1-(3-chlorophenyl)-1H-indazol-3-amine | 1426854-88-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 1-(3-chlorophenyl)-1H-indazol-3-amine
• 英文别名: 1-(3-Chlorophenyl)indazol-3-amine；1-(3-chlorophenyl)indazol-3-amine
• CAS: 1426854-88-7
• 化学式: C₁₃H₁₀ClN₃
• 分子量: 243.695
• InChiKey: MTWGVPSINZCMSE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 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-氟苯腈 在 hydrazine hydrate 、 copper diacetate 作用下， 以 甲醇 、 乙醇 为溶剂， 反应 24.0h， 生成 1-(3-chlorophenyl)-1H-indazol-3-amine
  参考文献：
  名称：

  铜催化的C-氨基-NH-唑的连续N-芳基化反应。

  摘要：

  铜（II）催化的硼酸促进的CN键交叉偶联反应已成功开发，可用于C-氨基-NH-唑的连续N-芳基化反应。这些通用方案可与多种芳基/杂芳基硼酸兼容，并能以两步顺序或一锅快速访问各种二芳基氨基唑衍生物。

  DOI：

  10.1039/c4cc05628k

文献信息

• Rapid access to 3-aminoindazoles from nitriles with hydrazines: a strategy to overcome the basicity barrier imparted by hydrazines
  作者：Chunyan Zhang、Haowen Zhao、Zehua Li、Zuyu Liang、Shuo Qi、Mingyu Cai、Sheng Zhang、Xiaofei Jia、Guoying Zhang、Mao-Lin Hu

  DOI：10.1039/d0cc03789c

  日期：——

  A practical and efficient base mediated synthesis of free 3-aminoindazoles has been developed from the reaction of nitriles with hydrazines, which successfully overcomes the difficulty of using aromatic hydrazines as substrates and allows for the synthesis of a wide range of N-aryl substituted free 3-aminoindazoles in moderate to excellent yields under mild conditions in one-pot. This finding provides

  从腈与肼的反应中开发出了一种实用，有效的碱介导的游离3-氨基吲唑合成方法，该方法成功克服了使用芳香族肼作为底物的困难，并可以合成多种N-芳基取代的游离3 -氨基吲唑在温和条件下一锅即可获得中等至极佳的收率。这一发现为合成各种功能化的3-氨基吲唑衍生物提供了一种快速而有用的策略。
• 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.
• 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
• 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.