2-p-tolyl-3-methyl-4-phenyl-6-nitroquinoline | 1353040-76-2

• 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: 2-p-tolyl-3-methyl-4-phenyl-6-nitroquinoline
• 英文别名: 2-p-tolyl-3-methyl-6-nitro-4-phenylquinoline；3-Methyl-2-(4-methylphenyl)-6-nitro-4-phenylquinoline
• CAS: 1353040-76-2
• 化学式: C₂₃H₁₈N₂O₂
• 分子量: 354.408
• InChiKey: IARFSQXYABQMOL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6
• 重原子数：
  27
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  58.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  4-硝基苯胺 在 三氟甲磺酸 、 双三氟甲烷磺酰亚胺银盐 作用下， 以 甲苯 为溶剂， 反应 24.17h， 生成 2-p-tolyl-3-methyl-4-phenyl-6-nitroquinoline
  参考文献：
  名称：

  Silver-Mediated C–H Activation: Oxidative Coupling/Cyclization of N-Arylimines and Alkynes for the Synthesis of Quinolines

  摘要：

  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.

  DOI：

  10.1021/jo202087j

文献信息

• 一种利用芳香胺、芳香醛、酮合成喹啉衍生物 的方法
  申请人：南阳师范学院

  公开号：CN105175328B

  公开（公告）日：2017-12-19

  本发明提供了一种利用芳香胺、芳香醛、酮合成喹啉衍生物的方法，属于喹啉衍生物的合成技术领域。一种利用芳香胺、芳香醛、酮合成喹啉衍生物的方法，在三氟甲磺酸银和三氟甲磺酸的存在下，由芳香胺化合物、芳香醛化合物和酮化合物反应合成喹啉衍生物，反应通式如下：。与现有技术相比，本方法不仅能够适用于大量的官能团，而且操作简单、产率高，产物结构单一，便于分离和提纯、安全廉价、污染小。
• Silver-catalyzed one-step synthesis of multiply substituted quinolines
  作者：Xuefeng Xu、Wenmin Liu、Zhiqiang Wang、Yuquan Feng、Yanlei Yan、Xu Zhang

  DOI：10.1016/j.tetlet.2015.12.028

  日期：2016.1

  A silver-catalyzed formation of C-C bond for the construction of a series of polysubstituted quinolines from arylamines, aldehydes, and ketones or arylamines and 1,3-diketones has been developed. The transformation is effective for a broad range of substrates, thus enabling the expansion of constituent architectures on the heterocyclic framework. This use of a single catalytic system to mediate chemical transformations in a synthetic operation is important for the development of new atom-economic strategies and this strategy is efficient in building complex structures from simple starting materials in an environmentally benign fashion. (C) 2015 Elsevier Ltd. All rights reserved.
• 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.