(E)-3-(2,4-bis(allyloxy)phenyl)acrylic acid | 32406-37-4

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: (E)-3-(2,4-bis(allyloxy)phenyl)acrylic acid
• 英文别名: 2.4-Diallyloxyzimtsaeure
• CAS: 32406-37-4
• 化学式: C₁₅H₁₆O₄
• 分子量: 260.29
• InChiKey: IOAKMRGTVKSMTN-SOFGYWHQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.91
• 重原子数：
  19.0
• 可旋转键数：
  8.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  55.76
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  o-hydroxyacetophenone isonicotinoyl hydrazone 、 (E)-3-(2,4-bis(allyloxy)phenyl)acrylic acid 在 吡啶 、 三氯氧磷 作用下， 以44%的产率得到2-((E)-1-(2-isonicotinoylhydrazono)ethyl)phenyl (E)-3-(2,4-bis(allyloxy)phenyl)acrylate
  参考文献：
  名称：

  A multifunctional, light-activated prochelator inhibits UVA-induced oxidative stress

  摘要：

  UVA radiation can damage cells and tissues by direct photodamage of biomolecules as well as by initiating metal-catalyzed oxidative stress. In order to alleviate both concerns simultaneously, we synthesized a multifunctional prochelator PC-HAPI (2-((E)-1-(2-isonicotinoylhydrazono) ethyl)phenyl(trans)-3-(2,4-dihydroxyphenyl)acrylate) that contains a trans-(o-hydroxy)cinnamate ester photocleavable protecting group that is cleaved upon UVA exposure to release a coumarin, umbelliferone, and an aroylhydrazone metal chelator, HAPI (N'-[1-(2-hydroxyphenyl)ethyliden]isonicotinoylhydrazide). While the prochelator PC-HAPI exhibits negligible affinity for iron, it responds rapidly to UVA irradiation and converts to an iron-binding chelator that inhibits iron-catalyzed formation of reactive oxygen species and protects cells from UVA damage. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2015.06.048
• 作为产物：
  描述：

  ethyl (E)-3-(2,4-bis(allyloxy)phenyl)acrylate 在 sodium hydroxide 作用下， 以 甲醇 、 水 为溶剂， 以100%的产率得到(E)-3-(2,4-bis(allyloxy)phenyl)acrylic acid
  参考文献：
  名称：

  A multifunctional, light-activated prochelator inhibits UVA-induced oxidative stress

  摘要：

  UVA radiation can damage cells and tissues by direct photodamage of biomolecules as well as by initiating metal-catalyzed oxidative stress. In order to alleviate both concerns simultaneously, we synthesized a multifunctional prochelator PC-HAPI (2-((E)-1-(2-isonicotinoylhydrazono) ethyl)phenyl(trans)-3-(2,4-dihydroxyphenyl)acrylate) that contains a trans-(o-hydroxy)cinnamate ester photocleavable protecting group that is cleaved upon UVA exposure to release a coumarin, umbelliferone, and an aroylhydrazone metal chelator, HAPI (N'-[1-(2-hydroxyphenyl)ethyliden]isonicotinoylhydrazide). While the prochelator PC-HAPI exhibits negligible affinity for iron, it responds rapidly to UVA irradiation and converts to an iron-binding chelator that inhibits iron-catalyzed formation of reactive oxygen species and protects cells from UVA damage. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2015.06.048