N-(adamantan-2-yl)pyridin-2-amine

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: N-(adamantan-2-yl)pyridin-2-amine
• 英文别名: N-((1r,3r,5r,7r)-adamantan-2-yl)pyridin-2-amine；Adamant-2-yl-α-pyridylamin；N-(2-adamantyl)pyridin-2-amine
• 化学式: C₁₅H₂₀N₂
• 分子量: 228.337
• InChiKey: GJPOAVIWMZYYSU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  24.9
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  2-甲氧基吡啶 、 2-氨基金刚烷 在 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 0.67h， 以56%的产率得到N-(adamantan-2-yl)pyridin-2-amine
  参考文献：
  名称：

  用脂肪胺快速胺化甲氧基吡啶

  摘要：

  开发了n- BuLi引发的甲氧基吡啶衍生物与脂肪族胺的实际胺化方案。对于伯胺，该反应可以在30分钟内完成；对于仲胺，该反应可以在10分钟内完成。出色的反应性和底物范围进一步突出了胺化反应。

  DOI：

  10.1021/acs.oprd.9b00235

文献信息

• Catalyst-free amination of 2-fluoropyridine and 2-fluoro-5-halopyridines with adamantane amines
  作者：A. S. Abel、O. K. Grigorova、A. D. Averin、O. A. Maloshitskaya、O. A. Popov、G. M. Butov、E. N. Savelyev、B. S. Orlinson、I. A. Novakov、I. P. Beletskaya

  DOI：10.1007/s11172-015-0919-1

  日期：2015.3

  Catalyst-free reactions of 2-fluoropyridine with amines and diamines bearing the adamantyl moiety at either the N atom or in the side chain were studied. Amines, which do not contain secondary alkyl substituents at the amino group, react with an excess of 2-fluoropyridine to give N-(pyridin-2-yl) derivatives in the yields from moderate to good. 2-Fluoro-5-halopyridines were found to be more reactive

  研究了 2-氟吡啶与在 N 原子或侧链中带有金刚烷基部分的胺和二胺的无催化剂反应。在氨基上不含仲烷基取代基的胺与过量的 2-氟吡啶反应生成 N-(吡啶-2-基)衍生物，产率从中等到高。发现 2-氟-5-卤代吡啶比 2-氟吡啶更具反应性。
• Arylation of adamantanamines: VII. Copper(I)-catalyzed N-heteroarylation of adamantane-containing amines with halopyridines
  作者：A. S. Abel、A. D. Averin、M. V. Anokhin、O. A. Maloshitskaya、G. M. Butov、E. N. Savelyev、B. S. Orlinson、I. A. Novakov、I. P. Beletskaya

  DOI：10.1134/s1070428015030021

  日期：2015.3

  Copper(I)-catalyzed N-heteroarylation of a wide series of adamantane-containing amines with 2-bromo- and 2- and 3-iodopyridines was studied. The corresponding N-pyridyl derivatives were formed in all cases, but iodopyridines were considerably more reactive. The best results were obtained with the catalytic system CuI-2-(2-methyl-1-oxopropyl)cyclohexanone-DMF which ensured up to 90% yield of the target products. The yield of N-pyridyl derivatives also depended on the steric environment of the amino group in the initial adamantane-containing amine. The yield of the heteroarylation products can be considerably increased using excess iodopyridine. The reaction of 2-(adamantan-1-yl)ethanamine with 2,6-dibromopyridine successfully afforded the corresponding diamine, and N,N'-dipyridyl derivatives were obtained in high yields from 2,2'-(adamantane-1,3-diyl)diethanamine.