ethyl (E)-2,7-dimethyl-4,6-octadienoate | 134486-05-8

• 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: ethyl (E)-2,7-dimethyl-4,6-octadienoate
• 英文别名: ethyl (Z)-2,7-dimethyl-4,6-octadienoate；ethyl 2,7-dimethyl-4,6-octadienoate
• CAS: 134486-05-8；134486-18-3
• 化学式: C₁₂H₂₀O₂
• 分子量: 196.29
• InChiKey: BNCRVWPBPHIWPJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  14.0
• 可旋转键数：
  5.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  26.3
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  ethyl (E)-2,7-dimethyl-4,6-octadienoate 在 二异丁基氢化铝 作用下， 以 正己烷 为溶剂， 反应 0.5h， 以94%的产率得到2,7-dimethyl-4,6-octadien-1-ol
  参考文献：
  名称：

  Synthesis of furanoid terpenes via an efficient palladium-catalyzed cyclization of 4,6-dienols

  摘要：

  The total syntheses of marmelo oxides A and B and a terpene alcohol found in peppermint oil are described. The key steps in these syntheses are the regioselective palladium-catalyzed allylic substitution of 4 and 11 to 6a and 12, respectively, and the regioselective palladium-catalyzed cyclization of 8 and 14 to 9a, 9b, and 15, respectively. The relative stereochemistry of marmelo oxides A and B was established by NOE measurements.

  DOI：

  10.1021/jo00018a027
• 作为产物：
  描述：

  (E)-2-methyl-3,5-hexadien-2-ol 在 palladium diacetate 4-二甲氨基吡啶 、 三丁基膦 、 氰化钠 、 水 、 sodium hydride 、 三乙胺 作用下， 以 二甲基亚砜 为溶剂， 反应 26.0h， 生成 ethyl (E)-2,7-dimethyl-4,6-octadienoate
  参考文献：
  名称：

  Synthesis of furanoid terpenes via an efficient palladium-catalyzed cyclization of 4,6-dienols

  摘要：

  The total syntheses of marmelo oxides A and B and a terpene alcohol found in peppermint oil are described. The key steps in these syntheses are the regioselective palladium-catalyzed allylic substitution of 4 and 11 to 6a and 12, respectively, and the regioselective palladium-catalyzed cyclization of 8 and 14 to 9a, 9b, and 15, respectively. The relative stereochemistry of marmelo oxides A and B was established by NOE measurements.

  DOI：

  10.1021/jo00018a027

文献信息

• Synthesis of furanoid terpenes via an efficient palladium-catalyzed cyclization of 4,6-dienols
  作者：Pher G. Andersson、Jan E. Baeckvall

  DOI：10.1021/jo00018a027

  日期：1991.8

  The total syntheses of marmelo oxides A and B and a terpene alcohol found in peppermint oil are described. The key steps in these syntheses are the regioselective palladium-catalyzed allylic substitution of 4 and 11 to 6a and 12, respectively, and the regioselective palladium-catalyzed cyclization of 8 and 14 to 9a, 9b, and 15, respectively. The relative stereochemistry of marmelo oxides A and B was established by NOE measurements.