N-(1-(adamantan-1-yl)propan-2-yl)aniline | 1283234-27-4

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: N-(1-(adamantan-1-yl)propan-2-yl)aniline
• CAS: 1283234-27-4
• 化学式: C₁₉H₂₇N
• 分子量: 269.43
• InChiKey: PRLBVHBXGXGTDP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.09
• 重原子数：
  20.0
• 可旋转键数：
  4.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.68
• 拓扑面积：
  12.03
• 氢给体数：
  1.0
• 氢受体数：
  1.0

反应信息

• 作为产物：
  描述：

  碘苯 、 1-(1-adamantyl)propan-2-amine 在 2-(2-甲基-1-氧代丙烷)环己酮 、 caesium carbonate 作用下， 以 二甲基亚砜 为溶剂， 反应 24.0h， 生成 N-(1-(adamantan-1-yl)propan-2-yl)aniline
  参考文献：
  名称：

  均相和多相铜催化胺芳基化的比较

  摘要：

  在 DMSO 中比较模型伯胺与（杂）-芳基碘化物的均相和非均相铜催化芳基化反应表明，在 2-异丁酰基-环己酮或L-脯氨酸。

  DOI：

  10.1016/j.mencom.2022.01.029

文献信息

• Arylation of adamantanamines: II. Palladium-catalyzed amination of dihalobenzenes with adamantylalkanamines
  作者：A. D. Averin、M. A. Ulanovskaya、A. K. Buryak、E. N. Savel’ev、B. S. Orlinson、I. A. Novakov、I. P. Beletskaya

  DOI：10.1134/s1070428010120055

  日期：2010.12

  Palladium-catalyzed arylation of various (1-adamantyl)alkanamines with isomeric (ortho, meta, and para) bromochloro- and dibromobenzenes was studied. Optimal catalytic systems were found for the synthesis of mono- and diamination products, and the dependences of their yields on the nature of the initial amine and dihalobenzene and on the amount of base were examined. Side amination products were isolated, and paths of their formation were analyzed.
• Comparison of the Catalytic Activities of Copper(I) Iodide and Copper Nanoparticles in the N-Arylation of Adamantane-Containing Amines
  作者：A. V. Murashkina、A. D. Averin、S. P. Panchenko、A. S. Abel、O. A. Maloshitskaya、E. N. Savelyev、B. S. Orlinson、I. A. Novakov、C. R. D. Correia、I. P. Beletskaya

  DOI：10.1134/s107042802201002x

  日期：2022.1
• Arylation of adamantanamines: VIII. Optimization of the catalytic system for copper-catalyzed arylation of adamantane-containing amines
  作者：S. P. Panchenko、A. S. Abel、A. D. Averin、O. A. Maloshitskaya、E. N. Savelyev、B. S. Orlinson、I. A. Novakov、I. P. Beletskaya

  DOI：10.1134/s1070428017100025

  日期：2017.10

  Arylation of adamantane-containing amines with iodobenzene in the presence of copper(I) and copper(II) compounds and various N,N-, N,O-, and O,O-bidentate ligands was studied. The best results were obtained using the catalytic system CuI-rac-BINOL [1,1'-bi(naphthalen-2-ol)] (10/20 mol %). Reactions with iodobenzene derivatives containing electron-donor and electron-withdrawing substituents in the para position to the iodine atom were carried out under the optimal conditions.