(E)-ethyl 2,5,5-trimethyloct-2-en-7-ynoate | 1448521-04-7

• 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: (E)-ethyl 2,5,5-trimethyloct-2-en-7-ynoate
• 英文别名: ethyl (E)-2,5,5-trimethyloct-2-en-7-ynoate
• CAS: 1448521-04-7
• 化学式: C₁₃H₂₀O₂
• 分子量: 208.301
• InChiKey: OJZXOTIPHQQEOF-DHZHZOJOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  15
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (E)-ethyl 2,5,5-trimethyloct-2-en-7-ynoate 在 二异丁基氢化铝 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 0.83h， 以100%的产率得到(E)-2,5,5-trimethyloct-2-en-7-yn-1-ol
  参考文献：
  名称：

  Synthesis of High-Value 1,6-Enynes by Tandem Fragmentation/Olefination

  摘要：

  A tandem process provides high-value 1,6-enynes that are otherwise difficult to prepare. Two base-mediated reactions-fragmentation and olefination-are executed in a coordinated manner that is overall more efficient than either reaction on its own. The 1,6-enynes can be strategically employed in conjunction with carbocyclization to deliver important targets, as noted for reported syntheses of hirsutene and illudol.

  DOI：

  10.1021/ol401839e
• 作为产物：
  描述：

  5,5-dimethyl-3-trifluoromethylsulfonyloxycyclohex-2-en-1-one 在 二异丁基氢化铝 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 正己烷 、 甲苯 为溶剂， 反应 3.66h， 生成 (E)-ethyl 2,5,5-trimethyloct-2-en-7-ynoate 、 (Z)-ethyl 2,5,5-trimethyloct-2-en-7-ynoate
  参考文献：
  名称：

  Synthesis of High-Value 1,6-Enynes by Tandem Fragmentation/Olefination

  摘要：

  A tandem process provides high-value 1,6-enynes that are otherwise difficult to prepare. Two base-mediated reactions-fragmentation and olefination-are executed in a coordinated manner that is overall more efficient than either reaction on its own. The 1,6-enynes can be strategically employed in conjunction with carbocyclization to deliver important targets, as noted for reported syntheses of hirsutene and illudol.

  DOI：

  10.1021/ol401839e

文献信息

• A Total Synthesis of (±)-Ceratopicanol via Palladium Catalyzed Reductive Cyclization
  作者：Rira Kim、Sanghyeon Lee、Jaeyeon Lee、Hee-Yoon Lee

  DOI：10.1002/ejoc.202000769

  日期：2020.8.23

  An efficient total synthesis of ceratopicanol was achieved through successive Pd catalyzed reductive cycloaddition and cyclization reactions. The Pd mediated cyclization reaction to form a triquinane structure demonstrated that a small structural difference changed the reaction pathway either to form different structures or reduced non‐cyclized product depending on the reaction conditions.

  通过连续的Pd催化的还原性环加成反应和环化反应，实现了高效的全氟辛烷醇合成。由Pd介导的环化反应形成三structure烷结构表明，微小的结构差异会根据反应条件改变反应路径以形成不同的结构或还原未环化的产物。
• Synthesis of High-Value 1,6-Enynes by Tandem Fragmentation/Olefination
  作者：Tung T. Hoang、Gregory B. Dudley

  DOI：10.1021/ol401839e

  日期：2013.8.2

  A tandem process provides high-value 1,6-enynes that are otherwise difficult to prepare. Two base-mediated reactions-fragmentation and olefination-are executed in a coordinated manner that is overall more efficient than either reaction on its own. The 1,6-enynes can be strategically employed in conjunction with carbocyclization to deliver important targets, as noted for reported syntheses of hirsutene and illudol.