ethyl-(E)-6-cyclopropyl-5,5-dimethyl-6-oxo-hex-2-enoate | 446251-33-8

• 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)-6-cyclopropyl-5,5-dimethyl-6-oxo-hex-2-enoate
• 英文别名: ethyl (E)-6-cyclopropyl-5,5-dimethyl-6-oxohex-2-enoate
• CAS: 446251-33-8
• 化学式: C₁₃H₂₀O₃
• 分子量: 224.3
• InChiKey: XZDGIPXDFUZUAF-AATRIKPKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  16
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  ethyl-(E)-6-cyclopropyl-5,5-dimethyl-6-oxo-hex-2-enoate 在 甲醇 、 samarium diiodide 作用下， 以 四氢呋喃 为溶剂， 反应 4.0h， 以42%的产率得到ethyl-6-cyclopropyl-5,5-dimethyl-6-oxo-hexanoate
  参考文献：
  名称：

  Samarium(II)-Mediated Reactions of γ,δ-Unsaturated Ketones. Cyclization and Fragmentation Processes

  摘要：

  [GRAPHICS]On treatment with samarium(II) iodide, gamma,delta-unsaturated ketones undergo very different processes depending upon the nature of the reaction conditions. Employing samarium(II) iodide and MeOH, functionalized syn-cyclopentanol products are obtained stereoselectively. Mechanistic studies suggest that this cyclization occurs via a sequential reduction/intramolecular aldol reaction. With samarium(II) iodide and HMPA, products of a 4-exo-trig cyclization and of an interesting fragmentation reaction are observed.

  DOI：

  10.1021/ol0260472
• 作为产物：
  描述：

  2-羟基-3,3-二甲基四氢呋喃 在 草酰氯 、 二甲基亚砜 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 16.0h， 生成 ethyl-(E)-6-cyclopropyl-5,5-dimethyl-6-oxo-hex-2-enoate
  参考文献：
  名称：

  Samarium(II)-Mediated Reactions of γ,δ-Unsaturated Ketones. Cyclization and Fragmentation Processes

  摘要：

  [GRAPHICS]On treatment with samarium(II) iodide, gamma,delta-unsaturated ketones undergo very different processes depending upon the nature of the reaction conditions. Employing samarium(II) iodide and MeOH, functionalized syn-cyclopentanol products are obtained stereoselectively. Mechanistic studies suggest that this cyclization occurs via a sequential reduction/intramolecular aldol reaction. With samarium(II) iodide and HMPA, products of a 4-exo-trig cyclization and of an interesting fragmentation reaction are observed.

  DOI：

  10.1021/ol0260472