N-[(1-adamantyl)(phenyl)methyl]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-[(1-adamantyl)(phenyl)methyl]pyridin-2-amine
• 英文别名: N-[1-adamantyl(phenyl)methyl]pyridin-2-amine
• 化学式: C₂₂H₂₆N₂
• 分子量: 318.462
• InChiKey: PQAMNKFSPXPCCB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.5
• 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：

  1-(α-aminobenzyl)adamantane 、 2-碘吡啶 在 copper(l) iodide 、 2-(2-甲基-1-氧代丙烷)环己酮 、 caesium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 生成 N-[(1-adamantyl)(phenyl)methyl]pyridin-2-amine
  参考文献：
  名称：

  Arylation of adamantanamines: VII. Copper(I)-catalyzed N-heteroarylation of adamantane-containing amines with halopyridines

  摘要：

  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.

  DOI：

  10.1134/s1070428015030021

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。
• The Palladium-Catalyzed Heteroarylation of Adamantylalkyl Amines with Dihalogenopyridines: Scope and Limitations
  作者：Irina Beletskaya、Anton Abel、Alexei Averin、Alexei Buryak、Evgenii Savelyev、Boris Orlinson、Ivan Novakov

  DOI：10.1055/s-0036-1590860

  日期：2017.11

  coupling on the nature of the halogen atoms (bromine, chlorine), their position in the pyridine ring, and on the structure of adamantylalkyl amines was investigated. The application of dichloropyridines or bromochloropyridines was shown to be advantageous over the use dibromopyridines in many cases. Selective substitution of bromine atom in positions 3 and 5 in the presence of chlorine atom in position

  摘要 使用2,3-，2,5-，2,6-和3,5-二卤代吡啶进行钯催化的金刚烷基烷基胺的杂芳基化，其特征在于氨基上的空间位阻不同。研究了偶联结果对卤素原子（溴，氯）的性质，它们在吡啶环中的位置以及金刚烷基烷基胺的结构的依赖性。在许多情况下，使用二氯吡啶或溴氯吡啶显示出优于使用二溴吡啶的优势。在吡啶环的2位上存在氯原子的情况下，观察到3和5位上的溴原子的选择性取代。N，N的可能性显示了含金刚烷胺与2，5-二卤代吡啶的二异芳基化，并证明了2，6-和3，5-二卤代吡啶的苯胺化。 使用2,3-，2,5-，2,6-和3,5-二卤代吡啶进行钯催化的金刚烷基烷基胺的杂芳基化，其特征在于氨基上的空间位阻不同。研究了偶联结果对卤素原子（溴，氯）的性质，它们在吡啶环中的位置以及金刚烷基烷基胺的结构的依赖性。在许多情况下，使用二氯吡啶或溴氯吡啶显示出优于使用二溴吡啶的优势。在吡啶环的2位上存在氯原子的情况下，观察
• 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.