2-(1-pentafluorophenyl-1H-pyrazol-3-yl)pyridine | 546142-31-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 2-(1-pentafluorophenyl-1H-pyrazol-3-yl)pyridine
• 英文别名: 2-(1-Pentafluorophenyl-1h-pyrazol-3-yl)-pyridine；2-[1-(2,3,4,5,6-pentafluorophenyl)pyrazol-3-yl]pyridine
• CAS: 546142-31-8
• 化学式: C₁₄H₆F₅N₃
• 分子量: 311.214
• InChiKey: XNEHRZTXLKVXFE-UHFFFAOYSA-N

物化性质

• 沸点：
  375.1±42.0 °C(Predicted)
• 密度：
  1.50±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  22
• 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：
  7

反应信息

• 作为反应物：
  描述：

  ammonium hexafluorophosphate 、 [iridium(III)(μ-chloro)(2-phenylpyridine)2]2 、 2-(1-pentafluorophenyl-1H-pyrazol-3-yl)pyridine 以 水 、 乙二醇 为溶剂， 以67%的产率得到[Ir(2-phenylpyridine(-1H))2(2-(1-pentafluorophenyl)-1H-pyrazol-3-yl)pyridine)]PF6
  参考文献：
  名称：

  Control of Intramolecular π–π Stacking Interaction in Cationic Iridium Complexes via Fluorination of Pendant Phenyl Rings

  摘要：

  Intramolecular pi-pi stacking interaction in one kind of phosphorescent cationic iridium complexes has been controlled through fluorination of the pendant phenyl rings on the ancillary ligands. Two blue-green-emitting cationic iridium complexes, [Ir(ppy)(2)(F2phpzpy)]PF6 (2) and [Ir(ppy)(2)(F5phpzpy)]PF6 (3), with the pendant phenyl rings on the ancillary ligands substituted with two and five fluorine atoms, respectively, have been synthesized and compared to the parent complex, [Ir(ppy)(2)(phpzpy)]PF6 (1). Here Hppy is 2-phenylpyridine, F2phpzpy is 2-(1-(3,5-difluorophenyl)-1H-pyrazol-3-yl)pyridine, F5phpzpy is 2-(1-pentafluorophenyl-1H-pyrazol-3-yl)-pyridine, and phpzpy is 2-(1-phenyl-1H-pyrazol-3-yl)pyridine. Single crystal structures reveal that the pendant phenyl rings on the ancillary ligands stack to the phenyl rings of the ppy ligands, with dihedral angles of 21 degrees, 18 degrees, and 5.0 degrees between least-squares planes for complexes 1, 2, and 3, respectively, and centroid-centroid distances of 3.75, 3.65, and 3.52 angstrom for complexes 1, 2, and 3, respectively, indicating progressively reinforced intramolecular pi-pi stacking interactions from complexes 1 to 2 and 3. Compared to complex 1, complex 3 with a significantly reinforced intramolecular face-to-face pi-pi stacking interaction exhibits a significantly enhanced (by 1 order of magnitude) photoluminescent efficiency in solution. Theoretical calculations reveal that in complex 3 it is unfavorable in energy for the pentafluorophenyl ring to swing by a large degree and the intramolecular pi-pi stacking interaction remains on the lowest triplet state.

  DOI：

  10.1021/ic2021325
• 作为产物：
  描述：

  六氟苯 、 2-(1H-吡唑-3-基)吡啶 在 potassium carbonate 作用下， 以 二甲基亚砜 为溶剂， 反应 6.0h， 以33%的产率得到2-(1-pentafluorophenyl-1H-pyrazol-3-yl)pyridine
  参考文献：
  名称：

  Control of Intramolecular π–π Stacking Interaction in Cationic Iridium Complexes via Fluorination of Pendant Phenyl Rings

