2-phenyl-3-(4-fluorophenyl)-2H-indazole | 1421276-39-2

• 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-phenyl-3-(4-fluorophenyl)-2H-indazole
• 英文别名: 3-(4-fluorophenyl)-2-phenyl-2H-indazole
• CAS: 1421276-39-2
• 化学式: C₁₉H₁₃FN₂
• 分子量: 288.324
• InChiKey: YYLMDUFTIXKQFM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.83
• 重原子数：
  22.0
• 可旋转键数：
  2.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  17.82
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为产物：
  描述：

  邻溴苯甲醛 在 copper(l) iodide 、 sodium azide 、 四甲基乙二胺 、 potassium tert-butylate 作用下， 以 二甲基亚砜 为溶剂， 反应 48.5h， 生成 2-phenyl-3-(4-fluorophenyl)-2H-indazole
  参考文献：
  名称：

  Catalyst-free photoarylation of 2-aryl-2H-indazoles by carbon–iodine bond activation

  摘要：

  A catalyst-free photoarylation of 2-aryl-2H-indazoles by carbon–iodine bond activation has been developed for the synthesis of C3-arylated indazoles in moderate to good yields.

  DOI：

  10.1039/d4ob00820k

文献信息

• Rhenium-Catalyzed [4 + 1] Annulation of Azobenzenes and Aldehydes via Isolable Cyclic Rhenium(I) Complexes
  作者：Xiaoyu Geng、Congyang Wang

  DOI：10.1021/acs.orglett.5b00938

  日期：2015.5.15

  The first Re-catalyzed [4 + 1] annulation of azobenzenes with aldehydes was developed to furnish 2H-indazoles via isolable and characterized cyclic ReI-complexes. For the first time, the acetate-acceleration effect is showcased in Re-catalyzed C–H activation reactions. Remarkably, mechanistic studies revealed an irreversible aldehyde-insertion step, which is in sharp contrast to those of previous Rh-

  首次开发了用醛对偶氮苯进行再催化的[4 +1]环合反应，以通过可分离和表征的环状Re I-络合物提供2 H-吲唑。在重新催化的C–H活化反应中，乙酸促进作用首次显示出来。值得注意的是，机理研究表明，醛的插入步骤不可逆，这与以前的Rh和Co体系的形成强烈反差。
• Metal-free, regioselective, visible light activation of 4CzIPN for the arylation of 2<i>H</i>-indazole derivatives
  作者：Rajendhiran Saritha、Sesuraj Babiola Annes、Subburethinam Ramesh

  DOI：10.1039/d1ra02372a

  日期：——

  Highly regioselective organo photocatalysis of 4CzIPN (1,2,3,5-tetrakis(carbazol-9-yl)-4,6-dicyanobenzene) for the arylation of 2H-indazole is demonstrated.

  4CzIPN（1,2,3,5-四(咔唑-9-基)-4,6-二氰基苯）的高区域选择性有机光催化剂用于2H-吲哚的芳基化反应。
• Visible-light-mediated direct C3-arylation of 2<i>H</i>-indazoles enabled by an electron-donor–acceptor complex
  作者：Kim Christopher C. Aganda、Junyoung Kim、Anna Lee

  DOI：10.1039/c9ob02074h

  日期：——

  A mild visible-light-mediated, photocatalyst-free arylation of 2H-indazoles was developed. The formation of an electron donor–acceptor complex by 2H-indazoles and aryl diazonium salts in the presence of pyridine allows the direct arylation of 2H-indazoles under visible-light irradiation. This process provides an efficient route for the synthesis of C3-arylated-2H-indazoles, which are important scaffolds

  开发了温和的可见光介导的2 H-吲唑无芳基芳基化反应。在吡啶存在下，2 H-吲唑和芳基重氮盐形成电子供体-受体配合物，使2 H-吲唑在可见光照射下直接芳基化。该方法为合成C 3-芳基化的2 H-吲唑提供了有效的途径，C 3-芳基化的2 H-吲唑是各种生物活性化合物的重要支架。
• Rh(III)-Catalyzed [4 + 1]-Annulation of Azoxy Compounds with Alkynes: A Regioselective Approach to 2<i>H</i>-Indazoles
  作者：Zhen Long、Yudong Yang、Jingsong You

  DOI：10.1021/acs.orglett.7b00982

  日期：2017.6.2

  A rhodium-catalyzed regioselective C–H activation/cyclization of azoxy compounds with alkynes has been disclosed to construct a variety of 2H-indazoles. A [4 + 1]-cycloaddition rather than a normal [4 + 2] mode is observed in the process of cyclative capture along with an oxygen-atom transfer and a C≡C triple bond cleavage. This protocol features a broad substrate scope, a good functional group tolerance

  铑催化炔烃对偶氮化合物的区域选择性C–H活化/环化反应已被证实可构建多种2 H-吲唑。在循环捕获的过程中观察到[4 +1]-环加成而不是正常的[4 +1]模式，以及氧原子转移和C≡C三键裂解。该协议具有广泛的底物范围，良好的官能团耐受性和独特的区域选择性。
• Visible-Light-Promoted Metal-Free 3-Arylation of 2-Aryl-2H-­indazoles with Triarylsulfonium Salts
  作者：Kai Sun、Bing Yu、Anzai Shi、Panjie Xiang、Yanxuan Wu、Chang Ge、Yan Liu

  DOI：10.1055/a-1938-9550

  日期：2023.3

  An efficient approach for the photosynthesis of various arylated 2-aryl-2H-indazoles (38 examples) in moderate to good yields (up to 87% yield) under mild conditions was developed by employing 1,2,3,5-tetrakis(carbazol-9-yl)-4,6-dicyanobenzene (4CzIPN) as an inexpensive photocatalyst. This protocol features wide substrate scope, good functional group tolerance, and operational simplicity. In addition

  通过采用1,2,3,5-四 ( carbazol-9-yl)-4,6-dicyanobenzo (4CzIPN) 作为一种廉价的光催化剂。该协议具有广泛的底物范围、良好的功能组耐受性和操作简单性。此外，该策略成功应用于药物分子的后期修饰，首次实现了将复杂药物有意义地引入2H-吲唑骨架。