1-对甲苯基-1H-吲唑-3-胺 | 1426854-86-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 中文名称: 1-对甲苯基-1H-吲唑-3-胺
• 英文名称: 1-(p-tolyl)-1H-indazol-3-amine
• 英文别名: 1-p-tolyl-1H-indazol-3-amine；1-(4-methylphenyl)indazol-3-amine
• CAS: 1426854-86-5
• 化学式: C₁₄H₁₃N₃
• 分子量: 223.277
• InChiKey: TZSZIIRZDQLKRP-UHFFFAOYSA-N

物化性质

• 沸点：
  346.0±35.0 °C(Predicted)
• 密度：
  1.21±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  43.8
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  2-溴-N-羟基苯甲酰胺 在 sodium methylate 、 copper diacetate 、 potassium carbonate 作用下， 以 甲醇 、 乙醇 、 N,N-二甲基乙酰胺 为溶剂， 反应 4.17h， 生成 1-对甲苯基-1H-吲唑-3-胺
  参考文献：
  名称：

  Cascade Synthesis of Kinase-Privileged 3-Aminoindazoles via Intramolecular N–N Bond Formation

  摘要：

  DOI：

  10.1021/acs.joc.1c03057

文献信息

• Copper immobilized at a covalent organic framework: an efficient and recyclable heterogeneous catalyst for the Chan–Lam coupling reaction of aryl boronic acids and amines
  作者：Yi Han、Mo Zhang、Ya-Qing Zhang、Zhan-Hui Zhang

  DOI：10.1039/c8gc02611d

  日期：——

  inexpensive reagents and was employed as an effective support for heterogeneous copper. It was demonstrated that the obtained Cu@PI-COF is a highly active heterogeneous catalyst which can effectively promote the Chan–Lam coupling reaction of aryl boronic acids and amines in an open flask without the aid of any base or additive. In addition, the catalyst could be readily recovered from the reaction mixture

  具有高热稳定性和化学稳定性的聚酰亚胺共价有机骨架（PI-COF）可以很容易地从市售和廉价的试剂中制备，并被用作异质铜的有效载体。结果表明，所获得的Cu @ PI-COF是一种高活性的非均相催化剂，可以在不使用任何碱或添加剂的情况下，有效地促进开放烧瓶中芳基硼酸和胺的Chan-Lam偶联反应。另外，可以通过简单的过滤容易地从反应混合物中回收催化剂，并重复使用至少八个循环，而没有结构和催化活性的任何可观察到的变化。
• Copper‐Catalyzed <i>N</i> ¹ Coupling of 3‐Aminoindazoles and Related Aminoazoles with Aryl Bromides
  作者：Patrick Cyr、Eve‐Marline Joseph‐Valcin、Patrick Boissarie、Bruno Simoneau、Anne Marinier

  DOI：10.1002/ejoc.202101245

  日期：2022.1.27

  AbstractThe N1‐selective arylation of 3‐aminoindazoles using copper catalysis is herein reported. The reaction uses readily accessible aryl bromides as coupling partners, including those from heterocycles, and allows easy access to a broad variety of substituted 3‐aminoindazoles. The methodology was also examined on other aminoazoles of interest for the pharmaceutical industry.
• Assembly of Substituted 3-Aminoindazoles from 2-Bromobenzonitrile via a CuBr-Catalyzed Coupling/Condensation Cascade Process
  作者：Lanting Xu、Yinsheng Peng、Qiangbiao Pan、Yongwen Jiang、Dawei Ma

  DOI：10.1021/jo400071h

  日期：2013.4.5

  CuBr-catalyzed coupling reaction of 2-halobenzonitriles with hydrazine carboxylic esters and CuBr/4-hydroxy-L-proline-catalyzed coupling reaction of 2-bromobenzonitriles with N'-arylbenzohydrazides proceed smoothly at 60-90 degrees C to provide substituted 3-aminoindazoles through a cascade coupling/condensation (or coupling/deacylation/condensation) process. A wide range of 3-aminoindazoles with substituents at both the 1-position and the phenyl ring part can be prepared from the corresponding coupling partners.
• Cascade Synthesis of Kinase-Privileged 3-Aminoindazoles via Intramolecular N–N Bond Formation
  作者：W. Felix Zhu、Andreas Krämer、Stefan Knapp、Ewgenij Proschak、Victor Hernandez-Olmos

  DOI：10.1021/acs.joc.1c03057

  日期：2022.3.4