(Z)-N-(quinolin-8-yl)-3-(thiophen-2-yl)acrylamide

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: (Z)-N-(quinolin-8-yl)-3-(thiophen-2-yl)acrylamide
• 英文别名: (Z)-N-quinolin-8-yl-3-thiophen-2-ylprop-2-enamide
• 化学式: C₁₆H₁₂N₂OS
• 分子量: 280.35
• InChiKey: OMJUQAZFVWFSQJ-HJWRWDBZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  70.2
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2-碘噻吩 、 N-(quinolin-8-yl)acrylamide 在 silver(I) acetate 、 palladium diacetate 作用下， 以 甲苯 为溶剂， 以60%的产率得到
  参考文献：
  名称：

  Pd(OAc)₂-Catalyzed, AgOAc-Promoted Z Selective Directed β-Arylation of Acrylamide Systems and Stereoselective Construction of Z-Cinnamamide Scaffolds

  摘要：

  A Pd(OAc)(2)-catalyzed, AgOAc-promoted and bidentate ligand-directed Z selective C-H activation, followed by the beta-arylation of the C(sp(2))-H bond of N-(quinolin-8-yl)acrylamide systems with aryl- and heteroaryl iodides, and a contemporary method for the construction of various Z-cinnamamides and beta,beta-diarylated acrylamides are reported. A plausible reaction mechanism comprising the bidentate ligand-aided, chelation-based C-H functionalization was proposed for the observed Z selective beta-arylation of N-(quinolin-8-yl)acrylamide systems.

  DOI：

  10.1021/acs.joc.5b02264

文献信息

• Pd(OAc)₂-Catalyzed, AgOAc-Promoted <i>Z</i> Selective Directed β-Arylation of Acrylamide Systems and Stereoselective Construction of <i>Z</i>-Cinnamamide Scaffolds
  作者：Ramarao Parella、Srinivasarao Arulananda Babu

  DOI：10.1021/acs.joc.5b02264

  日期：2015.12.18

  A Pd(OAc)(2)-catalyzed, AgOAc-promoted and bidentate ligand-directed Z selective C-H activation, followed by the beta-arylation of the C(sp(2))-H bond of N-(quinolin-8-yl)acrylamide systems with aryl- and heteroaryl iodides, and a contemporary method for the construction of various Z-cinnamamides and beta,beta-diarylated acrylamides are reported. A plausible reaction mechanism comprising the bidentate ligand-aided, chelation-based C-H functionalization was proposed for the observed Z selective beta-arylation of N-(quinolin-8-yl)acrylamide systems.