methyl 2-(3,7-dimethylocta-2,6-dienyl)-3,5-dihydroxybenzoate | 1075694-33-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: methyl 2-(3,7-dimethylocta-2,6-dienyl)-3,5-dihydroxybenzoate
• 英文别名: methyl 2-[(2E)-3,7-dimethylocta-2,6-dienyl]-3,5-dihydroxybenzoate
• CAS: 1075694-33-5
• 化学式: C₁₈H₂₄O₄
• 分子量: 304.386
• InChiKey: VBVZCTDCPYDLDZ-MDWZMJQESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  22
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  66.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  methyl 2-(3,7-dimethylocta-2,6-dienyl)-3,5-dihydroxybenzoate 、 氯甲基甲基醚 在 potassium carbonate 作用下， 以 丙酮 为溶剂， 反应 6.25h， 以99%的产率得到methyl 2-(3,7-dimethylocta-2,6-dienyl)-3,5-bis(methoxymethoxy)benzoate
  参考文献：
  名称：

  A Concise Synthesis of Pawhuskin A

  摘要：

  Pawhuskin A is an isoprenylated stilbene that was isolated from Dalea purpurea and reported to have affinity for the opioid receptor in vitro. It has been synthesized through a convergent sequence that joins a prenylated aldehyde with a geranylated phosphonate in a stereoselective Horner-Wadsworth-Emmons condensation to afford the target E olefin isomer. This synthesis confirms the structure assigned to the natural product and establishes a route that may be used to explore its biological activity and to prepare more active analogues.

  DOI：

  10.1021/np800351c
• 作为产物：
  描述：

  香叶醇 、 3,5-二羟基苯甲酸甲酯 在 三氟化硼乙醚 作用下， 以 1,4-二氧六环 为溶剂， 反应 2.83h， 以35%的产率得到methyl 2-(3,7-dimethylocta-2,6-dienyl)-3,5-dihydroxybenzoate
  参考文献：
  名称：

  A Concise Synthesis of Pawhuskin A

  摘要：

  Pawhuskin A is an isoprenylated stilbene that was isolated from Dalea purpurea and reported to have affinity for the opioid receptor in vitro. It has been synthesized through a convergent sequence that joins a prenylated aldehyde with a geranylated phosphonate in a stereoselective Horner-Wadsworth-Emmons condensation to afford the target E olefin isomer. This synthesis confirms the structure assigned to the natural product and establishes a route that may be used to explore its biological activity and to prepare more active analogues.

  DOI：

  10.1021/np800351c