dehydrodiapocynol | 84316-14-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: dehydrodiapocynol
• 英文别名: 5,5'-Bis(1-hydroxyethyl)-3,3'-dimethoxy-2,2'-biphenyldiol；4-(1-hydroxyethyl)-2-[2-hydroxy-5-(1-hydroxyethyl)-3-methoxyphenyl]-6-methoxyphenol
• CAS: 84316-14-3
• 化学式: C₁₈H₂₂O₆
• 分子量: 334.369
• InChiKey: OSZDMJSRVJDDEU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  24
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  99.4
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  反式-3-(4-羟基-3-甲氧基苯基)-2-丙烯-1-醇 、 dehydrodiapocynol 在 双氧水 、 horseradish peroxidase 作用下， 以 phosphate buffer 、 丙酮 为溶剂， 反应 14.0h， 生成
  参考文献：
  名称：

  Regioselectivity in oxidative cross-coupling of phenols. Application to the synthesis of dimeric neolignans

  摘要：

  The problems of regioselectivity in oxidative coupling of phenols are outlined, and recent research on the application to the synthesis of lignans and neolignans is reviewed. Lignans and neolignans are dimers that are typically formed by oxidative coupling of propenyl phenols. The coupling of structurally different phenols (cross-coupling) is an extension of this synthesis. Recent results show that cross-coupling can be achieved if the phenols have compatible reactivities. The regioselectivity is often quite different in cross-coupling compared to dimerization. Coupling of phenols with widely different rates of oxidation is difficult but can be achieved if the concentration of the more reactive phenol can be kept low enough during the reaction, for instance by diffusion through a dialysis membrane. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(00)00943-1
• 作为产物：
  描述：

  香草乙酮 在 sodium tetrahydroborate 、 双氧水 、 horseradish peroxidase 作用下， 以 乙醇 、 水 为溶剂， 反应 16.0h， 生成 dehydrodiapocynol
  参考文献：
  名称：

  Regioselectivity in oxidative cross-coupling of phenols. Application to the synthesis of dimeric neolignans

  摘要：

  The problems of regioselectivity in oxidative coupling of phenols are outlined, and recent research on the application to the synthesis of lignans and neolignans is reviewed. Lignans and neolignans are dimers that are typically formed by oxidative coupling of propenyl phenols. The coupling of structurally different phenols (cross-coupling) is an extension of this synthesis. Recent results show that cross-coupling can be achieved if the phenols have compatible reactivities. The regioselectivity is often quite different in cross-coupling compared to dimerization. Coupling of phenols with widely different rates of oxidation is difficult but can be achieved if the concentration of the more reactive phenol can be kept low enough during the reaction, for instance by diffusion through a dialysis membrane. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(00)00943-1

文献信息

• 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。