7-phenylpyrazolo[1,5-a]pyridine | 319432-24-1

• 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: 7-phenylpyrazolo[1,5-a]pyridine
• CAS: 319432-24-1
• 化学式: C₁₃H₁₀N₂
• 分子量: 194.236
• InChiKey: VVIPHSVCRUQLJS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  17.3
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  7-phenylpyrazolo[1,5-a]pyridine 在 palladium(II) trifluoroacetate 、 copper diacetate 作用下， 以 二甲基亚砜 为溶剂， 反应 15.0h， 以64%的产率得到7,7'-diphenyl-3,3'-bipyrazolo[1,5-a]pyridine
  参考文献：
  名称：

  钯催化吡唑并[1,5-a]吡啶的交叉脱氢偶联合成双吡唑[1,5-a]吡啶及其机理研究

  摘要：

  本文介绍了通过吡唑并[1,5- a ]吡啶前体的直接交叉脱氢偶联合成一系列3,3'-联吡唑并[1,5- a ]吡啶衍生物。这种涉及钯 (II) 催化的 C-H 键活化的简单有效的方法显示出良好的官能团耐受性和产品收率（高达 94%）。通过从动力学同位素效应实验研究和密度泛函理论计算中获得的机理见解，概述了合理的反应机理。此外，生成的 7,7'-diaryl-3,3'-bipyrazolo[1,5- a ]pyridines 的后续衍生化，通过钯介导的邻C-H 键活化，然后是高价碘诱导的氯化，使这一系列化合物具有更多的扩展 π 共轭和扭曲的构象。我们对这些双吡唑并[1,5 - a ]吡啶基发光剂的研究为定制有机发光材料提供了新的机会。

  DOI：

  10.1021/acs.joc.2c00895
• 作为产物：
  描述：

  7-(Tributylstannyl)pyrazolo[1,5-a]pyridine 在 四(三苯基膦)钯 碘 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 4.0h， 生成 7-phenylpyrazolo[1,5-a]pyridine
  参考文献：
  名称：

  Effective and Variable Functionalization of Pyrazolo[1,5-a]pyridines Involving Palladium-Catalyzed Coupling Reactions

  摘要：

  通过钯催化的交叉偶联反应，合成了多种7位取代的吡唑并[1,5-a]吡啶。从相应的7-碘衍生物出发，成功引入了苯基、乙烯基、乙炔基、氰基和氨基。在Negishi条件下，吡唑并[1,5-a]吡啶-7-基锌碘可以反应生成偶联产物16。

  DOI：

  10.1055/s-2000-8215

文献信息

• METHOD FOR PRODUCING PYRAZOLE FUSED RING DERIVATIVE
  申请人：Eisai R&D Management Co., Ltd.

  公开号：EP2202233A1

  公开（公告）日：2010-06-30

  Disclosed is a commercially advantageous method for producing a pyrazole fused ring derivative (such as a 7-phenylpyrazolo[1,5-a]pyridine derivative). Specifically disclosed is a method for producing a compound (I) represented by the formula (I) below or a salt thereof, which comprises a step A wherein a hydroxy group in a compound (IV) represented by the formula (IV) below is converted into a methoxy group, thereby obtaining a compound (I) or a salt thereof:

  揭示了一种生产吡唑融合环衍生物（如7-苯基吡唑并[1,5-a]吡啶衍生物）的商业上有利的方法。具体揭示了一种生产由下式（I）表示的化合物（I）或其盐的方法，其中包括步骤A，其中将由下式（IV）表示的化合物（IV）中的羟基转化为甲氧基，从而获得化合物（I）或其盐：
• Process for production of pyrazole-fused ring derivatives
  申请人：Negi Shigeto

  公开号：US20070191613A1

  公开（公告）日：2007-08-16

  An object of the invention is to find out intermediates usful for the synthesis of pyrazol-fused ring derivatives (such as 7-phenylpyrazolo[1,5-a]pyridine derivatives) and a method for producing the same. A method for producing compound represented by the general formula (II), wherein Z 1 and Z 2 each independently represents a methine group or a nitrogen atom; R 1 represents an ethyl group or the like; R 5 represents a hydrogen atom or the like; R 2 and R 3 each independently represents a C 1-6 alkyl group or the like, salts thereof, or solvates of both, comprising the step of: reacting a compound represented by the general formula (I), wherein Z 1 , Z 2 , R 5 , R 1 , R 2 and R 3 each has the same definition as described above, with an organometallic reagent; and then reacting the resulting product with pentafluoroiodobenzene.

