1-amino-2-(2-adamantyl)butane | 1431612-18-8

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 1-amino-2-(2-adamantyl)butane
• 英文别名: 2-(adamant-2-yl)butan-1-amine；2-(adamant-2-yl)butane-1-amine；2-(tricycloc[3.3.1.1^3,7]dec-2-yl)butan-1-amine；2-(2-adamantyl)butan-1-amine
• CAS: 1431612-18-8
• 化学式: C₁₄H₂₅N
• 分子量: 207.359
• InChiKey: KPGJZTPTIRYMDG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  26
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  碘苯 、 1-amino-2-(2-adamantyl)butane 在 copper(l) iodide 、 caesium carbonate 、 S-1,1'-联-2-萘酚 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 以82%的产率得到N-[2-(adamantan-2-yl)butyl]aniline
  参考文献：
  名称：

  Arylation of adamantanamines: IX. Copper(I)-catalyzed arylation of adamantane-containing amines

  摘要：

  Copper(I)-catalyzed arylation of 14 adamantane-containing amines with iodobenzene, 1-fluoro-4-iodobenzene, 1-iodo-4-(trifluoromethyl) benzene, and 1-iodo-4-methoxybenzene has been studied under the conditions optimized previously. The yields of the N-arylation products have been shown to depend in a complicated manner on the amine structure, steric environment of the amino group, and substituent nature in iodobenzene.

  DOI：

  10.1134/s1070428017120028
• 作为产物：
  描述：

  2-(adamantane-2-ylidene)butanenitrile 在 lithium aluminium tetrahydride 作用下， 以 2-甲基四氢呋喃 为溶剂， 反应 10.0h， 以91%的产率得到1-amino-2-(2-adamantyl)butane
  参考文献：
  名称：

  在2-甲基四氢呋喃中用氢化锂铝还原不饱和含金刚烷腈

  摘要：

  研究了在2-甲基四氢呋喃中用氢化铝锂还原不饱和含金刚烷基的腈。发现在合成条件下，双键和腈基同时还原成功。在腈的金刚烷基部分的α位上存在大量取代基导致合成持续时间的显着增加。仅通过提高温度并使用两倍过量的氢化锂铝才能获得令人满意的目标化合物收率。

  DOI：

  10.1134/s1070363216060062

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。
• Condensation of adamantanone with methylene-active compounds
  作者：Yu. V. Popov、V. M. Mokhov、N. A. Tankabekyan

  DOI：10.1134/s1070427213030191

  日期：2013.3

  A convenient method was developed for the preparation of potentially bioactive substances with 2-adamantyl radical and of intermediates for their synthesis. Condensation of adamantanone with methylene-active compounds was performed, and the reaction features were determined.

  开发了一种方便的方法来制备具有2-金刚烷基自由基的潜在生物活性物质以及用于其合成的中间体。进行金刚烷酮与亚甲基活性化合物的缩合反应，并确定了反应特征。
• Synthesis of 2-adamantyl-containing amines as compounds with potential pharmacological activity
  作者：I. A. Novakov、B. S. Orlinson、E. N. Savel’ev、E. A. Alykova、A. M. Pichugin、M. A. Kovaleva、A. O. Sergeev、N. A. Demidovich、E. V. Kondrat’ev

  DOI：10.1007/s11172-022-3701-1

  日期：2022.12

  The regularities of the reduction of unsaturated nitriles containing the 2-adamantyl fragment with lithium aluminum hydride and nickel—aluminum alloy were studied. In both cases, the double bond and nitrile group were simultaneously reduced. The presence of bulky substituents in the substrate in the α-position to the adamantyl fragment and hydroxy groups significantly retards the process, and the 80–90% yield of the corresponding products is achieved only when the temperature is raised to 65 °C. In the case of using a nickel—aluminum alloy, its 4—6-fold excess is required. The calculation of the potential pharmacological activity of the synthesized compounds shows that they can have antiviral, analgesic, and antidiabetic activity.

  研究了用氢化锂铝和镍铝合金还原含有 2-金刚烷基片段的不饱和腈的规律性。在这两种情况下，双键和腈基同时被还原。底物中金刚烷基片段和羟基的 α 位上存在笨重的取代基会大大延缓这一过程，只有当温度升至 65 ℃ 时，相应产物的产率才能达到 80-90%。如果使用镍铝合金，则需要过量 4-6 倍。对合成化合物潜在药理活性的计算表明，它们具有抗病毒、镇痛和抗糖尿病活性。
• Comparison of the Catalytic Activities of Copper(I) Iodide and Copper Nanoparticles in the N-Arylation of Adamantane-Containing Amines
  作者：A. V. Murashkina、A. D. Averin、S. P. Panchenko、A. S. Abel、O. A. Maloshitskaya、E. N. Savelyev、B. S. Orlinson、I. A. Novakov、C. R. D. Correia、I. P. Beletskaya

  DOI：10.1134/s107042802201002x

  日期：2022.1
• CuI and Copper Nanoparticles in the Catalytic Amination of 2-Halopyridines
  作者：D. S. Kuliukhina、A. D. Averin、S. P. Panchenko、A. S. Abel、E. N. Savelyev、B. S. Orlinson、I. A. Novakov、C. R. D. Correia、I. P. Beletskaya

  DOI：10.1134/s1070428022020014

  日期：2022.2