(E)-methyl 7-oxo-7-(p-tolyl)hept-2-enoate | 1444403-59-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (E)-methyl 7-oxo-7-(p-tolyl)hept-2-enoate
• 英文别名: methyl (E)-7-(4-methylphenyl)-7-oxohept-2-enoate
• CAS: 1444403-59-1
• 化学式: C₁₅H₁₈O₃
• 分子量: 246.306
• InChiKey: KOXDFSFENQIOIP-FNORWQNLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  18
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 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：

  (E)-methyl 7-oxo-7-(p-tolyl)hept-2-enoate 在 磷酸二苯酯 、 2-苯基苯并噻唑 、 C₃₀H₂₄N₆Ru⁽²⁺⁾*2C₁₆H₆BF₁₂^(1-) 作用下， 以 四氢呋喃 为溶剂， 反应 6.0h， 以71%的产率得到
  参考文献：
  名称：

  Catalytic Ketyl-Olefin Cyclizations Enabled by Proton-Coupled Electron Transfer

  摘要：

  Concerted proton-coupled electron transfer is a key mechanism of substrate activation in biological redox catalysis. However, its applications in organic synthesis remain largely unexplored. Herein, we report the development of a new catalytic protocol for ketyl-olefin coupling and present evidence to support concerted proton-coupled electron transfer being the operative mechanism of ketyl formation. Notably, reaction outcomes were correctly predicted by a simple thermodynamic formalism relating the oxidation potentials and pK(a) values of specific Bronsted acid/reductant combinations to their capacity to act jointly as a formal hydrogen atom donor.

  DOI：

  10.1021/ja404342j
• 作为产物：
  描述：

  对溴甲苯 在 RuCl2(1,3-dimesityl-imidazolidin-2-yl)(PCy3)(=CHPh) 、 magnesium 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 反应 12.75h， 生成 (E)-methyl 7-oxo-7-(p-tolyl)hept-2-enoate
  参考文献：
  名称：

  Catalytic Ketyl-Olefin Cyclizations Enabled by Proton-Coupled Electron Transfer

  摘要：

  Concerted proton-coupled electron transfer is a key mechanism of substrate activation in biological redox catalysis. However, its applications in organic synthesis remain largely unexplored. Herein, we report the development of a new catalytic protocol for ketyl-olefin coupling and present evidence to support concerted proton-coupled electron transfer being the operative mechanism of ketyl formation. Notably, reaction outcomes were correctly predicted by a simple thermodynamic formalism relating the oxidation potentials and pK(a) values of specific Bronsted acid/reductant combinations to their capacity to act jointly as a formal hydrogen atom donor.

  DOI：

  10.1021/ja404342j