(Z)-3-chloro-2-((5-oxotetrahydrofuran-2-yl)methyl)-3-phenylacrylamide | 1620886-92-1

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮
• 英文名称: (Z)-3-chloro-2-((5-oxotetrahydrofuran-2-yl)methyl)-3-phenylacrylamide
• CAS: 1620886-92-1
• 化学式: C₁₄H₁₄ClNO₃
• 分子量: 279.723
• InChiKey: HGCCGLBMOWQBBP-QBFSEMIESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.22
• 重原子数：
  19.0
• 可旋转键数：
  4.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  69.39
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为产物：
  描述：

  3-苯基丙-2-炔酰胺 、 (Z)-3-chloro-3-phenyl-2-((tetrahydrofuran-2-yl)methyl)acrylamide 在 copper chloride dihydrate 、 palladium diacetate 作用下， 以 乙腈 为溶剂， 反应 12.0h， 以79%的产率得到(Z)-3-chloro-2-((5-oxotetrahydrofuran-2-yl)methyl)-3-phenylacrylamide
  参考文献：
  名称：

  Nucleopalladation-Initiated Oxyalkenylation of Alkenes: A Strategy To Construct Functionalized Oxygenated Heterocycles

  摘要：

  A convenient and efficient approach to construct functionalized oxygen heterocycles, i.e., tetrahydrofurans, tetrahydropyrans, and γ-lactones, has been reported. This process successfully provides a route to construct derivatives of naturally occurring biologically active tetrahydrofurans, especially ones with spirocyclic structure. Highly regio- and stereoselective nucleopalladation of alkynes initiates the cross-coupling between alkynamides and alkenes to give the olefin oxyalkenylation products in good to excellent yields. The hydroxyl group in the olefins cooperates with the amide in alkynamides to promote the cyclization by suppressing the β-H elimination.

  DOI：

  10.1021/jo501317v