(E)-methyl 5-(2-acetylphenyl)pent-2-enoate | 1444403-84-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (E)-methyl 5-(2-acetylphenyl)pent-2-enoate
• CAS: 1444403-84-2
• 化学式: C₁₄H₁₆O₃
• 分子量: 232.279
• InChiKey: GVBFNFLSLDIUCN-UXBLZVDNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.55
• 重原子数：
  17.0
• 可旋转键数：
  5.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  43.37
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (E)-methyl 5-(2-acetylphenyl)pent-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42%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：

  4-甲基-1,2-二氢萘 在 臭氧 、 三乙胺 、 lithium chloride 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 9.75h， 生成 (E)-methyl 5-(2-acetylphenyl)pent-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