(Z)-N-(quinolin-8-yl)cinnamamide

• 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-(quinolin-8-yl)cinnamamide
• 英文别名: (Z)-3-phenyl-N-(quinolin-8-yl)acrylamide；N-(quinolin-8-yl)cinnamamide；(Z)-3-phenyl-N-quinolin-8-ylprop-2-enamide
• 化学式: C₁₈H₁₄N₂O
• 分子量: 274.322
• InChiKey: CTPSLLCFINSULA-QXMHVHEDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  21
• 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：
  42
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  N-(quinolin-8-yl)acrylamide 、 碘苯 在 silver(I) acetate 、 palladium diacetate 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 24.0h， 以44%的产率得到(Z)-N-(quinolin-8-yl)cinnamamide
  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

• Iron-Catalyzed C(sp²)–H Bond Functionalization with Organoboron Compounds
  作者：Rui Shang、Laurean Ilies、Sobi Asako、Eiichi Nakamura

  DOI：10.1021/ja5070763

  日期：2014.10.15

  We report here that an iron-catalyzed directed CH functionalization reaction allows the coupling of a variety of aromatic, heteroaromatic, and olefinic substrates with alkenyl and aryl boron compounds under mild oxidative conditions. We rationalize these results by the involvement of an organoiron(III) reactive intermediate that is responsible for the CH bond-activation process. A zinc salt is crucial to promote the transfer of the organic group from the boron atom to the iron(III) atom.