4-(benzyloxy)-3-hydroxy-5-methoxybenzaldehyde | 1529796-54-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 4-(benzyloxy)-3-hydroxy-5-methoxybenzaldehyde
• 英文别名: 4-(Benzyloxy)-3-hydroxy-5-methoxybenzaldehyde；3-hydroxy-5-methoxy-4-phenylmethoxybenzaldehyde
• CAS: 1529796-54-0
• 化学式: C₁₅H₁₄O₄
• 分子量: 258.274
• InChiKey: LUNCRGZZVCFZFW-UHFFFAOYSA-N

物化性质

• 沸点：
  437.9±40.0 °C(Predicted)
• 密度：
  1.240±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-(benzyloxy)-3-hydroxy-5-methoxybenzaldehyde 在 copper(I) bromide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 2.5h， 生成 3-(benzyloxy)-4-hydroxy-5-methoxybenzaldehyde
  参考文献：
  名称：

  Unexpected copper mediated benzyl O→O migration during an Ullmann ether coupling

  摘要：

  The synthesis of a highly functionalized phenolic diaryl ether 5,5'-oxybis(4-hydroxy-3-methoxybenzaldehyde) (1) potentially interesting as a new scaffold for drug design, has been carried out using Ullmann coupling conditions. An unusual benzyl migration in o-benzyloxyphenol moiety occurred during this reaction leading to an unexpected compound identified as 4-(benzyloxy)-3-(2-(benzyloxy)-4-formy1-6-methoxyphenoxy)-5-methoxy benzaldehyde (7). A rationale for this migration process is proposed. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2013.11.089
• 作为产物：
  描述：

  3,4-二羟基-5-甲氧基苯甲醛 、 氯化苄 在 碳酸氢钠 、 sodium iodide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 16.0h， 以86%的产率得到4-(benzyloxy)-3-hydroxy-5-methoxybenzaldehyde
  参考文献：
  名称：

  Unexpected copper mediated benzyl O→O migration during an Ullmann ether coupling

  摘要：

  The synthesis of a highly functionalized phenolic diaryl ether 5,5'-oxybis(4-hydroxy-3-methoxybenzaldehyde) (1) potentially interesting as a new scaffold for drug design, has been carried out using Ullmann coupling conditions. An unusual benzyl migration in o-benzyloxyphenol moiety occurred during this reaction leading to an unexpected compound identified as 4-(benzyloxy)-3-(2-(benzyloxy)-4-formy1-6-methoxyphenoxy)-5-methoxy benzaldehyde (7). A rationale for this migration process is proposed. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2013.11.089

文献信息

• Synthesis and evaluation of antioxidant phenolic diaryl hydrazones as potent antiangiogenic agents in atherosclerosis
  作者：Corinne Vanucci-Bacqué、Caroline Camare、Chantal Carayon、Corinne Bernis、Michel Baltas、Anne Nègre-Salvayre、Florence Bedos-Belval

  DOI：10.1016/j.bmc.2016.05.067

  日期：2016.8

  atherogenesis, and subsequent toxicity, to prevent angiogenesis evoked by low oxidized LDL concentration (monitored by the formation of capillary tubes on Matrigel) and to inhibit intracellular ROS increase involved in the angiogenic signaling. A structure/activity study has been carried out and finally allowed to select the phenolic diaryl ether hydralazine derivative 2a, sharing all these protective properties

  衍生自二芳基和二芳基醚羟基苯甲醛框架1和2的一系列双hydr已被合成为潜在的抗氧化剂和抗血管生成剂，这是限制动脉粥样硬化和心血管事件所需的两个特性。对这些化合物的中和自由基形成，阻断内皮细胞诱导的低密度脂蛋白氧化（通过TBARS的形成进行监测），动脉粥样硬化形成的必要步骤以及随后的毒性（防止低氧化引起的血管生成）的能力进行了评估。 LDL浓度（通过在Matrigel上形成毛细管来监控）并抑制涉及血管生成信号的细胞内ROS的增加。进行了结构/活性研究，并最终选择了酚二芳基肼苯并肼衍生物2a共享所有这些保护特性，这对进一步开发很有希望。
• Unexpected copper mediated benzyl O→O migration during an Ullmann ether coupling
  作者：Corinne Vanucci-Bacqué、Slim Chaabouni、Isabelle Fabing、Florence Bedos-Belval、Michel Baltas

  DOI：10.1016/j.tetlet.2013.11.089

  日期：2014.1

  The synthesis of a highly functionalized phenolic diaryl ether 5,5'-oxybis(4-hydroxy-3-methoxybenzaldehyde) (1) potentially interesting as a new scaffold for drug design, has been carried out using Ullmann coupling conditions. An unusual benzyl migration in o-benzyloxyphenol moiety occurred during this reaction leading to an unexpected compound identified as 4-(benzyloxy)-3-(2-(benzyloxy)-4-formy1-6-methoxyphenoxy)-5-methoxy benzaldehyde (7). A rationale for this migration process is proposed. (C) 2013 Elsevier Ltd. All rights reserved.