3-(4-chlorophenyl)-1-phenyl-1H-indazole | 51112-92-6

• 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-chlorophenyl)-1-phenyl-1H-indazole
• 英文别名: 3-(4-Chlorophenyl)-1-phenylindazole；3-(4-chlorophenyl)-1-phenylindazole
• CAS: 51112-92-6
• 化学式: C₁₉H₁₃ClN₂
• 分子量: 304.779
• InChiKey: WIORXVVOMXIGHV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  22
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  17.8
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  吲唑 在 copper(l) iodide 、 1,10-菲罗啉 、 palladium diacetate 、 potassium carbonate 作用下， 以 N,N-二甲基乙酰胺 为溶剂， 反应 48.75h， 生成 3-(4-chlorophenyl)-1-phenyl-1H-indazole
  参考文献：
  名称：

  1H-吲唑的直接C-3-芳基化

  摘要：

  报道了取代的 1H-吲唑的分子间 C-H 芳基化的第一个例子。各种 1-取代的吲唑被用作原料，（杂）芳基溴化物和碘化物作为偶联伙伴进行了研究。研究了不同的反应条件。使用 Pd(OAc)2 作为催化剂，1,10-菲咯啉作为配体，K2CO3 作为碱，DMA 作为溶剂获得了最好的结果。配体对取代的 1H-吲唑的 C-H 芳基化的关键作用得到强调。

  DOI：

  10.1002/ejoc.201200860

文献信息

• Divergent Synthesis of 1<i>H</i>-Indazoles and 1<i>H</i>-Pyrazoles from Hydrazones<i>via</i>Iodine-Mediated Intramolecular Aryl and<i>sp</i>³C-H Amination
  作者：Wei Wei、Zhen Wang、Xikang Yang、Wenquan Yu、Junbiao Chang

  DOI：10.1002/adsc.201700824

  日期：2017.10.4

  by condensation of hydrazines with the corresponding ketones. In the presence of potassium iodide, I2-mediated oxidative cyclization of diaryl and tert-butyl aryl ketone hydrazones produced 1H-indazoles via direct aryl C–H amination. Under similar reaction conditions, primary and secondary alkyl ketone hydrazones were transformed into 1H-pyrazole products in a reaction involving sp3 C–H amination. This

  molecular原子的分子内CH胺的发散已被开发出来，采用分子碘（I 2）作为唯一氧化剂。通过肼与相应的酮的缩合可以容易地获得所需的底物。在碘化钾存在下，二芳基和叔丁基芳基酮aryl的I 2介导的氧化环化反应通过直接芳基CH胺化反应生成1 H-吲唑。在相似的反应条件下，伯和仲烷基酮在涉及sp 3的反应中转化为1 H-吡唑产物。C–H胺化。这种合成方法不涉及过渡金属，并且操作简单，可以高效，可扩展地轻松获得吲唑和吡唑衍生物。
• Synthesis of Indazoles and Azaindazoles by Intramolecular Aerobic Oxidative CN Coupling under Transition-Metal-Free Conditions
  作者：Jiantao Hu、Huacheng Xu、Pengju Nie、Xiaobo Xie、Zongxiu Nie、Yu Rao

  DOI：10.1002/chem.201304923

  日期：2014.4.1

  A transition‐metal‐free oxidative CN coupling method has been developed for the synthesis of 1H‐azaindazoles and 1H‐indazoles from easily accessible hydrazones. The procedure uses TEMPO, a basic additive, and dioxygen gas as the terminal oxidant. This reaction demonstrates better reactivity, functional group tolerance, and broader scope than comparable metal catalyzed reactions.

  过渡金属-自由氧化Ç  N个耦合方法已为1的合成开发ħ -azaindazoles 1个ħ从容易获得腙-indazoles。该程序使用TEMPO（一种碱性添加剂）和双氧气体作为终端氧化剂。与可比的金属催化反应相比，该反应显示出更好的反应性，官能团耐受性和更宽的范围。
• [Bis-(trifluoroacetoxy)iodo]benzene-Mediated Oxidative Direct Amination C-N Bond Formation: Synthesis of 1<i>H</i>-Indazoles
  作者：Zhiguo Zhang、Yuanyuan Huang、Guoqing Huang、Guisheng Zhang、Qingfeng Liu

  DOI：10.1002/jhet.2839

  日期：2017.7

  An efficient [bis‐(trifluoroacetoxy)iodo]benzene (PIFA)‐mediated oxidative C‐N bond formation is developed for the synthesis of 1H‐indazoles from readily available arylhydrazones. The reaction tolerates a wide range of functional groups and has broad scope of substrates. Moreover, this method is a relative green and reliable method for rapid preparation of substituted 1H‐indazoles under mild conditions

  已开发出一种有效的[双（三氟乙酰氧基）碘]苯（PIFA）介导的氧化性C-N键形成，用于从易得的芳基hydr酮合成1 H-吲唑。该反应可耐受各种官能团并且具有广泛的底物范围。此外，该方法是在温和条件下快速制备取代的1 H-吲唑的相对绿色可靠方法。
• Copper-Catalyzed Aerobic C(sp²)–H Functionalization for C–N Bond Formation: Synthesis of Pyrazoles and Indazoles
  作者：Xianwei Li、Li He、Huoji Chen、Wanqing Wu、Huanfeng Jiang

  DOI：10.1021/jo400162d

  日期：2013.4.19

  A simple, practical, and highly efficient synthesis of pyrazoles and indazoles via copper-catalyzed direct aerobic oxidative C(sp2)–H amination has been reported herein. This process tolerated a variety of functional groups under mild conditions. Further diversification of pyrazoles was also investigated, which provided its potential for drug discovery.

  本文报道了通过铜催化的直接好氧氧化C（sp 2）-H胺的合成简单，实用，高效的吡唑和吲唑合成方法。在温和条件下，该过程可耐受各种官能团。还研究了吡唑的进一步多样化，这为其药物发现提供了潜力。
• Pd- and Cu-catalyzed C–H arylation of indazoles
  作者：Keika Hattori、Kazuya Yamaguchi、Junichiro Yamaguchi、Kenichiro Itami

  DOI：10.1016/j.tet.2012.05.091

  日期：2012.9

  The palladium- and copper-catalyzed C-H arylation reactions of 1H- and 2H-indazoles with haloarenes are described. A PdCl2/phen/Ag2CO3/K3PO4 catalytic system is effective for the C-H arylation of 1H- and 2H-indazoles with haloarenes, whereas a less expensive CuI/phen/LiOt-Bu catalytic system is applicable to the C H coupling of substituted 2H-indazoles and iodoarenes. The utility of newly developed catalyst was demonstrated in the rapid synthesis of YC-1 (an antitumor agent) and YD-3 (platelet anti-aggregating agent). These new reactions represent important direct functionalization tools of indazoles, well-known bioisosteres of pharmaceutically important indole core. (C) 2012 Elsevier Ltd. All rights reserved.