4a-((E)-9-Iodo-non-8-enyl)-6,7-dimethoxy-8a-methyl-1,4,4a,8a-tetrahydro-1,4-methano-naphthalene-5,8-dione | 596828-53-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4a-((E)-9-Iodo-non-8-enyl)-6,7-dimethoxy-8a-methyl-1,4,4a,8a-tetrahydro-1,4-methano-naphthalene-5,8-dione
• CAS: 596828-53-4
• 化学式: C₂₃H₃₁IO₄
• 分子量: 498.401
• InChiKey: CIHRZJQSCIVVEJ-UHFFFAOYSA-N

物化性质

• 沸点：
  550.5±50.0 °C(Predicted)
• 密度：
  1.39±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.52
• 重原子数：
  28.0
• 可旋转键数：
  10.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  52.6
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  4a-((E)-9-Iodo-non-8-enyl)-6,7-dimethoxy-8a-methyl-1,4,4a,8a-tetrahydro-1,4-methano-naphthalene-5,8-dione 在 sodium dithionite 作用下， 以 正己烷 、 甲苯 为溶剂， 反应 2.0h， 生成 2-((E)-9-Iodo-non-8-enyl)-5,6-dimethoxy-3-methyl-benzene-1,4-diol
  参考文献：
  名称：

  Synthesis and inhibitory activity of ubiquinone–acetogenin hybrid inhibitor with bovine mitochondrial complex I

  摘要：

  To elucidate the inhibitory action of acetogenins, the most potent inhibitors of mitochondrial complex I, we synthesized an acetogenin analogue which possesses a ubiquinone ring (i.e., the physiological substrate of complex I) in place of the alpha,beta-unsaturated gamma-lactone ring of natural acetogenins, and named it Q-acetogenin. Our results indicate that the gamma-lactone ring of acetogenins is completely substitutable with the ubiquinone ring. This fact is discussed in light of the inhibitory action of acetogenins. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(03)00439-6
• 作为产物：
  描述：

  (E,Z)-1,9-diiodonon-1-ene 、 4,5-dimethoxy-2-methyltricyclo[6.2.1.0^2,7]undeca-4,9-diene-3,6-dione 在 potassium tert-butylate 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 以65%的产率得到4a-((E)-9-Iodo-non-8-enyl)-6,7-dimethoxy-8a-methyl-1,4,4a,8a-tetrahydro-1,4-methano-naphthalene-5,8-dione
  参考文献：
  名称：

  Synthesis and inhibitory activity of ubiquinone–acetogenin hybrid inhibitor with bovine mitochondrial complex I

  摘要：

  To elucidate the inhibitory action of acetogenins, the most potent inhibitors of mitochondrial complex I, we synthesized an acetogenin analogue which possesses a ubiquinone ring (i.e., the physiological substrate of complex I) in place of the alpha,beta-unsaturated gamma-lactone ring of natural acetogenins, and named it Q-acetogenin. Our results indicate that the gamma-lactone ring of acetogenins is completely substitutable with the ubiquinone ring. This fact is discussed in light of the inhibitory action of acetogenins. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(03)00439-6