(E)-3-(5-hydroxytetrahydrofuran-2-yl)acrylaldehyde

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧唑烯
• 英文名称: (E)-3-(5-hydroxytetrahydrofuran-2-yl)acrylaldehyde
• 英文别名: (E)-3-(5-hydroxyoxolan-2-yl)prop-2-enal
• 化学式: C₇H₁₀O₃
• 分子量: 142.155
• InChiKey: LCECCDHDQDTSMX-OWOJBTEDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.2
• 重原子数：
  10
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (E)-3-(5-hydroxytetrahydrofuran-2-yl)acrylaldehyde 在 pyridinium chlorochromate 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 以45%的产率得到(E)-3-(5-oxotetrahydrofuran-2-yl)acrylaldehyde
  参考文献：
  名称：

  Fe²⁺ Catalyzes Vitamin E-Induced Fragmentation of Hydroperoxy and Hydroxy Endoperoxides That Generates γ-Hydroxy Alkenals

  摘要：

  The formation of cytotoxic gamma-hydroxyalkenals has been generally viewed as the consequence of free radical-induced oxidation of polyunsaturated fatty acyls through the decomposition of lipid peroxides. Vitamin E (Vit E) would be expected to inhibit such autoxidation. In a model study, we now find that fragmentation of a hydroperoxy endoperoxide generated the lactone of a gamma-hydroxyalkenal. With 1 equiv of Fe2+, or with a catalytic amount (0.1 equiv) of Fe2+ and 1 equiv of Vit E, the yields are 43-50%. However, Vit E alone did not promote the fragmentation, and a catalytic amount of Fe2+ alone only afforded a low yield (about 5%). Vit E could contribute to, as opposed to preventing, the formation of gamma-hydroxyalkenals by converting redox-active metal ions into their reduced forms that promote the rapid fragmentation of hydroperoxy endoperoxides.

  DOI：

  10.1021/ja0689785
• 作为产物：
  描述：

  环庚三烯 在 氨 、 氧气 、 tetraphenylporphyrin 、 lithium 、 iron(II) sulfate 、 三苯基膦 作用下， 以 二氯甲烷 、 水 、 乙腈 为溶剂， 反应 14.33h， 生成 (E)-3-(5-hydroxytetrahydrofuran-2-yl)acrylaldehyde
  参考文献：
  名称：

  Fe²⁺ Catalyzes Vitamin E-Induced Fragmentation of Hydroperoxy and Hydroxy Endoperoxides That Generates γ-Hydroxy Alkenals

  摘要：

  The formation of cytotoxic gamma-hydroxyalkenals has been generally viewed as the consequence of free radical-induced oxidation of polyunsaturated fatty acyls through the decomposition of lipid peroxides. Vitamin E (Vit E) would be expected to inhibit such autoxidation. In a model study, we now find that fragmentation of a hydroperoxy endoperoxide generated the lactone of a gamma-hydroxyalkenal. With 1 equiv of Fe2+, or with a catalytic amount (0.1 equiv) of Fe2+ and 1 equiv of Vit E, the yields are 43-50%. However, Vit E alone did not promote the fragmentation, and a catalytic amount of Fe2+ alone only afforded a low yield (about 5%). Vit E could contribute to, as opposed to preventing, the formation of gamma-hydroxyalkenals by converting redox-active metal ions into their reduced forms that promote the rapid fragmentation of hydroperoxy endoperoxides.

  DOI：

  10.1021/ja0689785

文献信息

• Fe²⁺ Catalyzes Vitamin E-Induced Fragmentation of Hydroperoxy and Hydroxy Endoperoxides That Generates γ-Hydroxy Alkenals
  作者：Xiaodong Gu、Wujuan Zhang、Robert G. Salomon

  DOI：10.1021/ja0689785

  日期：2007.5.1

  The formation of cytotoxic gamma-hydroxyalkenals has been generally viewed as the consequence of free radical-induced oxidation of polyunsaturated fatty acyls through the decomposition of lipid peroxides. Vitamin E (Vit E) would be expected to inhibit such autoxidation. In a model study, we now find that fragmentation of a hydroperoxy endoperoxide generated the lactone of a gamma-hydroxyalkenal. With 1 equiv of Fe2+, or with a catalytic amount (0.1 equiv) of Fe2+ and 1 equiv of Vit E, the yields are 43-50%. However, Vit E alone did not promote the fragmentation, and a catalytic amount of Fe2+ alone only afforded a low yield (about 5%). Vit E could contribute to, as opposed to preventing, the formation of gamma-hydroxyalkenals by converting redox-active metal ions into their reduced forms that promote the rapid fragmentation of hydroperoxy endoperoxides.