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.
• Rapid Amination of Methoxy Pyridines with Aliphatic Amines
  作者：Xia Wang、Cheng-Yu Long、Min-Hui Su、Yi-Xin Qu、Shen-Huan Li、Xiao-Jing Zhang、Si-Jie Huang、Xue-Qiang Wang

  DOI：10.1021/acs.oprd.9b00235

  日期：2019.8.16

  A n-BuLi triggered practical amination protocol of methoxy pyridine derivatives with aliphatic amines was developed. The reaction could finish in 30 min for primary amines and 10 min for secondary amines. The amination is further highlighted by its excellent reactivity and substrate scope.

  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。