(E)-butyl 3-(4-oxo-2-phenyl-4H-chromen-3-yl)acrylate | 1321627-99-9

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 黄酮类化合物
• 英文名称: (E)-butyl 3-(4-oxo-2-phenyl-4H-chromen-3-yl)acrylate
• 英文别名: butyl (E)-3-(4-oxo-2-phenylchromen-3-yl)prop-2-enoate
• CAS: 1321627-99-9
• 化学式: C₂₂H₂₀O₄
• 分子量: 348.398
• InChiKey: UJGWWEZRWBNMEA-BUHFOSPRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  26
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  黄酮 、 丙烯酸丁酯 在 copper diacetate 、 palladium diacetate 、 silver carbonate 、 三甲基乙酸 作用下， 反应 18.0h， 以52%的产率得到(E)-butyl 3-(4-oxo-2-phenyl-4H-chromen-3-yl)acrylate
  参考文献：
  名称：

  Palladium(II)-Catalyzed Direct Intermolecular Alkenylation of Chromones

  摘要：

  A new efficient method for the direct alkenylation of chromones via a palladium(II)-catalyzed C-H functionalization reaction was developed. The use of pivalic acid with Cu(OAc)(3)/Ag2CO3 provided superior reactivity in the cross-coupling of chromones with alkene partners. This approach represents a significant advance over the existing two-step method and afforded various 3-vinylchromone derivatives, which are privileged structures in many biologically active compounds and versatile synthetic building blocks.

  DOI：

  10.1021/ol2018278

文献信息

• Palladium-Catalyzed Dehydrogenation/Oxidative Cross-Coupling Sequence of β-Heteroatom-Substituted Ketones
  作者：Youngtaek Moon、Daeil Kwon、Sungwoo Hong

  DOI：10.1002/anie.201206610

  日期：2012.11.5

  Concise and selective: The title one‐pot sequence allows formation of the enone functionality and subsequent cross‐coupling. The process provides access to highly functionalized cyclic enolones and enaminones from readily accessible β‐heteroatom‐substituted cyclic ketones.

  简洁，选择性：标题一锅法序列可形成烯酮功能并随后进行交叉偶联。该方法提供了从容易获得的β-杂原子取代的环酮中获得高度官能化的环状烯酮和烯胺酮的途径。
• Palladium(II)-Catalyzed Direct Intermolecular Alkenylation of Chromones
  作者：Donghee Kim、Sungwoo Hong

  DOI：10.1021/ol2018278

  日期：2011.8.19

  A new efficient method for the direct alkenylation of chromones via a palladium(II)-catalyzed C-H functionalization reaction was developed. The use of pivalic acid with Cu(OAc)(3)/Ag2CO3 provided superior reactivity in the cross-coupling of chromones with alkene partners. This approach represents a significant advance over the existing two-step method and afforded various 3-vinylchromone derivatives, which are privileged structures in many biologically active compounds and versatile synthetic building blocks.