3-<3,4-bis(octanoyloxy)cyclohexyl>-2-propen-1-al | 127540-51-6

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 3-<3,4-bis(octanoyloxy)cyclohexyl>-2-propen-1-al
• 英文别名: 3-(3,4-bis(octanoyloxy)cyclohexyl)-2-propen-1-al
• CAS: 127540-51-6
• 化学式: C₂₅H₄₂O₅
• 分子量: 422.605
• InChiKey: SRIAFVQHGFLSBW-RJGXRXQPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.09
• 重原子数：
  30.0
• 可旋转键数：
  16.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  69.67
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  3-<3,4-bis(octanoyloxy)cyclohexyl>-2-propen-1-al 在 dibutylacetyltin oxide 、 poly(methoxyhydrosilane) 作用下， 以 乙醇 为溶剂， 反应 1.5h， 生成 3-<3,4-bis(octanoyloxy)cyclohexyl>-2-propen-1-ol
  参考文献：
  名称：

  Cyclohexane diester analogs of phorbol ester as potential activators of protein kinase C

  摘要：

  Phospholipid-dependent, Ca2(+)-sensitive protein kinase (protein kinase C) is activated by the plant product phorbol ester at nanomolar concentrations and also in vivo at micromolar concentrations by diacylglycerols. We designed and synthesized cyclohexane diester analogues of the phorbol ester C ring as potential high-affinity activators of protein kinase C. We proposed that the necessary pharmacophore of phorbol ester could be mimicked by diesters of appropriately substituted cyclohexanediols. A series of 1,2-cyclohexanediol diesters with different substituents at position 4 was synthesized. These substituents were designed to mimic the 6,7-double bond and C-20 hydroxy of phorbol ester. Competitive binding vs [3H]phorbol dibutyrate determined that these compounds have an affinity for protein kinase C of 1 mM or more, and thus they do not bind to nor are they activators of this enzyme.

  DOI：

  10.1021/jm00169a023
• 作为产物：
  描述：

  3-环己烯甲醛 在 吡啶 、 四氧化锇 、 Amberlyst 15 、 N-甲基吗啉氧化物 作用下， 以 四氢呋喃 、 氯仿 、 水 、 甲苯 、 三氟乙酸 为溶剂， 反应 20.0h， 生成 3-<3,4-bis(octanoyloxy)cyclohexyl>-2-propen-1-al
  参考文献：
  名称：

  Cyclohexane diester analogs of phorbol ester as potential activators of protein kinase C

  摘要：

  Phospholipid-dependent, Ca2(+)-sensitive protein kinase (protein kinase C) is activated by the plant product phorbol ester at nanomolar concentrations and also in vivo at micromolar concentrations by diacylglycerols. We designed and synthesized cyclohexane diester analogues of the phorbol ester C ring as potential high-affinity activators of protein kinase C. We proposed that the necessary pharmacophore of phorbol ester could be mimicked by diesters of appropriately substituted cyclohexanediols. A series of 1,2-cyclohexanediol diesters with different substituents at position 4 was synthesized. These substituents were designed to mimic the 6,7-double bond and C-20 hydroxy of phorbol ester. Competitive binding vs [3H]phorbol dibutyrate determined that these compounds have an affinity for protein kinase C of 1 mM or more, and thus they do not bind to nor are they activators of this enzyme.

  DOI：

  10.1021/jm00169a023