tert-butyl[{2-(2E-3,7-dimethyl-2,6-octadienyl)-3,5-bis(methoxymethoxy)benzyl}oxy]dimethylsilane | 1075694-32-4

• 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: tert-butyl[{2-(2E-3,7-dimethyl-2,6-octadienyl)-3,5-bis(methoxymethoxy)benzyl}oxy]dimethylsilane
• 英文别名: tert-butyl-[[2-[(2E)-3,7-dimethylocta-2,6-dienyl]-3,5-bis(methoxymethoxy)phenyl]methoxy]-dimethylsilane
• CAS: 1075694-32-4
• 化学式: C₂₇H₄₆O₅Si
• 分子量: 478.745
• InChiKey: OHPDFPQFQCWVNM-HYARGMPZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.41
• 重原子数：
  33
• 可旋转键数：
  15
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.63
• 拓扑面积：
  46.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  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
• 作为产物：
  描述：

  香叶基溴 、 2-bromo-1-<(tertbutyldimethylsilyl)oxy>-3,5-bis(methoxymethoxy)benzene 在 正丁基锂 、 溴化亚铜二甲硫醚 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 11.5h， 以54%的产率得到tert-butyl[{2-(2E-3,7-dimethyl-2,6-octadienyl)-3,5-bis(methoxymethoxy)benzyl}oxy]dimethylsilane
  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

• 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.