya、Akira Sakakibara

  DOI：10.1016/0031-9422(80)83199-2

  日期：1980.1

  Abstract Five lignans have been isolated from wood of Larix leptolepis . They are identified as 1-(4-hydroxy-3-methoxyphenyl)-2-4-[2-formyl-( E )-vinyl]-2-methoxyphenoxy-propane- 1,3-diol, 1-(4-hydroxy-3-methoxyphenyl)-2-2-methoxy-4-[1-( E )-propen-3-ol]-phenoxy- propane-1,3-diol, 1-(4-hydroxy-3-methoxyphenyl)-2-(4-formyl-2-methoxyphenoxy)-propane-1,3-diol, 1,2-bis-(4-hydroxy-3-methoxyphenyl)-propane-1

  摘要 从落叶松木材中分离到了五种木脂素。它们被鉴定为 1-(4-羟基-3-甲氧基苯基)-2-4-[2-甲酰基-(E)-乙烯基]-2-甲氧基苯氧基-丙烷-1,3-二醇，1-(4-羟基-3-甲氧基苯基)-2-2-甲氧基-4-[1-(E)-丙烯-3-醇]-苯氧基-丙烷-1,3-二醇，1-(4-羟基-3-甲氧基苯基)- 2-(4-甲酰基-2-甲氧基苯氧基)-丙烷-1,3-二醇、1,2-双-(4-羟基-3-甲氧基苯基)-丙烷-1,3-二醇和三木质素、leptolepisol C.
• Salen complexes with bulky substituents as useful tools for biomimetic phenol oxidation research
  作者：Anssi Haikarainen、Jussi Sipilä、Pekka Pietikäinen、Aarne Pajunen、Ilpo Mutikainen

  DOI：10.1016/s0968-0896(01)00053-0

  日期：2001.6

  The catalytic properties of bulky water-soluble Co-, Cu-, Fe- and Mn-salen complexes in the oxidation of phenolic lignin model compounds have been studied in aqueous water-dioxane solutions (pH 3-10). Mn catalysts were found to oxidize coniferyl alcohol in a same reaction time as horseradish peroxidase (HRP) enzyme and Mn and Co catalysts showed different regioselectivity suggesting a different substrate to catalyst interaction in the oxidative coupling. When the oxidation of material more relevant to plant polyphenolics was studied, the results indicated that the complexes catalyze one- and two-electron oxidations depending on the bulk of the substrate. (C) 2001 Elsevier Science Ltd. All rights reserved.
• Syrjaenen, Kaisa; Brunow, Goesta, Journal of the Chemical Society. Perkin transactions I, 1998, # 20, p. 3425 - 3429
  作者：Syrjaenen, Kaisa、Brunow, Goesta

  DOI：——

  日期：——