2-(imidazol-1-yl)-3-methylpyridine | 1343738-06-6

• 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: 2-(imidazol-1-yl)-3-methylpyridine
• 英文别名: 1-(3-methylpyridin-2-yl)imidazole；2-(1H-imidazol-1-yl)-3-methylpyridine；2-Imidazol-1-yl-3-methylpyridine
• CAS: 1343738-06-6
• 化学式: C₉H₉N₃
• 分子量: 159.191
• InChiKey: RBQFDAUQPBUXTR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  30.7
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-(imidazol-1-yl)-3-methylpyridine 在 ammonium hexafluorophosphate 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 48.0h， 生成
  参考文献：
  名称：

  On the Concept of Hemilability: Insights into a Donor-Functionalized Iridium(I) NHC Motif and Its Impact on Reactivity

  摘要：

  Novel iridium(I) complexes bearing N-donor-functionalized N-heterocyclic carbene ligands were synthesized. Although hemilabile coordination of the attached donor is considered beneficial in catalysis, no detailed study of this phenomenon in these systems is available to date. The present report provides insight into the hemilabile bonding properties of a N,N'-bis(pyridin-2-yl)-imidazolylidene (NCN) ligand motif on iridium(I). In most cases, the presented compounds exhibit rare fluxional hemilabile coordination of the N donor, and remarkable performance in catalytic transfer hydrogenation is observed. Further, extensive reactivity studies often led to unexpected products.

  DOI：

  10.1021/ic5016324
• 作为产物：
  描述：

  咪唑 、 2-溴-3-甲基吡啶 在 potassium carbonate 作用下， 以 neat (no solvent) 为溶剂， 反应 18.0h， 以89%的产率得到2-(imidazol-1-yl)-3-methylpyridine
  参考文献：
  名称：

  Facile and scalable preparation of 2-imidazolylpyridines

  摘要：

  A novel method for the synthesis of 2-imidazolylpyridines is presented. The reaction of 2-halopyridines, potassium carbonate, and imidazole at high temperatures under inert gas atmosphere leads exclusively to the formation of 2-imidazolylpyridines in high yields. The synthesis is scalable, comparatively inexpensive, and the products are easily isolable. (c) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2013.04.060

文献信息

• Leveraging Metallotropism-Enabled Substrate Activation in Cobalt-Catalyzed Annulation Chemistry: Protic NHC Template Is the Key
  作者：Champak Dutta、Samim Sohel Rana、Joyanta Choudhury

  DOI：10.1021/acscatal.9b04125

  日期：2019.12.6

  functionalization of azoles with internal alkynes, providing a variety of π-extended polycyclic heteroarene compounds. Mechanistic investigations via isolation and structure elucidation of the key pNHC-Co intermediates followed by control stoichiometric and catalytic reactions highlighted the crucial electronic control on the azole C–H activation, alkyne insertion, and regiodivergent annulation steps involved

  这项研究介绍了质子NHC（p NHC）与Cp * Co（III）物种的配合物，通过金属弹塑性触发的普遍存在的唑底物的激活而获得。这些“ Co III - p NHC”模板在用内部炔烃催化的环氧基官能化唑中得到了进一步探索，从而提供了多种π扩展的多环杂芳烃化合物。通过关键P的隔离和结构解析进行的机械研究NHC-Co中间体随后进行化学计量和催化反应控制，突显了此催化方案中涉及的唑C–H活化，炔烃插入和区域发散环化步骤的关键电子控制。这些结果表明，基于钴的金属成缆作用可作为实现地球富裕的第一行过渡金属催化的C–H功能化的潜在有用平台，并与基于贵金属的主导策略相辅相成。
• Facile and scalable preparation of 2-imidazolylpyridines
  作者：Andreas Raba、Markus R. Anneser、Dominik Jantke、Mirza Cokoja、Wolfgang A. Herrmann、Fritz E. Kühn

  DOI：10.1016/j.tetlet.2013.04.060

  日期：2013.6

  A novel method for the synthesis of 2-imidazolylpyridines is presented. The reaction of 2-halopyridines, potassium carbonate, and imidazole at high temperatures under inert gas atmosphere leads exclusively to the formation of 2-imidazolylpyridines in high yields. The synthesis is scalable, comparatively inexpensive, and the products are easily isolable. (c) 2013 Elsevier Ltd. All rights reserved.
• On the Concept of Hemilability: Insights into a Donor-Functionalized Iridium(I) NHC Motif and Its Impact on Reactivity
  作者：Korbinian Riener、Mario J. Bitzer、Alexander Pöthig、Andreas Raba、Mirza Cokoja、Wolfgang A. Herrmann、Fritz E. Kühn

  DOI：10.1021/ic5016324

  日期：2014.12.15

  Novel iridium(I) complexes bearing N-donor-functionalized N-heterocyclic carbene ligands were synthesized. Although hemilabile coordination of the attached donor is considered beneficial in catalysis, no detailed study of this phenomenon in these systems is available to date. The present report provides insight into the hemilabile bonding properties of a N,N'-bis(pyridin-2-yl)-imidazolylidene (NCN) ligand motif on iridium(I). In most cases, the presented compounds exhibit rare fluxional hemilabile coordination of the N donor, and remarkable performance in catalytic transfer hydrogenation is observed. Further, extensive reactivity studies often led to unexpected products.