3-(4-phenyl-1H-imidazol-1-yl)pyridine | 1351990-71-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 3-(4-phenyl-1H-imidazol-1-yl)pyridine
• 英文别名: 3-(4-Phenylimidazol-1-yl)pyridine；3-(4-phenylimidazol-1-yl)pyridine
• CAS: 1351990-71-0
• 化学式: C₁₄H₁₁N₃
• 分子量: 221.261
• InChiKey: FVJRQMBZSOJTNH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  30.7
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  3-氯吡啶 、 4-苯基咪唑 在 2-二叔丁基膦-3,4,5,6-四甲基-2′,4′,6′-三异丙基-1,1′-联苯 、 potassium phosphate 、 tris-(dibenzylideneacetone)dipalladium(0) 作用下， 以 1,4-二氧六环 、 甲苯 为溶剂， 反应 5.0h， 以89%的产率得到3-(4-phenyl-1H-imidazol-1-yl)pyridine
  参考文献：
  名称：

  完全N1选择性钯催化不对称咪唑芳基化：在尼洛替尼合成中的应用

  摘要：

  描述了不对称咪唑与芳基卤化物和三氟甲磺酸酯的完全 N(1)-选择性 Pd 催化芳基化。这项研究表明，咪唑对催化活性Pd(0)-配体配合物的原位形成具有很强的抑制作用。通过使用 Pd(2)(dba)(3) 和 L1 的预活化溶液，N-芳基化反应的效率得到了显着提高。从这些发现可以清楚地看出，虽然咪唑可以阻止 L1 与 Pd 的结合，但一旦配体与金属结合，这些杂环就不会取代它。本催化系统的实用性通过临床上重要的酪氨酸激酶抑制剂尼罗替尼的区域选择性合成得到证明。

  DOI：

  10.1021/ja2102373

文献信息

• Tandem Insertion–Cyclization Reaction of Isocyanides in the Synthesis of 1,4-Diaryl-1<i>H</i>-imidazoles: Presence of<i>N</i>-Arylformimidate Intermediate
  作者：Benjamin Pooi、Jeongbin Lee、Kyujin Choi、Hajime Hirao、Soon Hyeok Hong

  DOI：10.1021/jo501652w

  日期：2014.10.3

  A straightforward and high-yielding synthesis of 1,4-diaryl-1H-imidazoles is reported. 1,4-Diaryl-1H-imidazoels have been difficult to access in ambient conditions, but our method utilizes two different facets of isocyanide reactivity to achieve it. The reaction is believed to involve (1) NHC-copper-catalyzed isocyanide insertion into alcohol to form an N-arylformimidate intermediate and (2) subsequent base-promoted cycloaddition with benzyl isocyanide derivatives There is cooperation between these two processes through the deprotonation of benzyl isocyanide by KOtBu. The deprotonation gives tert-butyl alcohol and the benzyl isocyanide anion which are used for the first and second steps of the reaction, respectively. Various control and kinetic experiments were carried out to gain an in-depth understanding of the reaction mechanism and isocyanide reactivity. The reaction mechanism determined by density functional theory calculations was consistent with the experimental data and provided detailed explanations for the reactivity trends.
• Completely N¹-Selective Palladium-Catalyzed Arylation of Unsymmetric Imidazoles: Application to the Synthesis of Nilotinib
  作者：Satoshi Ueda、Mingjuan Su、Stephen L. Buchwald

  DOI：10.1021/ja2102373

  日期：2012.1.11

  The completely N(1)-selective Pd-catalyzed arylation of unsymmetric imidazoles with aryl halides and triflates is described. This study showed that imidazoles have a strong inhibitory effect on the in situ formation of the catalytically active Pd(0)-ligand complex. The efficacy of the N-arylation reaction was improved drastically by the use of a preactivated solution of Pd(2)(dba)(3) and L1. From these

  描述了不对称咪唑与芳基卤化物和三氟甲磺酸酯的完全 N(1)-选择性 Pd 催化芳基化。这项研究表明，咪唑对催化活性Pd(0)-配体配合物的原位形成具有很强的抑制作用。通过使用 Pd(2)(dba)(3) 和 L1 的预活化溶液，N-芳基化反应的效率得到了显着提高。从这些发现可以清楚地看出，虽然咪唑可以阻止 L1 与 Pd 的结合，但一旦配体与金属结合，这些杂环就不会取代它。本催化系统的实用性通过临床上重要的酪氨酸激酶抑制剂尼罗替尼的区域选择性合成得到证明。