2-bromo-4-chlorophenyl cinnamate | 511518-12-0

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: 2-bromo-4-chlorophenyl cinnamate
• 英文别名: (2-Bromo-4-chlorophenyl) 3-phenylprop-2-enoate
• CAS: 511518-12-0
• 化学式: C₁₅H₁₀BrClO₂
• 分子量: 337.6
• InChiKey: OCWIFKFCPHABGO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-bromo-4-chlorophenyl cinnamate 在 氧气 、 三氟乙酸 、 copper dichloride 、 magnesium chloride 作用下， 以 乙腈 为溶剂， 以53 %的产率得到2-bromo-4-chlorophenyl 2-chloro-3-oxo-3-phenylpropanoate
  参考文献：
  名称：

  CuCl ₂ ‐Catalyzed α ‐Chloroketonation of Aromatic Alkenes via Visible‐Light‐Induced LMCT

  摘要：

  AbstractHere we report a copper‐catalyzed protocol for the synthesis of α‐chloroketones from aromatic alkenes including electron‐deficient olefins under visible‐light irradiation. Preliminary mechanistic studies show that the peroxo Cu(II) species is the key intermediate and hydroperoxyl (HOO⋅) and chlorine (Cl⋅) radicals can be generated by ligand‐to‐metal charge transfer (LMCT).

  DOI：

  10.1002/asia.202200954
• 作为产物：
  描述：

  2-溴-4-氟苯酚 、 肉桂酰氯 在 三乙胺 作用下， 以65 %的产率得到2-bromo-4-chlorophenyl cinnamate
  参考文献：
  名称：

  CuCl ₂ ‐Catalyzed α ‐Chloroketonation of Aromatic Alkenes via Visible‐Light‐Induced LMCT

  摘要：

  AbstractHere we report a copper‐catalyzed protocol for the synthesis of α‐chloroketones from aromatic alkenes including electron‐deficient olefins under visible‐light irradiation. Preliminary mechanistic studies show that the peroxo Cu(II) species is the key intermediate and hydroperoxyl (HOO⋅) and chlorine (Cl⋅) radicals can be generated by ligand‐to‐metal charge transfer (LMCT).

  DOI：

  10.1002/asia.202200954

文献信息

• CuCl ₂ ‐Catalyzed <i>α</i> ‐Chloroketonation of Aromatic Alkenes via Visible‐Light‐Induced LMCT
  作者：Xing‐Xian He、Huan‐Huan Chang、Ying‐Xue Zhao、Xiang‐Jie Li、Sheng‐An Liu、Zhong‐Lin Zang、Cheng‐He Zhou、Gui‐Xin Cai

  DOI：10.1002/asia.202200954

  日期：2023.1.3

  AbstractHere we report a copper‐catalyzed protocol for the synthesis of α‐chloroketones from aromatic alkenes including electron‐deficient olefins under visible‐light irradiation. Preliminary mechanistic studies show that the peroxo Cu(II) species is the key intermediate and hydroperoxyl (HOO⋅) and chlorine (Cl⋅) radicals can be generated by ligand‐to‐metal charge transfer (LMCT).