  本发明的目的是找出用于合成吡唑融合环衍生物（例如7-苯基吡唑并[1,5-a]吡啶衍生物）的中间体以及生产方法。一种生产通用式（II）所代表的化合物的方法，其中Z1和Z2分别独立表示亚甲基基团或氮原子；R1表示乙基基团或类似物；R5表示氢原子或类似物；R2和R3分别独立表示C1-6烷基基团或类似物，它们的盐或两者的溶剂，包括以下步骤：将通用式（I）所代表的化合物与有机金属试剂反应；然后将所得产物与五氟化碘苯反应。
• Novel bipyrazolo[1,5-<i>a</i>]pyridine luminogens with aggregation-induced emission enhancement properties
  作者：Pu-Yen Hsiao、Jean-Ho Chu

  DOI：10.1039/d1cc05371j

  日期：——

  A novel 3,3′-bipyrazolo[1,5-a]pyridine molecular scaffold was obtained as a product of serendipity. Both photophysical characterisations and HOMO–LUMO theoretical calculations indicate its potential as a promising fluorophore with notable intramolecular charge transfer. Nonetheless, the emission properties of this compound suffer from the typical aggregation-caused quenching effect. To overcome this

  作为偶然的产物，获得了一种新型 3,3'-联吡唑并[1,5- a ] 吡啶分子支架。光物理表征和 HOMO-LUMO 理论计算表明其作为具有显着分子内电荷转移的有前途的荧光团的潜力。尽管如此，这种化合物的发射特性会受到典型的聚集引起的猝灭效应的影响。为了克服这种情况，我们在骨架上引入了额外的二芳基，并通过钯催化的分子间 C–H/C–合成了一系列 7,7'-二芳基-3,3'-联吡唑并[1,5- a ]吡啶H 键交叉偶联反应的产率为 35-62%。这一系列具有扭曲 π 结构的定制发光体显示出聚集诱导的发射增强特性。
• Palladium-Catalyzed Regioselective Arylation of Pyrazolo[1,5-<i>a</i>]pyridines via C–H Activation and Synthetic Applications on P38 Kinase Inhibitors
  作者：Hung-Chou Wu、Jean-Ho Chu、Chin-Wei Li、Long-Chih Hwang、Ming-Jung Wu

  DOI：10.1021/acs.organomet.5b00988

  日期：2016.1.25

  A direct arylation of pyrazolo[1,5-a]pyridines with aryl iodides selectively occurring at the C-3 and C-7 positions via palladium-catalyzed C-H activation is described. In these reactions, (a) cesium(I) fluoride and (b) silver(I) carbonate were employed as the additive to afford 3- and 7-arylated pyrazolo[1,5-a]pyridines, respectively, in modest to good yields. These reactions showed good compatibility with functional groups, and the catalytic mechanisms of these reactions were proposed. Finally, the synthetic application on the potent p38 kinase inhibitors was demonstrated.
• Di- and trisubstituted pyrazolo[1,5-a]pyridine derivatives: synthesis, dopamine receptor binding and ligand efficacy
  作者：Stefan Löber、Tarek Aboul-Fadl、Harald Hübner、Peter Gmeiner

  DOI：10.1016/s0960-894x(01)00814-9

  日期：2002.2

  Based on the lead molecule FAUC 113, a series of di- and trisubstituted pyrazolo[1,5-a]pyridine derivatives was synthesized and investigated for their dopamine receptor binding profile. The carbonitrile 11a (FAUC 327) showed excellent pharmacological properties combining high D4 affinity (K-i = 1.5 nM) and selectivity with significant intrinsic activity (31%) in low nanomolar concentrations (EC50 = 1.5 nM), (C) 2002 Elsevier Science Ltd. All rights reserved.