N,N′-[adamantane-1,3-diylbis(ethane-2,1-diyl)]-dipyridin-3-amine | 1421770-43-5

• 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,N′-[adamantane-1,3-diylbis(ethane-2,1-diyl)]-dipyridin-3-amine
• 英文别名: N,N'-[adamantane-1,3-diylbis(ethane-2,1-diyl)]-dipyridin-3-amine；N-[2-[3-[2-(pyridin-3-ylamino)ethyl]-1-adamantyl]ethyl]pyridin-3-amine
• CAS: 1421770-43-5
• 化学式: C₂₄H₃₂N₄
• 分子量: 376.545
• InChiKey: FJNZYFNUXCDRAZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 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：

  3-碘吡啶 、 1,3-金刚烷二乙胺 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， 生成 N,N′-[adamantane-1,3-diylbis(ethane-2,1-diyl)]-dipyridin-3-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

• Arylation of adamantanamines: VI. Palladium-catalyzed arylation of amines and diamines of the adamantane series with 3-bromopyridine
  作者：A. D. Averin、T. Yu. Baranova、A. S. Abel、V. V. Kovalev、A. K. Buryak、G. M. Butov、E. N. Savelyev、B. S. Orlinson、I. A. Novakov、I. P. Beletskaya

  DOI：10.1134/s1070428013010016

  日期：2013.1

  Palladium-catalyzed amination of 3-bromopyridine with amines of the adamantane series in the presence of Pd(dba)(2)/L [L = 2,2'-bis(diphenylphosphino)-1,1'-binaphthyl or 2-dimethylamino-2'-dicyclohexylphosphinobiphenyl] gave the desired N-(pyridin-3-yl)-substituted amines in 74-97% yields. Diamines of the adamantane series reacted with 2 equiv of 3-bromopyridine in a complicated fashion to produce mono- and triaryl-substituted derivatives as by-products, while the yields of N,N'-diarylation products were 18-56%. DOI: 10.1134/S1070428013010016