[2-(3,7-dimethylocta-2,6-dienyl)-3,5-bis(methoxymethoxy)phenyl]methanol | 1075694-34-6

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: [2-(3,7-dimethylocta-2,6-dienyl)-3,5-bis(methoxymethoxy)phenyl]methanol
• 英文别名: [2-[(2E)-3,7-dimethylocta-2,6-dienyl]-3,5-bis(methoxymethoxy)phenyl]methanol
• CAS: 1075694-34-6
• 化学式: C₂₁H₃₂O₅
• 分子量: 364.482
• InChiKey: NIUVBUZBALWPIG-RQZCQDPDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  26
• 可旋转键数：
  12
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  57.2
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  [2-(3,7-dimethylocta-2,6-dienyl)-3,5-bis(methoxymethoxy)phenyl]methanol 在 manganese(IV) oxide 、 双(三甲基硅烷基)氨基钾 、 对甲苯磺酸 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 甲苯 为溶剂， 反应 28.0h， 生成 2-geranyl-3,5,3′,4′-tetrahydroxy-(E)-stilbene
  参考文献：
  名称：

  Stilbenes as κ-Selective, Non-nitrogenous Opioid Receptor Antagonists

  摘要：

  The natural stilbene pawhuskin A has been shown to function as an opioid receptor antagonist, with preferential binding to the kappa receptor. This finding encouraged assembly of a set of analogues to probe the importance of key structural features. Assays on these compounds determined that one (compound 29) shows potent opioid receptor binding activity and significantly improved selectivity for the kappa receptor. These studies begin to illuminate the structural features of these non-nitrogenous opioid, receptor antagonists that are required for activity.

  DOI：

  10.1021/np4009046
• 作为产物：
  描述：

  tert-butyl[{2-(2E-3,7-dimethyl-2,6-octadienyl)-3,5-bis(methoxymethoxy)benzyl}oxy]dimethylsilane 在 四丁基氟化铵 作用下， 以78%的产率得到[2-(3,7-dimethylocta-2,6-dienyl)-3,5-bis(methoxymethoxy)phenyl]methanol
  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

文献信息

• Stilbenes as κ-Selective, Non-nitrogenous Opioid Receptor Antagonists
  作者：Alyssa M. Hartung、John A. Beutler、Hernán A. Navarro、David F. Wiemer、Jeffrey D. Neighbors

  DOI：10.1021/np4009046

  日期：2014.2.28

  The natural stilbene pawhuskin A has been shown to function as an opioid receptor antagonist, with preferential binding to the kappa receptor. This finding encouraged assembly of a set of analogues to probe the importance of key structural features. Assays on these compounds determined that one (compound 29) shows potent opioid receptor binding activity and significantly improved selectivity for the kappa receptor. These studies begin to illuminate the structural features of these non-nitrogenous opioid, receptor antagonists that are required for activity.
• A Concise Synthesis of Pawhuskin A
  作者：Jeffrey D. Neighbors、Matthew J. Buller、Kelly D. Boss、David F. Wiemer

  DOI：10.1021/np800351c

  日期：2008.12.1

  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.