2-(quinolin-4-yl)aniline | 58992-83-9

• 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-(quinolin-4-yl)aniline
• 英文别名: 4-(2-Aminophenyl)chinolin；2-Quinolin-4-ylaniline
• CAS: 58992-83-9
• 化学式: C₁₅H₁₂N₂
• 分子量: 220.274
• InChiKey: RCLKCVIESBQOJV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  38.9
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-(quinolin-4-yl)aniline 在 盐酸 、 氨 、 sodium nitrite 作用下， 以 二氯甲烷 、 水 、 邻二氯苯 、 甲苯 为溶剂， 反应 10.5h， 生成 5-methyl-5H-indolo[2,3-c]quinoline
  参考文献：
  名称：

  Synthesis of the benzo-β-carboline isoneocryptolepine: the missing indoloquinoline isomer in the alkaloid series cryptolepine, neocryptolepine and isocryptolepine

  摘要：

  7H-Indolo[2,3-c]quinoline has been synthesized in two steps via a new approach starting from commercially available 3-bromoquinoline and 2-bromoaniline. The new methodology consists of two consecutive palladium-catalyzed reactions: a selective Buchwald/Hartwig amination followed by an intramolecular Heck-type reaction. Alternatively, the same skeleton has also been prepared via the combination of a Suzuki arylation with an intramolecular nitrene insertion starting front 4-chloroquinotine and [2-[(2-2dimethylpropanoyl)amino]phenyl}boronic acid. Selective methylation of 7H-indolo[2.3-c]quinotine yielded 5-methyl-5H-indolo[2,3c]quinoline (Isoneocryptolepine) which is an interesting new lead compound in the search for new antiplasmodial drugs. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2004.11.073
• 作为产物：
  描述：

  4-氯喹啉 在 四(三苯基膦)钯 硫酸 、 sodium carbonate 作用下， 以 乙二醇二甲醚 、 乙醇 、 水 为溶剂， 反应 44.0h， 生成 2-(quinolin-4-yl)aniline
  参考文献：
  名称：

  Synthesis of the benzo-β-carboline isoneocryptolepine: the missing indoloquinoline isomer in the alkaloid series cryptolepine, neocryptolepine and isocryptolepine

  摘要：

  7H-Indolo[2,3-c]quinoline has been synthesized in two steps via a new approach starting from commercially available 3-bromoquinoline and 2-bromoaniline. The new methodology consists of two consecutive palladium-catalyzed reactions: a selective Buchwald/Hartwig amination followed by an intramolecular Heck-type reaction. Alternatively, the same skeleton has also been prepared via the combination of a Suzuki arylation with an intramolecular nitrene insertion starting front 4-chloroquinotine and [2-[(2-2dimethylpropanoyl)amino]phenyl}boronic acid. Selective methylation of 7H-indolo[2.3-c]quinotine yielded 5-methyl-5H-indolo[2,3c]quinoline (Isoneocryptolepine) which is an interesting new lead compound in the search for new antiplasmodial drugs. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2004.11.073

文献信息

• 10.1021/acs.orglett.4c01613
  作者：Kato, Natsuki、Seki, Yuta、Nanjo, Takeshi、Takemoto, Yoshiji

  DOI：10.1021/acs.orglett.4c01613

  日期：——

  enable the direct reductive transformation of a variety of secondary and tertiary aliphatic bromides. A series of experimental and theoretical results suggested that the D–A molecules promote direct C–Br bond cleavage triggered by the excitation of the complex between the catalyst and the aliphatic bromide and that the alkyl groups significantly contribute to the stabilization of the complex, which

  我们报道了新的基于吡啶的供体-受体（D-A）分子，它能够直接还原转化各种仲和叔脂肪族溴化物。一系列实验和理论结果表明，D-A分子促进了由催化剂和脂肪族溴化物之间的络合物激发引发的直接C-Br键断裂，并且烷基对络合物的稳定有显着贡献，这提高其励磁效率。
• 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.
• Synthesis of the benzo-β-carboline isoneocryptolepine: the missing indoloquinoline isomer in the alkaloid series cryptolepine, neocryptolepine and isocryptolepine
  作者：Steven Hostyn、Bert U.W. Maes、Luc Pieters、Guy L.F. Lemière、Péter Mátyus、György Hajós、Roger A. Dommisse

  DOI：10.1016/j.tet.2004.11.073

  日期：2005.2

  7H-Indolo[2,3-c]quinoline has been synthesized in two steps via a new approach starting from commercially available 3-bromoquinoline and 2-bromoaniline. The new methodology consists of two consecutive palladium-catalyzed reactions: a selective Buchwald/Hartwig amination followed by an intramolecular Heck-type reaction. Alternatively, the same skeleton has also been prepared via the combination of a Suzuki arylation with an intramolecular nitrene insertion starting front 4-chloroquinotine and [2-[(2-2dimethylpropanoyl)amino]phenyl}boronic acid. Selective methylation of 7H-indolo[2.3-c]quinotine yielded 5-methyl-5H-indolo[2,3c]quinoline (Isoneocryptolepine) which is an interesting new lead compound in the search for new antiplasmodial drugs. (C) 2004 Elsevier Ltd. All rights reserved.