  摘要：

  Intramolecular pi-pi stacking interaction in one kind of phosphorescent cationic iridium complexes has been controlled through fluorination of the pendant phenyl rings on the ancillary ligands. Two blue-green-emitting cationic iridium complexes, [Ir(ppy)(2)(F2phpzpy)]PF6 (2) and [Ir(ppy)(2)(F5phpzpy)]PF6 (3), with the pendant phenyl rings on the ancillary ligands substituted with two and five fluorine atoms, respectively, have been synthesized and compared to the parent complex, [Ir(ppy)(2)(phpzpy)]PF6 (1). Here Hppy is 2-phenylpyridine, F2phpzpy is 2-(1-(3,5-difluorophenyl)-1H-pyrazol-3-yl)pyridine, F5phpzpy is 2-(1-pentafluorophenyl-1H-pyrazol-3-yl)-pyridine, and phpzpy is 2-(1-phenyl-1H-pyrazol-3-yl)pyridine. Single crystal structures reveal that the pendant phenyl rings on the ancillary ligands stack to the phenyl rings of the ppy ligands, with dihedral angles of 21 degrees, 18 degrees, and 5.0 degrees between least-squares planes for complexes 1, 2, and 3, respectively, and centroid-centroid distances of 3.75, 3.65, and 3.52 angstrom for complexes 1, 2, and 3, respectively, indicating progressively reinforced intramolecular pi-pi stacking interactions from complexes 1 to 2 and 3. Compared to complex 1, complex 3 with a significantly reinforced intramolecular face-to-face pi-pi stacking interaction exhibits a significantly enhanced (by 1 order of magnitude) photoluminescent efficiency in solution. Theoretical calculations reveal that in complex 3 it is unfavorable in energy for the pentafluorophenyl ring to swing by a large degree and the intramolecular pi-pi stacking interaction remains on the lowest triplet state.

  DOI：

  10.1021/ic2021325

文献信息

• Heteroaryl substituted pyrazole modulators of metabotropic glutamate receptor-5
  申请人：Cosford D.P. Nicholas

  公开号：US20050026963A1

  公开（公告）日：2005-02-03

  Pyrazole compounds substituted directly, or by a bridge, with a heteroaryl moiety containing N adjacent to the point of connection of the heteroaryl, are mGluR5 modulators useful in the treatment of psychiatric and mood disorders such as, for example, schizophrenia, anxiety, depression, bipolar disorder and panic, as well as in the treatment of pain, circadian rhythm disorders, and other diseases.

  直接或通过桥连接的杂环芳基团，其中含有N相邻于杂环芳基连接点的吡唑化合物，是mGluR5调节剂，可用于治疗精神和情绪障碍，例如精神分裂症、焦虑、抑郁、双相障碍和恐慌，以及用于治疗疼痛、昼夜节律失调和其他疾病。
• HETEROARYL SUBSTITUTED PYRAZOLE MODULATORS OF METABOTROPIC GLUTAMATE RECEPTOR-5
  申请人：Merck & Co., Inc.

  公开号：EP1458383A2

  公开（公告）日：2004-09-22
• EP1458383A4
  申请人：——

  公开号：EP1458383A4

  公开（公告）日：2005-05-25
• US7569592B2
  申请人：——

  公开号：US7569592B2

  公开（公告）日：2009-08-04
• [EN] HETEROARYL SUBSTITUTED PYRAZOLE MODULATORS OF METABOTROPIC GLUTAMATE RECEPTOR-5<br/>[FR] MODULATEURS PYRAZOLE A SUBSTITUTION HETEROARYLE DU RECEPTEUR 5 METABOTROPIQUE DE GLUTAMATE
  申请人：MERCK & CO INC

  公开号：WO2003051833A2

  公开（公告）日：2003-06-26

  Pyrazole compounds substituted directly, or by a bridge, with a heteroaryl moiety containing N adjacent to the point of connection of the heteroaryl, are mGluR5 modulators useful in the treatment of psychiatric and mood disorders such as, for example, schizophrenia, anxiety, depression, bipolar disorder and panic, as well as in the treatment of pain, circadian rhythm disorders, and other diseases.