1-(1-adamantyl)pyrrole | 5511-17-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: 1-(1-adamantyl)pyrrole
• 英文别名: 1-(adamantyl)-1H-pyrrole；N-(1-adamantyl)-1H-pyrrole；adamantanyl-1H-pyrrole；N-(1-Adamantyl)-pyrrol；1-(adamantan-1-yl)-1H-pyrrole；1-adamantan-1-yl-pyrrole；1-(1-Adamantyl)-1H-pyrrole
• CAS: 5511-17-1
• 化学式: C₁₄H₁₉N
• 分子量: 201.312
• InChiKey: FPDMMEYWYCEYGO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.714
• 拓扑面积：
  4.9
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  1-(1-adamantyl)pyrrole 、 三氟乙酸酐 以 苯 为溶剂， 反应 4.0h， 以5.8 g的产率得到1-(1-adamantyl)-3-trifluoroacetylpyrrole
  参考文献：
  名称：

  Chadwick, Derek J.; Meakins, G. Denis; Rhodes, Caroline A., Journal of Chemical Research, Miniprint, 1980, # 2, p. 878 - 886

  摘要：

  DOI：
• 作为产物：
  描述：

  1-溴金刚烷 在 sodium azide 、 hydrazine hydrate 、 caesium carbonate 作用下， 以 甲醇 、 二甲基亚砜 、 甲苯 为溶剂， 反应 36.5h， 生成 1-(1-adamantyl)pyrrole
  参考文献：
  名称：

  单原子钴催化叠氮化物转移氢化及吡咯一锅法合成

  摘要：

  在这项工作中，报道了在温和条件下（30°C，30 分钟）使用 NH 2 NH 2  ⋅ H 2 O 作为氢源，单原子钴催化叠氮化物的转移氢化（TH）。采用该方案，多种叠氮化物被转化为其相应的胺。该方法被扩展到以一锅法从叠氮化物合成几种重要的N-取代吡咯。对照实验表明，吸电子取代基有利于转移氢化，给电子取代基有利于一锅吡咯合成。可回收性测试表明，催化剂可回收最多 7次，催化活性没有明显损失。

  DOI：

  10.1002/adsc.202300556

文献信息

• An Expeditious Synthesis of N-substituted Pyrroles via Microwave-Induced Iodine-Catalyzed Reactions under Solventless Conditions
  作者：Debasish Bandyopadhyay、Sanghamitra Mukherjee、Bimal K. Banik

  DOI：10.3390/molecules15042520

  日期：——

  An expeditious synthesis of N-substituted pyrroles has been developed by reacting 2,5-dimethoxy tetrahydrofuran and several amines using a microwave-induced molecular iodine-catalyzed reaction under solventless conditions.

  在无溶剂条件下，利用微波诱导的碘分子催化反应，使 2,5 二甲基四氢呋喃和几种胺发生反应，从而开发出一种快速合成 N-取代吡咯的方法。
• Frustrated Lewis pair-catalyzed double hydroarylation of alkynes with <i>N</i>-substituted pyrroles
  作者：Jing Guo、Odelia Cheong、Karlee L. Bamford、Jiliang Zhou、Douglas W. Stephan

  DOI：10.1039/c9cc08654d

  日期：——

  of alkynes with N-substituted pyrroles is shown to be most efficiently mediated by B(C6F5)3 to yield 12 variants of dipyrrole-alkanes, a mono-hydroarylation product and a tetrahydroarylation product of a bis-alkyne. These products were generally obtained in good to excellent yields (up to 95%). Control experiments suggest a mechanism involving FLP addition of the borane and pyrrole to alkyne.

  炔烃与N-取代的吡咯的无金属加氢芳基化反应最有效地由B（C6F5）3介导，可生成12个变体的双吡咯烷烃，双炔烃的单加氢芳基化产物和四氢化芳基化产物。这些产品通常以高至极好的收率（高达95％）获得。对照实验提出了一种机制，该机制涉及通过FLP将硼烷和吡咯添加到炔烃中。
• Iron-Catalyzed Sustainable Synthesis of Pyrrole
  作者：Balakumar Emayavaramban、Malay Sen、Basker Sundararaju

  DOI：10.1021/acs.orglett.6b02819

  日期：2017.1.6

  sustainable, highly regiospecific substituted pyrroles were synthesized using a well-defined, air stable, molecular iron(0) complex. The developed methodology is broadly applicable and tolerates a variety of functional groups. C-2, C-3, and C-2 & C-4 substituted pyrroles were synthesized in good yield. Symmetrical bis-pyrroles were accessible for the first time using an iron catalyst. On the basis of the experimental

  使用定义明确，空气稳定的分子铁（0）配合物合成了高效，可持续的，高度区域特异性的取代吡咯。所开发的方法学广泛适用，并且可以容忍各种功能组。以高收率合成了C-2，C-3以及C-2和C-4取代的吡咯。对称的双吡咯是首次使用铁催化剂获得。基于实验观察，我们建议反应通过氢自动转移过程进行，然后进行第二次氧化/分子内脱水缩合以提供吡咯。
• Facile synthesis of N-substituted pyrroles via microwave-induced bismuth nitrate-catalyzed reaction
  作者：Sonya Rivera、Debasish Bandyopadhyay、Bimal K. Banik

  DOI：10.1016/j.tetlet.2009.06.002

  日期：2009.9

  Simple synthesis of N-substituted pyrroles using microwave-induced bismuth nitrate-catalyzed reaction has been accomplished with an excellent yield. A plausible mechanism has been advanced. This reaction also provides a simple method to prepare diverse varieties of N-substituted pyrrole derivatives with less nucleophilic polyaromatic amines. (C) 2009 Published by Elsevier Ltd.
• Ultrasound-assisted bismuth nitrate-induced green synthesis of novel pyrrole derivatives and their biological evaluation as anticancer agents
  作者：Debasish Bandyopadhyay、Sanghamitra Mukherjee、Jose C. Granados、John D. Short、Bimal K. Banik

  DOI：10.1016/j.ejmech.2012.01.055

  日期：2012.4

  A series of novel N-substituted pyrrole derivatives have been designed and synthesized following ultrasound-assisted and bismuth nitrate-catalyzed eco-friendly route. This reaction has also provided a general method to prepare diverse varieties of N-substituted pyrroles with less nucleophilic polyaromatic amines. Based on H-1 NMR spectroscopy, a plausible mechanistic pathway has been advanced. Cytotoxicity of some selected N-substituted pyrrole derivatives has been evaluated in vitro in a panel of mammalian cancer cell lines which includes liver cancer cell lines (HepG2 and Hepa1-6), colon cancer cell lines (HT-29 and Caco-2), a cervical cancer cell line (HeLa) and NIH3T3 cells. Two compounds, 5-(1H-pyrrol-1-yl)-1,10-phenanthroline (9) and 1-(phenanthren-2-yl)-1H-pyrrole (10) have shown good cytotoxicity against some cancer cell lines. Furthermore, these compounds have exhibited cytotoxic specificity against liver cancer cell lines in vitro when compared with normal cultured primary hepatocytes. (C) 2012 Published by Elsevier Masson SAS.