ethyl 2-p-tolyl-6-methylquinoline-3-carboxylate | 1353040-80-8

• 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: ethyl 2-p-tolyl-6-methylquinoline-3-carboxylate
• 英文别名: Ethyl 6-methyl-2-(4-methylphenyl)quinoline-3-carboxylate
• CAS: 1353040-80-8
• 化学式: C₂₀H₁₉NO₂
• 分子量: 305.376
• InChiKey: NTFXTVFQNKRGIV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  39.2
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  对甲基苯甲醛 在 三氟甲磺酸 、 氧气 、 silver trifluoromethanesulfonate 作用下， 以 甲苯 为溶剂， 反应 12.08h， 生成 ethyl 2-p-tolyl-6-methylquinoline-3-carboxylate
  参考文献：
  名称：

  银催化的三组分方法以苯胺、醛和醇为原料制备喹啉

  摘要：

  已经开发出银催化连续形成两个 C-C 键，用于在温和条件下从苯胺、醛和醇构建一系列多取代喹啉。该转变对广泛的底物有效，包括脂肪醇、芳基烷醇、环烷醇和乙二醇，从而允许扩展杂环骨架的构成结构。

  DOI：

  10.1055/s-0035-1561916

文献信息

• Silver-Mediated C–H Activation: Oxidative Coupling/Cyclization of <i>N</i>-Arylimines and Alkynes for the Synthesis of Quinolines
  作者：Xu Zhang、Baoqing Liu、Xin Shu、Yang Gao、Haipeng Lv、Jin Zhu

  DOI：10.1021/jo202087j

  日期：2012.1.6

  A silver-mediated tandem protocol for the synthesis of quinolines involving the oxidative coupling/cyclization of N-arylimines and alkynes has been developed. We demonstrated that scenario-dependent metalation could occur either at the ortho C-H bond of an N-arylimine through protonation-driven enhancement of acidity or at the terminal C-H bond of an alkyne by virtue of the carbophilic pi-acidity of silver. The diverse set of mechanistic manifolds implemented with a single type of experimental protocol points toward the importance of stringent reactivity analysis of each individual potentially reactive molecular site. Importantly, the direct arene C H bond activation provides a unique and distinct mechanistic handle for the expansion of reactivity paradigms for silver. As expected, the protocol allows for the incorporation of both internal and terminal alkynes into the products, and in addition, both electron-withdrawing and -donating groups are tolerated on N-arylimines, thus enabling the vast expansion of substituent architectures on quinoline framework. Further, an intriguing phenomenon of structural isomerization and chemical bond cleavage has been observed for aliphatic internal alkynes.
• Silver-Catalyzed Three-Component Approach to Quinolines Starting from Anilines, Aldehydes, and Alcohols
  作者：Xu Zhang、Zhiqiang Wang、Wenmin Liu、Ruixue Sun、Xuefeng Xu、Yanlei Yan

  DOI：10.1055/s-0035-1561916

  日期：——

  A silver-catalyzed sequential formation of two C–C bonds for the construction of a series of polysubstituted quinolines from anilines, aldehydes, and alcohols under mild conditions has been developed. The transformation is effective for a broad range of substrates, including aliphatic alcohols, arylalkanols, cycloalkanols, and ethylene glycol, thereby permitting the expansion of the constituent architectures

  已经开发出银催化连续形成两个 C-C 键，用于在温和条件下从苯胺、醛和醇构建一系列多取代喹啉。该转变对广泛的底物有效，包括脂肪醇、芳基烷醇、环烷醇和乙二醇，从而允许扩展杂环骨架的构成结构。