N-pyvaloyl-2-(2'-anilino)quinoline | 250593-10-3

• 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: N-pyvaloyl-2-(2'-anilino)quinoline
• 英文别名: N-(2-(quinolin-2-yl)phenyl)pivalamide；2,2-dimethyl-N-(2-quinolin-2-ylphenyl)propanamide
• CAS: 250593-10-3
• 化学式: C₂₀H₂₀N₂O
• 分子量: 304.392
• InChiKey: KSMGRIHUXSIUKW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  23
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  42
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-pyvaloyl-2-(2'-anilino)quinoline 在 盐酸 、 硫酸 、 sodium nitrite 作用下， 以 水 、 邻二氯苯 为溶剂， 反应 9.0h， 生成 indazolo[2,3-a]quinoline
  参考文献：
  名称：

  An Alternative Synthesis of Quindoline and one of its Closely Related Derivatives

  摘要：

  The alkaloid Quindoline (13) and one of its tetracyclic isomer indazolo[2,3-a]quinoline (8) have been synthesised utilising the Pd(0)-catalysed cross-coupling reaction of pivaloylamino phenylboronic acid (2) with substituted quinolines.

  DOI：

  10.1080/00397919908085916
• 作为产物：
  描述：

  邻氨基苯硼酸盐酸盐 在 (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride 、 四(三苯基膦)钯 、 双氧水 、 caesium carbonate 、 1,3-bis(2,4,6-trimethylphenyl)-imidazolium 作用下， 以 乙二醇二甲醚 、 水 为溶剂， 反应 16.0h， 生成 N-pyvaloyl-2-(2'-anilino)quinoline
  参考文献：
  名称：

  Mapping the reactivity of the quinoline ring-system – Synthesis of the tetracyclic ring-system of isocryptolepine and regioisomers

  摘要：

  Bromoquinolines (2-bromoquinoline - 8-bromoquinoline and 5-bromo-3-methoxyquinoline) and 2-aminophenylboronic acid hydrochloride were subjected to Suzuki-Miyaura cross-coupling conditions resulting in formation of the desired biaryl systems in good yields. The resulting biaryls were then subjected to palladium catalyzed C-H activation/C-N bond formation utilizing PdCl2(dppf). The reactions revealed large differences in reactivity depending on the attachment point for the 2-aminophenyl group on the quinoline. The variation in the reactivity was rationalized based on the electron distribution around the quinoline ring-system. (C) 2019 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2019.04.026

文献信息

• Mapping the reactivity of the quinoline ring-system – Synthesis of the tetracyclic ring-system of isocryptolepine and regioisomers
  作者：Katja S. Håheim、Ida T. Urdal Helgeland、Emil Lindbäck、Magne O. Sydnes

  DOI：10.1016/j.tet.2019.04.026

  日期：2019.5

  Bromoquinolines (2-bromoquinoline - 8-bromoquinoline and 5-bromo-3-methoxyquinoline) and 2-aminophenylboronic acid hydrochloride were subjected to Suzuki-Miyaura cross-coupling conditions resulting in formation of the desired biaryl systems in good yields. The resulting biaryls were then subjected to palladium catalyzed C-H activation/C-N bond formation utilizing PdCl2(dppf). The reactions revealed large differences in reactivity depending on the attachment point for the 2-aminophenyl group on the quinoline. The variation in the reactivity was rationalized based on the electron distribution around the quinoline ring-system. (C) 2019 Elsevier Ltd. All rights reserved.
• An Alternative Synthesis of Quindoline and one of its Closely Related Derivatives
  作者：D. Csányi、G. Timári、Gy. Hajós

  DOI：10.1080/00397919908085916

  日期：1999.11

  The alkaloid Quindoline (13) and one of its tetracyclic isomer indazolo[2,3-a]quinoline (8) have been synthesised utilising the Pd(0)-catalysed cross-coupling reaction of pivaloylamino phenylboronic acid (2) with substituted quinolines.