3-(3-nitrophenyl)-1H-indazole | 1310207-69-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡唑类
• 英文名称: 3-(3-nitrophenyl)-1H-indazole
• CAS: 1310207-69-2
• 化学式: C₁₃H₉N₃O₂
• 分子量: 239.233
• InChiKey: CRVLYIIAMMNHRI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  18
• 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：
  74.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  diisopropyl 1-(2-(3-nitrobenzoyl)phenyl)hydrazine-1,2-dicarboxylate 在 盐酸 作用下， 以 N,N-二甲基乙酰胺 、 水 为溶剂， 反应 16.0h， 以19%的产率得到3-(3-nitrophenyl)-1H-indazole
  参考文献：
  名称：

  A facile route to 1H- and 2H-indazoles from readily accessible acyl hydrazides by exploiting a novel aryne-based molecular rearrangement

  摘要：

  一种简便的将易得的酰基肼转化为1H和2H-吲唑的程序，通过一种基于新颖芳炔的分子重排途径。

  DOI：

  10.1039/c8cc06556j

文献信息

• Design and Application of New Imidazolylsulfonate-Based Benzyne Precursor: An Efficient Triflate Alternative
  作者：Szabolcs Kovács、Ádám I. Csincsi、Tibor Zs. Nagy、Sándor Boros、Géza Timári、Zoltán Novák

  DOI：10.1021/ol300529j

  日期：2012.4.20

  cycloadditions involving benzyne intermediates. The precursor offers an efficient alternative for generating benzynes compared to widely used ortho TMS triflates under similar reaction conditions. With the utilization of this new precursor, the formation of potentially genotoxic trifluoromethanesulfonate side product is eliminated. The applicability of the new benzyne precursor was demonstrated in different

  几种邻-（三甲基甲硅烷基）芳基咪唑基磺酸盐可以通过简单的方法合成，并成功地用于涉及苯炔中间体的环加成反应中。与在相似反应条件下广泛使用的邻位TMS三氟甲磺酸酯相比，该前体提供了生成苯炔的有效替代方法。通过使用这种新的前体，消除了潜在的具有遗传毒性的三氟甲磺酸盐副产物的形成。新型苯并炔前体的适用性已在不同类型的环加成反应制备杂环分子中得到证明。
• Synthesis of 3-Substituted Indazoles from Arynes and <i>N</i>-Tosylhydrazones
  作者：Pan Li、Jingjing Zhao、Chunrui Wu、Richard C. Larock、Feng Shi

  DOI：10.1021/ol201086g

  日期：2011.7.1

  Readily available, stable, and inexpensive N-tosylhydrazones react with arynes under mild reaction conditions to afford 3-substituted indazoles in moderate to good yields. The reaction appears to involve a dipolar cycloaddition of in situ generated diazo compounds and arynes.
• Synthesis of Substituted 1<i>H</i>-Indazoles from Arynes and Hydrazones
  作者：Pan Li、Chunrui Wu、Jingjing Zhao、Donald C. Rogness、Feng Shi

  DOI：10.1021/jo202598e

  日期：2012.4.6

  The 1H-indazole skeleton can be constructed by a [3 + 2] annulation approach from arynes and hydrazones. Under different reaction conditions, both N-tosylhydrazones and N-aryl/alkylhydrazones can be used to afford a variety of indazoles. The former reaction affords 3-substituted indazoles either via in situ generated diazo compounds or through an annulation/elimination process. The latter reaction leads to 1,3-disubstituted indazoles likely through an annulation/oxidation process. The reactions operate under mild conditions and can accommodate aryl, vinyl, and less satisfactorily, alkyl groups.
• A facile route to 1<i>H</i>- and 2<i>H</i>-indazoles from readily accessible acyl hydrazides by exploiting a novel aryne-based molecular rearrangement
  作者：André Shamsabadi、Vijay Chudasama

  DOI：10.1039/c8cc06556j

  日期：——

  A facile procedure for the conversion of readily accessible acyl hydrazides into 1H and 2H-indazoles via a novel aryne-based molecular rearrangement pathway.

  一种简便的将易得的酰基肼转化为1H和2H-吲唑的程序，通过一种基于新颖芳炔的分子重排途径。