4-(tert-butyldimethylsilyl)methyl-6-trifluoromethyl-2-phenylquinoline

• 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: 4-(tert-butyldimethylsilyl)methyl-6-trifluoromethyl-2-phenylquinoline
• 英文别名: Tert-butyl-dimethyl-[[2-phenyl-6-(trifluoromethyl)quinolin-4-yl]methyl]silane；tert-butyl-dimethyl-[[2-phenyl-6-(trifluoromethyl)quinolin-4-yl]methyl]silane
• 化学式: C₂₃H₂₆F₃NSi
• 分子量: 401.547
• InChiKey: ADPFDPZXMGNLEB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.51
• 重原子数：
  28
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  12.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  烯丙基(叔丁基)二甲基硅 、 (E)-1-phenyl-N-(4-(trifluoromethyl)phenyl)methanimine 在 triflic imide 作用下， 以 甲苯 为溶剂， 反应 12.0h， 以39%的产率得到4-(tert-butyldimethylsilyl)methyl-6-trifluoromethyl-2-phenylquinoline
  参考文献：
  名称：

  Cascade and one-pot processes providing substituted quinolines from aldimines and allylsilanes: auto-tandem catalysis of triflic imide

  摘要：

  We have demonstrated cascade and one-pot reactions, which constitute inverse electron demand hetero-Diels-Alder reaction and oxidative aromatization, to provide substituted quinolines to form aryl aldimines and allylsilanes. The cascade process involves an auto-tandem catalysis; Tf2NH activates these mechanistically distinct reactions. We have found that a multicomponent process starting from aniline, aldehyde, and allylsilane is also available. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2007.05.032

文献信息

• Auto-Tandem Catalysis in the Synthesis of Substituted Quinolines from Aldimines and Electron-Rich Olefins: Cascade Povarov−Hydrogen-Transfer Reaction
  作者：Naoya Shindoh、Hidetoshi Tokuyama、Yoshiji Takemoto、Kiyosei Takasu

  DOI：10.1021/jo8009243

  日期：2008.10.3

  hetero-Diels-Alder reaction (Povarov reaction) and hydrogen-transfer process. The reaction of electron-rich olefins and excess amount of imines in the presence of acid catalysts under appropriate conditions affords substituted quinolines in a single operation. In the cascade process, the catalysts, such as Tf2NH, TfOH, and Lewis acids, catalyze two mechanistically distinct reactions (auto-tandem catalysis)

  我们证明了催化级联反电子需求杂Diels-Alder反应（Povarov反应）和氢转移过程。在合适的条件下，在酸催化剂的存在下，富电子的烯烃与过量的亚胺的反应在一次操作中得到取代的喹啉。在级联过程中，催化剂（例如Tf2NH，TfOH和路易斯酸）催化两个机理不同的反应（自动串联催化）。我们还描述了制备的喹啉的合成效用。
• Cascade and one-pot processes providing substituted quinolines from aldimines and allylsilanes: auto-tandem catalysis of triflic imide
  作者：Naoya Shindoh、Hidetoshi Tokuyama、Kiyosei Takasu

  DOI：10.1016/j.tetlet.2007.05.032

  日期：2007.7

  We have demonstrated cascade and one-pot reactions, which constitute inverse electron demand hetero-Diels-Alder reaction and oxidative aromatization, to provide substituted quinolines to form aryl aldimines and allylsilanes. The cascade process involves an auto-tandem catalysis; Tf2NH activates these mechanistically distinct reactions. We have found that a multicomponent process starting from aniline, aldehyde, and allylsilane is also available. (c) 2007 Elsevier Ltd. All rights reserved.