3-Methyl-1-p-Nitrophenylindazol | 4106-21-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 3-Methyl-1-p-Nitrophenylindazol
• 英文别名: 3-Methyl-1-(4-nitro-phenyl)-1H-indazole；3-methyl-1-(4-nitrophenyl)indazole
• CAS: 4106-21-2
• 化学式: C₁₄H₁₁N₃O₂
• 分子量: 253.26
• InChiKey: MBGUVMHLWAERHO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  19
• 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：
  63.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2-(4'-nitroanilino)acetophenone 在 三光气 、 盐酸羟胺 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 生成 3-Methyl-1-p-Nitrophenylindazol
  参考文献：
  名称：

  Divergent strategy for the chemoselective synthesis of N-Arylbenzimidazoles and N-Arylindazoles from arylamino oximes

  摘要：

  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.

  DOI：

  10.1016/j.tet.2020.130945

文献信息

• Assembly of <i>N</i>,<i>N</i>-Disubstituted Hydrazines and 1-Aryl-1<i>H</i>-indazoles via Copper-Catalyzed Coupling Reactions
  作者：Xiaodong Xiong、Yongwen Jiang、Dawei Ma

  DOI：10.1021/ol300847v

  日期：2012.5.18

  CuI-catalyzed coupling of N-acyl-N′-substituted hydrazines with aryl iodides takes place at 60–90 °C to afford N-acyl-N′,N′-disubstituted hydrazines regioselectively and thereby gives a facile method for assembling N,N-diaryl hydrazines. N-Acyl-N′-substituted hydrazines can also react with 2-bromoarylcarbonylic compounds at 60–125 °C under the catalysis of CuI/4-hydroxy-l-proline to provide 1-aryl-1H-indazoles

  N-酰基-N'-取代的肼与芳基碘化物的CuI催化偶联在60-90°C下进行，可选择性地提供N-酰基-N '，N'-双取代的肼，从而提供了一种简便的组装N的方法，N-二芳基肼。在CuI / 4-羟基-1-脯氨酸的催化下，N-酰基-N'-取代的肼还可在60-125°C下与2-溴芳基羰基化合物反应，生成1-芳基-1 H-吲唑。
• METHOD OF SYNTHESIZING 1H-INDAZOLE COMPOUNDS
  申请人：Stambuli James P.

  公开号：US20100056800A1

  公开（公告）日：2010-03-04

  A method is provided for synthesizing 1H-indazole compounds in which aromatic carbonyl compounds are reacted with a nitrogen source to form oximes which are then converted to 1H-indazoles.

  提供了一种合成1H-吲唑化合物的方法，其中芳香酮化合物与氮源反应形成肟类，然后转化为1H-吲唑。
• Synthesis of <i>N</i>-Arylindazoles and Benzimidazoles from a Common Intermediate
  作者：Brenda C. Wray、James P. Stambuli

  DOI：10.1021/ol101899q

  日期：2010.10.15

  A variety of N-aryl-1H-indazoles and benzimidazoles were synthesized from common arylamino oximes in good to excellent yields The product selectivity depends upon the base used in the reaction, as triethylamine promoted the formation of benzimidazoles, whereas 2-aminopyridine promoted the formation of N-arylindazoles This method is valuable to the synthetic community because both indazoles and benzimidazoles are prevalent in pharmaceuticals
• US8022227B2
  申请人：——

  公开号：US8022227B2

  公开（公告）日：2011-09-20
• 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.