ethyl-(E)-5,5-dimethyl-6-oxo-hept-2-enoate | 446251-26-9

• 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: ethyl-(E)-5,5-dimethyl-6-oxo-hept-2-enoate
• 英文别名: ethyl (E)-5,5-dimethyl-6-oxohept-2-enoate
• CAS: 446251-26-9
• 化学式: C₁₁H₁₈O₃
• 分子量: 198.262
• InChiKey: CIVYOCGFDQMMSG-VOTSOKGWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  14
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.64
• 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)-5,5-dimethyl-6-oxo-hept-2-enoate 在 甲醇 、 lithium aluminium tetrahydride 、 samarium diiodide 作用下， 以 四氢呋喃 、 吡啶 为溶剂， 反应 22.0h， 生成 2-hydroxy-2,3,3-trimethyl-cyclopentylmethyl-p-nitro benzoate
  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：

  Alpha,Alpha-二甲基-γ-丁内酯 在 草酰氯 、 二异丁基氢化铝 、 二甲基亚砜 、 三乙胺 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 为溶剂， 反应 34.5h， 生成 ethyl-(E)-5,5-dimethyl-6-oxo-hept-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

文献信息

• Samarium(II)-Mediated Reactions of γ,δ-Unsaturated Ketones. Cyclization and Fragmentation Processes
  作者：Thomas K. Hutton、Kenneth Muir、David J. Procter

  DOI：10.1021/ol0260472

  日期：2002.7.1

  [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.