1-(3,4-二甲氧基苯基)-2-(4-甲氧基苯基)丙烷-1,3-二醇 | 97451-25-7

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 中文名称: 1-(3,4-二甲氧基苯基)-2-(4-甲氧基苯基)丙烷-1,3-二醇
• 英文名称: 1-(3,4-dimethoxyphenyl)-2-(4-methoxyphenyl)-1,3-propanediol
• 英文别名: 1-(3,4-dimethoxyphenyl)-2-(4-methoxyphenyl)-propane-1,3-diol；1-(3,4-Dimethoxyphenyl)-2-(4-methoxyphenyl)propane-1,3-diol
• CAS: 97451-25-7
• 化学式: C₁₈H₂₂O₅
• 分子量: 318.37
• InChiKey: PMAHFMBORXFDDC-UHFFFAOYSA-N

物化性质

• 沸点：
  500.3±50.0 °C(Predicted)
• 密度：
  1.188±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  23
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  68.2
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1-(3,4-二甲氧基苯基)-2-(4-甲氧基苯基)丙烷-1,3-二醇 在 lithium aluminium tetrahydride 、 正丁基锂 、 9,10-二氰基蒽 、 lignin peroxidase 、 双氧水 、 氧气 、 二异丙胺 作用下， 以 四氢呋喃 、 水 、 乙腈 为溶剂， 反应 14.5h， 生成 2-羟基苯乙酮
  参考文献：
  名称：

  Photochemical and enzymatic SET promoted C–C bond cleavage reactions of lignin β-1 model compounds containing varying number of methoxy substituents on their arene rings

  摘要：

  In the current study, 1,2-diarylpropan-1,3-diols, containing varying numbers of methoxy substituents that mimic beta-1 type units in lignins, were prepared and subjected to photochemical and enzymatic SET oxidative C-C bond cleavage reactions to explore how product distributions and reactivity profiles depend on the numbers and positions of arene ring methoxy-substituents. For this purpose, product distributions of SET-promoted photochemical reactions of the beta-1 model compounds and the characteristics of lignin peroxidase catalyzed bond cleavage reactions of these substances were explored. The results show that both the photochemical and enzymatic reactions, which are known to occur by initial SET to form arylpropanoid cation radicals, generate predominantly aldehydes and beta-hydroxyketones through cation radical C1-C2 bond cleavage pathways. In addition, analysis of the relative quantum efficiencies of the SET photochemical processes shows that they do not depend greatly on the numbers and positions of arene ring methoxy substituents of the beta-1 model compounds. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2015.04.077
• 作为产物：
  描述：

  1,2-双(3,4-二甲氧基苯基)丙烷-1,3-二醇 在 咪唑 、 lithium aluminium tetrahydride 、 正丁基锂 、 9,10-二氰基蒽 、 四丁基氟化铵 、 氧气 、 二异丙胺 作用下， 以 四氢呋喃 、 水 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 28.0h， 生成 1-(3,4-二甲氧基苯基)-2-(4-甲氧基苯基)丙烷-1,3-二醇
  参考文献：
  名称：

  Photochemical and enzymatic SET promoted C–C bond cleavage reactions of lignin β-1 model compounds containing varying number of methoxy substituents on their arene rings

  摘要：

  In the current study, 1,2-diarylpropan-1,3-diols, containing varying numbers of methoxy substituents that mimic beta-1 type units in lignins, were prepared and subjected to photochemical and enzymatic SET oxidative C-C bond cleavage reactions to explore how product distributions and reactivity profiles depend on the numbers and positions of arene ring methoxy-substituents. For this purpose, product distributions of SET-promoted photochemical reactions of the beta-1 model compounds and the characteristics of lignin peroxidase catalyzed bond cleavage reactions of these substances were explored. The results show that both the photochemical and enzymatic reactions, which are known to occur by initial SET to form arylpropanoid cation radicals, generate predominantly aldehydes and beta-hydroxyketones through cation radical C1-C2 bond cleavage pathways. In addition, analysis of the relative quantum efficiencies of the SET photochemical processes shows that they do not depend greatly on the numbers and positions of arene ring methoxy substituents of the beta-1 model compounds. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2015.04.077