tert-butyl (2E,4E,6R,7R,9E)-7-hydroxy-4,6,9-trimethyl-12-(trimethylsilyl)dodeca-2,4,9-trien-11-ynoate | 1191072-41-9

• 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: tert-butyl (2E,4E,6R,7R,9E)-7-hydroxy-4,6,9-trimethyl-12-(trimethylsilyl)dodeca-2,4,9-trien-11-ynoate
• CAS: 1191072-41-9
• 化学式: C₂₂H₃₆O₃Si
• 分子量: 376.612
• InChiKey: SHABJUBTWBGACU-NMOFMUGISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.04
• 重原子数：
  26.0
• 可旋转键数：
  6.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  46.53
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  tert-butyl (2E,4E,6R,7R,9E)-7-hydroxy-4,6,9-trimethyl-12-(trimethylsilyl)dodeca-2,4,9-trien-11-ynoate 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 0.25h， 以99%的产率得到tert-butyl (2E,4E,6R,7R,9E)-7-hydroxy-4,6,9-trimethyldodeca-2,4,9-trien-11-ynoate
  参考文献：
  名称：

  Catalytic Asymmetric Synthesis of Palmerolide A via Organoboron Methodology

  摘要：

  A catalytic enantioselective synthesis of the antimelanoma marine natural product (-)-palmerolide A was accomplished using a longest sequence of 21 steps and without resorting to stoichiometric chiral auxiliaries or the chiral pool. The right half was constructed with a new variant of the Claisen-Ireland rearrangement exploiting an alkenylboronate as a masked hydroxyl. The left half featured the first application of a diol.SnCl4-catalyzed enantioselective crotylboration in the context of a complex target. This distinct strategy could the way to the design of simplified analogues of palmerolide.

  DOI：

  10.1021/ja906429c
• 作为产物：
  描述：

  tert-butyl (2E,4E,6R,7R,9E)-7-hydroxy-10-iodo-4,6,9-trimethyldeca-2,4,9-trienoate 、 三甲基乙炔基硅 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 二乙胺 作用下， 反应 2.0h， 以97%的产率得到tert-butyl (2E,4E,6R,7R,9E)-7-hydroxy-4,6,9-trimethyl-12-(trimethylsilyl)dodeca-2,4,9-trien-11-ynoate
  参考文献：
  名称：

  Catalytic Asymmetric Synthesis of Palmerolide A via Organoboron Methodology

  摘要：

  A catalytic enantioselective synthesis of the antimelanoma marine natural product (-)-palmerolide A was accomplished using a longest sequence of 21 steps and without resorting to stoichiometric chiral auxiliaries or the chiral pool. The right half was constructed with a new variant of the Claisen-Ireland rearrangement exploiting an alkenylboronate as a masked hydroxyl. The left half featured the first application of a diol.SnCl4-catalyzed enantioselective crotylboration in the context of a complex target. This distinct strategy could the way to the design of simplified analogues of palmerolide.

  DOI：

  10.1021/ja906429c