2,2-dimethyl-N-[2-(quinolin-4-yl)phenyl]propanamide | 848086-04-4

• 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: 2,2-dimethyl-N-[2-(quinolin-4-yl)phenyl]propanamide
• 英文别名: 2,2-dimethyl-N-(2-quinolin-4-ylphenyl)propanamide
• CAS: 848086-04-4
• 化学式: C₂₀H₂₀N₂O
• 分子量: 304.392
• InChiKey: WKBOOEMVAAHICY-UHFFFAOYSA-N

物化性质

• 沸点：
  476.1±33.0 °C(Predicted)
• 密度：
  1.149±0.06 g/cm3(Predicted)

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：

  2,2-dimethyl-N-[2-(quinolin-4-yl)phenyl]propanamide 在 硫酸 作用下， 以 乙醇 为溶剂， 反应 24.0h， 以89%的产率得到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
• 作为产物：
  描述：

  4-氯喹啉 、 2-(2,2,2-三甲基乙酰氨基)苯硼酸 在 四(三苯基膦)钯 sodium carbonate 作用下， 以 乙二醇二甲醚 、 水 为溶剂， 反应 20.0h， 以96%的产率得到2,2-dimethyl-N-[2-(quinolin-4-yl)phenyl]propanamide
  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

• 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.