3-phenyl-1-(p-tolyl)-1H-indazole | 1419611-76-9

• 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-phenyl-1-(p-tolyl)-1H-indazole
• 英文别名: 1-(4-Methylphenyl)-3-phenylindazole；1-(4-methylphenyl)-3-phenylindazole
• CAS: 1419611-76-9
• 化学式: C₂₀H₁₆N₂
• 分子量: 284.36
• InChiKey: VZKJDGMZDZPRKO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  22
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.05
• 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：

  N-(4-methylphenyl) benzophenone hydrazone 在 [双(三氟乙酰氧基)碘]苯 作用下， 反应 0.08h， 以71%的产率得到3-phenyl-1-(p-tolyl)-1H-indazole
  参考文献：
  名称：

  [双（三氟乙酰氧基）碘]苯介导的氧化性直接胺化CN键形成：1H-吲唑的合成

  摘要：

  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。

  DOI：

  10.1002/jhet.2839

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 1<i>H</i>-indazoles by an electrochemical radical C_sp²–H/N–H cyclization of arylhydrazones
  作者：Hao Wan、Dongting Li、Huadan Xia、Liwen Yang、Hesham Alhumade、Hong Yi、Aiwen Lei

  DOI：10.1039/d1cc04656j

  日期：——

  bond-forming reactions to N-heterocyclic frameworks has been a long-standing interest in organic synthesis. In this work, we develop an electrochemical radical Csp2–H/N–H cyclization of arylhydrazones to 1H-indazoles. The electrochemical anodic oxidation approach was adopted to synthesize a variety of 1H-indazole derivatives in moderate to good yields. HFIP was not only employed as a solvent or the proton donor

  对 N-杂环骨架进行高效且可持续的 C-N 键形成反应一直是有机合成领域的长期兴趣。在这项工作中，我们开发了芳基腙到 1 H-吲唑的电化学自由基 C sp 2 -H/N-H 环化。采用电化学阳极氧化方法合成了多种1 H-吲唑衍生物，产率中等至较好。HFIP不仅用作溶剂或质子供体，而且可以促进N自由基的形成。这种合成方法操作简单，较便宜的电极适用于这种化学。
• Electrochemical dehydrogenative C–N coupling of hydrazones for the synthesis of 1<i>H</i>-indazoles
  作者：Hong Zhang、Zenghui Ye、Na Chen、Zhenkun Chen、Fengzhi Zhang

  DOI：10.1039/d1gc04534b

  日期：——

  An electrochemical dehydrogenative C–N coupling method has been developed for the synthesis of 1H-indazoles from easily available hydrazones. Various functional groups are compatible with this metal- and oxidant-free protocol which can be carried out on a gram-scale under neutral and mild conditions. This method was applied for the efficient synthesis of anti-tumor compounds. Mechanism studies show

  已经开发了一种电化学脱氢 C-N 偶联方法，用于从容易获得的腙合成 1 H-吲唑。各种官能团与这种不含金属和氧化剂的协议兼容，可以在中性和温和条件下以克级进行。该方法可用于高效合成抗肿瘤化合物。机制研究表明，HFIP 在这一转变中发挥着重要作用，可能涉及一种激进的途径。
• Divergent strategy for the chemoselective synthesis of N-Arylbenzimidazoles and N-Arylindazoles from arylamino oximes
  作者：Zhen-Hua Li、Xiao-Meng Sun、Jin-Jing Qin、Zhi-Yong Tan、Wen-Biao Wang、Yao Ma

  DOI：10.1016/j.tet.2020.130945

  日期：2020.2

  An efficient and divergent synthesis of N-arylbenzimidazoles and N-arylindazoles from arylamino oximes based on reaction conditions selection was developed. The synthesis was approached by treating oximes with BTC and the chemoselectivity was regulated by the amount of Et3N. This switchable N-N and N-C bond formation process features mild reaction conditions, simple execution, high chemoselectivity and broad substrate scope. (C) 2020 Elsevier Ltd. All rights reserved.
• An efficient transition-metal-free synthesis of 1H-indazoles from arylhydrazones with montmorillonite K-10 under O2 atmosphere
  作者：Jin Yu、Jin Woo Lim、Su Yeon Kim、Jimin Kim、Jae Nyoung Kim

  DOI：10.1016/j.tetlet.2015.01.183

  日期：2015.3

  An efficient transition-metal-free synthetic method of 1H-indazoles has been developed. The reaction of arylhydrazones in the presence of montmorillonite K-10 in 1,2-dichlorobenzene at 130 degrees C afforded 1Hindazoles in good yields most likely via a sequential intramolecular nucleophilic cyclization and an aerobic oxidation pathway. (C) 2015 Elsevier Ltd. All rights reserved.