N-(2-allylbenzyl)aniline | 196085-29-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: N-(2-allylbenzyl)aniline
• 英文别名: N-[(2-prop-2-enylphenyl)methyl]aniline
• CAS: 196085-29-7
• 化学式: C₁₆H₁₇N
• 分子量: 223.318
• InChiKey: XGGPZZPWRPHDTF-UHFFFAOYSA-N

物化性质

• 沸点：
  347.6±11.0 °C(Predicted)
• 密度：
  1.043±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.03
• 重原子数：
  17.0
• 可旋转键数：
  5.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  12.03
• 氢给体数：
  1.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  N-(2-allylbenzyl)aniline 在 正丁基锂 、 zirconocene methyl chloride 作用下， 以82%的产率得到((1R,2R)-2-Methyl-indan-1-yl)-phenyl-amine
  参考文献：
  名称：

  Zirconium-Mediated Intramolecular Coupling Reactions of Unsaturated Anilines. Diastereoselective Synthesis of Azetidines

  摘要：

  Imine complexes of zirconocene, generated by a beta-hydrogen abstraction process, which possess a carbon-carbon multiple bond, undergo inter-or intramolecular carbometalation to afford 1,4-cyclohexanediamine or cycloalkylaniline derivatives depending on the relative position of the unsaturated moiety with respect to the imine complex. A new diastereoselective synthesis of azetidines has been developed by treatment of azazirconacyclopentanes with iodine.

  DOI：

  10.1021/jo9705780
• 作为产物：
  描述：

  苯甲基苯胺 、 3-氯丙烯 在 正丁基锂 、 四甲基乙二胺 作用下， 生成 N-(2-allylbenzyl)aniline
  参考文献：
  名称：

  Zirconium-Mediated Intramolecular Coupling Reactions of Unsaturated Anilines. Diastereoselective Synthesis of Azetidines

  摘要：

  Imine complexes of zirconocene, generated by a beta-hydrogen abstraction process, which possess a carbon-carbon multiple bond, undergo inter-or intramolecular carbometalation to afford 1,4-cyclohexanediamine or cycloalkylaniline derivatives depending on the relative position of the unsaturated moiety with respect to the imine complex. A new diastereoselective synthesis of azetidines has been developed by treatment of azazirconacyclopentanes with iodine.

  DOI：

  10.1021/jo9705780

文献信息

• Asymmetric Synthesis of Fused Tetrahydroquinolines via Intra­molecular Aza-Diels–Alder Reaction of ortho-Quinone Methide Imines
  作者：Christoph Schneider、Fabian Hofmann、Cornelius Gärtner、Martin Kretzschmar

  DOI：10.1055/a-1517-7515

  日期：2022.2

  bicyclic core structures with up to three stereocenters within a single step. Herein, this concept is combined with the chemistry of chiral Brønsted acid bound ortho-quinone methide imines to generate a range of interesting fused tetrahydroquinolines in a diastereo- and enantioselective­ manner.

  Aza-Diels-Alder 反应是构建 N-杂环的直接过程，具有固有的原子经济性和立体定向性。分子内策略允许在单个步骤中形成具有多达三个立体中心的双环核心结构。在此，该概念与手性布朗斯台德酸键合邻醌甲基亚胺的化学相结合，以非对映选择性和对映选择性方式生成一系列有趣的稠合四氢喹啉。
• Decarboxylative Aminomethylation of Aryl- and Vinylsulfonates through Combined Nickel- and Photoredox-Catalyzed Cross-Coupling
  作者：Lulu Fan、Jiaqi Jia、Hong Hou、Quentin Lefebvre、Magnus Rueping

  DOI：10.1002/chem.201604452

  日期：2016.11.7

  mild approach for the decarboxylative aminomethylation of aryl sulfonates by the combination of photoredox and nickel catalysis through C−O bond cleavage is described for the first time. A wide range of aryl triflates as well as aryl mesylates, tosylates and alkenyl triflates afford the corresponding products in good to excellent yields.

  首次描述了一种温和的方法，该方法通过光氧还原和镍催化（通过C-O键断裂）的结合，对芳基磺酸盐进行脱羧氨基甲基化。各种各样的芳基三氟甲磺酸酯以及甲磺酸甲磺酸酯，甲苯磺酸酯和烯基三氟甲磺酸酯以良好或优异的收率提供了相应的产物。