(3s,5s,7s)-N-(3-nitrophenyl)adamantan-1-amine | 208262-17-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (3s,5s,7s)-N-(3-nitrophenyl)adamantan-1-amine
• 英文别名: N-(1-adamantyl)-3-nitroaniline；N-(3-nitrophenyl)adamantan-1-amine
• CAS: 208262-17-3
• 化学式: C₁₆H₂₀N₂O₂
• 分子量: 272.347
• InChiKey: AVWCPSYKIJXPED-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  57.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  金刚烷 、 间硝基苯胺 在 aluminum tri-bromide 、 四溴化碳 作用下， 以 neat (no solvent) 为溶剂， 反应 0.08h， 以90%的产率得到(3s,5s,7s)-N-(3-nitrophenyl)adamantan-1-amine
  参考文献：
  名称：

  Solvent-free and direct C(sp3)–H amination of adamantanes by grinding

  摘要：

  A facile, direct and environmentally benign conversion of C(sp(3))-H bonds to C(sp(3))-N bonds using substoichiometric amount of aprotic superelectrophiles polyhalomethane-AIX(3) has been achieved by grinding under solvent-free conditions at room temperature in air. It is a general and simple method for the direct amination of adamantanes, and a series of aminoadamantanes of azoles, arylamines or heteroarylamines were obtained in good to excellent yields. The advantages of this amination are atom economy, solvent-free, chemoselectivity, short reaction time and high yields. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2014.01.014

文献信息

• Synthesis of N-adamantylated mononitro derivatives of aromatic amines in trifluoro- and dichloroacetic acids
  作者：V. G. Tsypin、V. A. Polukeev

  DOI：10.1134/s1070363210030321

  日期：2010.3

  Here we report on the study of the alkylation of 2nitro-, 3-nitroand 4-nitroanilines III–V with 1-(trifluoroacetoxy)adamantane II. The acidity function рKА of trifluoroacetic acid, catalyst and medium, is 0.52 [6]. Unlike 1-adamantanol I, the conversion of the start-ing ester II in trifluoroacetic acid does not result in water formation, and as a consequence leads to no changes in the medium acidity

  在这里，我们报告了用 1-（三氟乙酰氧基）金刚烷 II 烷基化 2-硝基、3-硝基和 4-硝基苯胺 III-V 的研究。三氟乙酸、催化剂和介质的酸度函数 рK- 为 0.52 [6]。与 1-金刚烷醇 I 不同，起始酯 II 在三氟乙酸中的转化不会导致水形成，因此在反应过程中不会导致介质酸度发生变化。我们发现硝基苯胺 III-V 与三氟乙酸中的 1-（三氟乙酰氧基）金刚烷 II 反应平稳，主要形成相应的 N-烷基化产物 VI-VIII。与碱性最低的 2-硝基苯胺 III (рKВН –0.31, –0.26 [7, 8]) 的反应甚至在 18-20oС 时也能进行，并在 5 天内生成 N-(1-金刚烷基)-2-硝基苯胺 VI 和4(1-金刚烷基)-2-硝基苯胺 IX，比例为 94.3:5。分别为 7 %（质量）（通过 Н NMR）。从 80% 的 2-丙醇水溶液中重结晶，以 58.7-61
• Adamantylation of nitro-substituted aromatic amines in protic acids
  作者：S. B. Volkova、O. V. Platonova、V. G. Tsypin、V. A. Polukeev

  DOI：10.1134/s1070363208090132

  日期：2008.9

  Adamantylation of mono-and dinitro-substituted aromatic amines in sulfuric and phosphoric acids and in a mixture of phosphoric and acetic acids gives mainly the corresponding N-adamantyl derivatives. The results of kinetic measurements showed reversible character of the process.
• Solvent-free and direct C(sp3)–H amination of adamantanes by grinding
  作者：Zhen Wei、Jiarong Li、Ning Wang、Qi Zhang、Daxin Shi、Kening Sun

  DOI：10.1016/j.tet.2014.01.014

  日期：2014.2

  A facile, direct and environmentally benign conversion of C(sp(3))-H bonds to C(sp(3))-N bonds using substoichiometric amount of aprotic superelectrophiles polyhalomethane-AIX(3) has been achieved by grinding under solvent-free conditions at room temperature in air. It is a general and simple method for the direct amination of adamantanes, and a series of aminoadamantanes of azoles, arylamines or heteroarylamines were obtained in good to excellent yields. The advantages of this amination are atom economy, solvent-free, chemoselectivity, short reaction time and high yields. (C) 2014 Elsevier Ltd. All rights reserved.