1-(3-(ethoxymethoxy)-4-methoxyphenyl)-2-(3,4,5-trimethoxyphenyl)ethanol | 956699-47-1

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: 1-(3-(ethoxymethoxy)-4-methoxyphenyl)-2-(3,4,5-trimethoxyphenyl)ethanol
• 英文别名: 1-[3-(Ethoxymethoxy)-4-methoxyphenyl]-2-(3,4,5-trimethoxyphenyl)ethanol
• CAS: 956699-47-1
• 化学式: C₂₁H₂₈O₇
• 分子量: 392.449
• InChiKey: BOTZGGVWRXUAQC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  28
• 可旋转键数：
  11
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  75.6
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  1-(3-(ethoxymethoxy)-4-methoxyphenyl)-2-(3,4,5-trimethoxyphenyl)ethanol 在 盐酸 作用下， 以 1,4-二氧六环 为溶剂， 反应 1.0h， 以82%的产率得到trans-combretastatin A-4
  参考文献：
  名称：

  Ion pairing effects on the regioselectivity of arylic versus benzylic C–O bond reductive cleavage: synthetic applications

  摘要：

  The regioselectivity of the reductive cleavage of 3,4,5-trimethoxybenzyl methyl ether strongly depends on the alkali metal employed as a reducing agent and solvent effects. Reactions run using Na as a reducing agent led to aromatic C(4)-O bond cleavage, whilst reductions run in the presence of Na/15-crown-5, or using Li as a reducing agent, led to highly regioselective benzylic C-O bond cleavage. This regioselectivity turnaround is discussed in terms of major solvent effects affecting the fragmentation paths of a common reaction intermediate. Synthetic applications of these findings led to the synthesis of biologically active compounds, like 2,5-dialkyl-substituted resorcinols, or 1-(3,4,5-trimethoxyphenyl)-2-arylethanes structurally related to combretastatin. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2007.09.010
• 作为产物：
  描述：

  1,2,3-三甲氧基-5-(甲氧基甲基)苯 、 3-(ethoxymethoxy)-4-methoxybenzaldehyde 在 萘 、 lithium 作用下， 以 四氢呋喃 为溶剂， 反应 0.33h， 以65%的产率得到1-(3-(ethoxymethoxy)-4-methoxyphenyl)-2-(3,4,5-trimethoxyphenyl)ethanol
  参考文献：
  名称：

  Ion pairing effects on the regioselectivity of arylic versus benzylic C–O bond reductive cleavage: synthetic applications

  摘要：

  The regioselectivity of the reductive cleavage of 3,4,5-trimethoxybenzyl methyl ether strongly depends on the alkali metal employed as a reducing agent and solvent effects. Reactions run using Na as a reducing agent led to aromatic C(4)-O bond cleavage, whilst reductions run in the presence of Na/15-crown-5, or using Li as a reducing agent, led to highly regioselective benzylic C-O bond cleavage. This regioselectivity turnaround is discussed in terms of major solvent effects affecting the fragmentation paths of a common reaction intermediate. Synthetic applications of these findings led to the synthesis of biologically active compounds, like 2,5-dialkyl-substituted resorcinols, or 1-(3,4,5-trimethoxyphenyl)-2-arylethanes structurally related to combretastatin. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2007.09.010

文献信息

• Ion pairing effects on the regioselectivity of arylic versus benzylic C–O bond reductive cleavage: synthetic applications
  作者：Ugo Azzena、Giovanna Dettori、Ilaria Mascia、Luisa Pisano、Mario Pittalis

  DOI：10.1016/j.tet.2007.09.010

  日期：2007.11

  The regioselectivity of the reductive cleavage of 3,4,5-trimethoxybenzyl methyl ether strongly depends on the alkali metal employed as a reducing agent and solvent effects. Reactions run using Na as a reducing agent led to aromatic C(4)-O bond cleavage, whilst reductions run in the presence of Na/15-crown-5, or using Li as a reducing agent, led to highly regioselective benzylic C-O bond cleavage. This regioselectivity turnaround is discussed in terms of major solvent effects affecting the fragmentation paths of a common reaction intermediate. Synthetic applications of these findings led to the synthesis of biologically active compounds, like 2,5-dialkyl-substituted resorcinols, or 1-(3,4,5-trimethoxyphenyl)-2-arylethanes structurally related to combretastatin. (C) 2007 Elsevier Ltd. All rights reserved.