N-(2-金刚烷基)吡啶-3-胺 | 126947-67-9

• 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
• 中文名称: N-(2-金刚烷基)吡啶-3-胺
• 英文名称: N-(adamantan-2-yl)pyridin-3-amine
• 英文别名: 3-(adamant-2-ylamino)pyridine；3-(Adamant-3-ylamino)pyridine；N-(2-adamantyl)pyridin-3-amine
• CAS: 126947-67-9
• 化学式: C₁₅H₂₀N₂
• 分子量: 228.337
• InChiKey: NJIYTWCEQIQWDC-UHFFFAOYSA-N

物化性质

• 熔点：
  104-105 °C(Solv: water (7732-18-5); ethanol (64-17-5))
• 沸点：
  384.1±15.0 °C(Predicted)
• 密度：
  1.155±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.666
• 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：

  3-碘吡啶 、 2-氨基金刚烷 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-(2-金刚烷基)吡啶-3-胺
  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

• Adamantylpyridines and their biological activities
  作者：N. V. Klimova、N. M. Zaitseva、N. I. Avdyunina、B. M. Pyatin、I. C. Morozov、N. P. Bykov、V. I. Kuz'min

  DOI：10.1007/bf00769382

  日期：1990.1

  Adamantane derivatives are also known to exhibit positive inotropic action resulting from blockage of the calcium channels [17]. The wide spectrum of biological activities exhibited by these classes of compounds provides a perspective for investigations in the synthesis and study of the pharmacological activities in the adamantylpyridine series. With the goal of studying the effects of introducing the pyridine

  在属于取代吡啶类的化合物中发现了广泛的药理活性，包括抗心绞痛和高血压 [13, 14]、血管扩张剂 [15, 16]、抗氧化和精神活性 [3-6, 12]。金刚烷衍生物，例如精神药物和抗抑郁化合物 gludantan [6] 和阿达帕明 [2]，以及金刚烷基吩噻嗪和苯胺系列的免疫药物化合物也具有多种药理特性。还已知金刚烷衍生物由于钙通道的阻塞而表现出正性肌力作用 [17]。这些类别的化合物表现出的广泛生物活性为研究合成和研究金刚烷基吡啶系列的药理活性提供了前景。为了研究引入吡啶基团对金刚烷衍生物药理谱的影响，进行了几种金刚烷基吡啶的定向合成。使用 Leuckart 反应，金刚烷-2-酮和氨基吡啶缩合得到 3-(金刚烷-2-基氨基)吡啶 (I) 和 4(金刚烷-2-基氨基)吡啶 (II) [8]。为了对金刚烷的伯、仲和叔醇衍生物的酯化作用进行比较药理学研究，合成了烟酸和 5-溴烟酸 (III-VI)
• 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
• KLIMOVA, N. V.;ZAJTSEVA, N. M.;AVDYUNINA, N. I.;PYATIN, B. M.;MOROZOV, I.+, XIM.-FARMATS. ZH., 24,(1990) N, S. 26-29
  作者：KLIMOVA, N. V.、ZAJTSEVA, N. M.、AVDYUNINA, N. I.、PYATIN, B. M.、MOROZOV, I.+

  DOI：——

  日期：——
• 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.