(Z)-N-benzyl-3-chloro-3-phenyl-2-((tetrahydrofuran-2-yl)methyl)acrylamide | 1620886-80-7

• 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: (Z)-N-benzyl-3-chloro-3-phenyl-2-((tetrahydrofuran-2-yl)methyl)acrylamide
• 英文别名: (Z)-N-benzyl-3-chloro-2-(oxolan-2-ylmethyl)-3-phenylprop-2-enamide
• CAS: 1620886-80-7
• 化学式: C₂₁H₂₂ClNO₂
• 分子量: 355.864
• InChiKey: FAPCSRPSWUPMTQ-VXPUYCOJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  25
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  38.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  4-戊烯-1-醇 、 N-benzyl-3-phenylpropiolamide 在 copper chloride dihydrate 、 palladium diacetate 作用下， 以 乙腈 为溶剂， 反应 12.0h， 以84%的产率得到(Z)-N-benzyl-3-chloro-3-phenyl-2-((tetrahydrofuran-2-yl)methyl)acrylamide
  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

文献信息

• Nucleopalladation-Initiated Oxyalkenylation of Alkenes: A Strategy To Construct Functionalized Oxygenated Heterocycles
  作者：Liangbin Huang、Qian Wang、Wanqing Wu、Huanfeng Jiang

  DOI：10.1021/jo501317v

  日期：2014.8.15

  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.