2-((4-methoxybenzyl)oxy)ethyl benzoate | 1352444-30-4

• 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: 2-((4-methoxybenzyl)oxy)ethyl benzoate
• 英文别名: 2-[(4-Methoxyphenyl)methoxy]ethyl benzoate；2-[(4-methoxyphenyl)methoxy]ethyl benzoate
• CAS: 1352444-30-4
• 化学式: C₁₇H₁₈O₄
• 分子量: 286.328
• InChiKey: ALJJTSPEOGAYJD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  21
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-((4-methoxybenzyl)oxy)ethyl benzoate 在 sodium hydrogen sulfate 、 eosin 、 双氧水 作用下， 以 水 、 乙腈 为溶剂， 反应 25.0h， 以73%的产率得到乙二醇单苯并酸酯
  参考文献：
  名称：

  以过氧化氢为末端氧化剂的光氧化还原对甲氧基苄基醚保护基

  摘要：

  AbstractWe report a mild protocol for removal of the p‐methoxybenzyl ether protecting group under acidic conditions with eosin Y combined with LEDs as a photoredox catalysis system and hydrogen peroxide as the terminal oxidant. This protocol is compatible with ethers derived from primary, secondary, and tertiary alcohols, as well as with various functional groups. The protocol showed unusual selectivity for a tertiary ether over a primary ether. The scale up to gram scale is also explored and identical reactivity is observed.magnified image

  DOI：

  10.1002/adsc.201400936
• 作为产物：
  描述：

  乙二醇单苯并酸酯 、 4-甲氧基氯苄 在 N,N-二异丙基乙胺 作用下， 反应 1.0h， 以91%的产率得到2-((4-methoxybenzyl)oxy)ethyl benzoate
  参考文献：
  名称：

  以叔胺为基础的羟基苯甲酸酯化

  摘要：

  描述了在叔胺存在下羟基的苄基化。在二异丙基乙胺的存在下，醇和苄基卤的混合物以良好或优异的产率提供了相应的苄基醚。观察到无溶剂条件的重要性。该反应即使在150℃的反应温度下也显示出对包括苯甲酸酯在内的许多官能团的高耐受性。发现碘化钠是加速反应的有效催化剂。

  DOI：

  10.1016/j.tet.2011.10.016

文献信息

• Benzylation of hydroxy groups with tertiary amine as a base
  作者：Jeremiah W. Gathirwa、Toshihide Maki

  DOI：10.1016/j.tet.2011.10.016

  日期：2012.1

  The benzylation of hydroxy groups in the presence of tertiary amines is described. A mixture of an alcohol and a benzyl halide afforded the corresponding benzyl ether in good to excellent yields in the presence of diisopropylethylamine. The importance of solventless conditions was observed. The reaction showed high tolerance to many functional groups including benzoate, even at a reaction temperature

  描述了在叔胺存在下羟基的苄基化。在二异丙基乙胺的存在下，醇和苄基卤的混合物以良好或优异的产率提供了相应的苄基醚。观察到无溶剂条件的重要性。该反应即使在150℃的反应温度下也显示出对包括苯甲酸酯在内的许多官能团的高耐受性。发现碘化钠是加速反应的有效催化剂。
• Photoredox Removal of<i>p</i>-Methoxybenzyl Ether Protecting Group with Hydrogen Peroxide as Terminal Oxidant
  作者：Zheng Liu、Yi Zhang、Zheren Cai、Hao Sun、Xu Cheng

  DOI：10.1002/adsc.201400936

  日期：2015.2.9

  AbstractWe report a mild protocol for removal of the p‐methoxybenzyl ether protecting group under acidic conditions with eosin Y combined with LEDs as a photoredox catalysis system and hydrogen peroxide as the terminal oxidant. This protocol is compatible with ethers derived from primary, secondary, and tertiary alcohols, as well as with various functional groups. The protocol showed unusual selectivity for a tertiary ether over a primary ether. The scale up to gram scale is also explored and identical reactivity is observed.magnified image