1,3-bis[2-(2-pyridylamino)ethyl]adamantane

• 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: 1,3-bis[2-(2-pyridylamino)ethyl]adamantane
• 英文别名: N,N'-bis(pyridin-2-yl)-2,2'-(adamantane-1,3-diyl)diethanamine；N-[2-[3-[2-(pyridin-2-ylamino)ethyl]-1-adamantyl]ethyl]pyridin-2-amine
• 化学式: C₂₄H₃₂N₄
• 分子量: 376.545
• InChiKey: KSUOJJXTFSLYBD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.1
• 重原子数：
  28
• 可旋转键数：
  8
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  49.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  2-氟吡啶 、 1,3-金刚烷二乙胺 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 以70%的产率得到1,3-bis[2-(2-pyridylamino)ethyl]adamantane
  参考文献：
  名称：

  使用金刚烷胺对 2-氟吡啶和 2-氟-5-卤代吡啶进行无催化剂胺化

  摘要：

  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。

  DOI：

  10.1007/s11172-015-0919-1

文献信息

• Synthesis of a New Family of Adamantylpyridin-2-amines by Palladium-Catalyzed­ Amination
  作者：Alexei Averin、Irina Beletskaya、Elena Ranyuk、Svetlana Golub、Alexei Buryak、Evgenii Savelyev、Boris Orlinson、Ivan Novakov

  DOI：10.1055/s-2007-983760

  日期：——

  Palladium-catalyzed arylation of various adamantane-containing amines with 2-bromopyridine has been studied, and the influence of the phosphane ligand, concentration, and molar ratio of the reagents on the composition of the reaction mixture and on the yield of the target adamantylpyridin-2-amines has been analyzed. The dependence of the formation of N,N-diarylated products on the nature of the starting adamantylamines is shown.

  已研究了钯催化的不同含有金刚烷的胺与2-溴吡啶的芳香化反应，分析了磷配体、浓度和试剂的摩尔比对反应混合物组成以及目标金刚烷吡啶-2-胺产率的影响。结果表明，N,N-二芳基化产物的形成依赖于起始金刚烷胺的性质。
• 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.