3-Nitro-benzophenon-phenylhydrazon | 22918-32-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 3-Nitro-benzophenon-phenylhydrazon
• 英文别名: p-Nitro-benzophenon-phenylhydrazon；4-nitro-benzophenone-phenylhydrazone；4-Nitro-benzophenon-phenylhydrazon；N-[[(4-nitrophenyl)-phenylmethylidene]amino]aniline
• CAS: 22918-32-7
• 化学式: C₁₉H₁₅N₃O₂
• 分子量: 317.347
• InChiKey: ZDWLOSBQMVDLFZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.46
• 重原子数：
  24.0
• 可旋转键数：
  5.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  67.53
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  3-Nitro-benzophenon-phenylhydrazon 在 Oxone 、 碘苯 、 三氟乙酸 作用下， 反应 0.5h， 以79%的产率得到3-(4-nitro-phenyl)-1-phenyl-1H-indazole
  参考文献：
  名称：

  在温和、无过渡金属条件下通过碘苯催化的 CH 胺化轻松获得 1H-吲唑

  摘要：

  N-芳基取代的1H-吲唑及其衍生物的无过渡金属和无卤素合成是在碘苯催化的腙分子内C-H胺化反应的基础上在温和条件下完成的。由酮和肼衍生的腙与催化量的碘苯在 Oxone 作为氧化剂的三氟乙酸中发生反应，以中等至良好的产率得到 1H-吲唑。在对照实验的基础上描述了一个合理的反应机理。

  DOI：

  10.1002/ejoc.201402488
• 作为产物：
  描述：

  4-硝基二苯甲酮 、 苯肼 在 溶剂黄146 作用下， 以 乙醇 为溶剂， 反应 5.0h， 生成 3-Nitro-benzophenon-phenylhydrazon
  参考文献：
  名称：

  An efficient transition-metal-free synthesis of 1H-indazoles from arylhydrazones with montmorillonite K-10 under O2 atmosphere

  摘要：

  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.

  DOI：

  10.1016/j.tetlet.2015.01.183

文献信息

• Facile Access to 1<i>H</i>-Indazoles through Iodobenzene-Catalyzed C-H Amination under Mild, Transition-Metal-Free Conditions
  作者：Mitsuhiro Kashiwa、Motohiro Sonoda、Shinji Tanimori

  DOI：10.1002/ejoc.201402488

  日期：2014.8

  1H-indazole and derivatives was accomplished on the basis of the iodobenzene-catalyzed intramolecular C–H amination of hydrazones under mild conditions. Reactions of hydrazones derived from ketones and hydrazines with a catalytic amount of iodobenzene in the presence of Oxone as an oxidant in trifluoroacetic acid took place to afford 1H-indazoles in moderate to good yields. A plausible reaction mechanism

  N-芳基取代的1H-吲唑及其衍生物的无过渡金属和无卤素合成是在碘苯催化的腙分子内C-H胺化反应的基础上在温和条件下完成的。由酮和肼衍生的腙与催化量的碘苯在 Oxone 作为氧化剂的三氟乙酸中发生反应，以中等至良好的产率得到 1H-吲唑。在对照实验的基础上描述了一个合理的反应机理。
• Visible-light-induced [3+3] cycloaddition reaction of phenol and hydrazone to access 1,3,4-oxadiazines scaffolds
  作者：Xuebin Qiao、Yu Han、Sijun Huang、Yanyang Sun、Chunyu Wang、Zhi Wang、Fengxi Li、Lei Wang

  DOI：10.1016/j.mcat.2024.114156

  日期：2024.5

  In this study, we present a novel photocatalytic-mediated approach for facilitating the [3 + 3] oxidative cycloaddition reaction of phenols and hydrazones. By utilizing visible light irradiation, this reaction is executed in an efficient, mild, and eco-friendly manner, without requiring any oxidants or additives. The versatility of this method is evidenced by the successful synthesis of 1,3,4-oxadiazine

  在这项研究中，我们提出了一种新的光催化介导的方法，用于促进酚和腙的[3 + 3]氧化环加成反应。通过利用可见光照射，该反应以高效、温和且环保的方式进行，不需要任何氧化剂或添加剂。该方法的多功能性通过以令人满意的收率成功合成具有各种取代基的1,3,4-恶二嗪衍生物得到证明。此外，通过受控实验和密度泛函理论计算（DFT）阐明了反应的可能机制。
• Synthesis of 1<i>H</i>-Indazoles and 1<i>H</i>-Pyrazoles via FeBr₃/O₂ Mediated Intramolecular C–H Amination
  作者：Tianshui Zhang、Weiliang Bao

  DOI：10.1021/jo3026862

  日期：2013.2.1

  A new synthesis of substituted 1H-indazoles and 1H-pyrazoles from arylhydrazones via FeBr3/O-2 mediated C-H activation/C-N bond formation reactions is reported. The corresponding 1,3-diaryl-substituted indazoles and trisubstituted pyrazoles were obtained in moderate to excellent yields under mild conditions.
• Hemin-Catalyzed Oxidative Phenol-Hydrazone [3+3] Cycloaddition Enables Rapid Construction of 1,3,4-Oxadiazines
  作者：Honghua Zuo、Jingyang Qin、Wentao Zhang、Muhammad Adnan Bashir、Qile Yu、Weining Zhao、Guojiao Wu、Fangrui Zhong

  DOI：10.1021/acs.orglett.0c02442

  日期：2020.9.4

  Herein, we present a hemin-catalyzed oxidative phenol-hydrazone [3+3] cycloaddition that accommodates a broad spectrum of N-arylhydrazones, a class of less exploited 1,3-dipoles due to their significant Lewis basicity and weak tendency to undergo 1,2-prototropy to form azomethine imines. It renders expedient assembly of diversely functionalized 1,3,4-oxadiazines with excellent atom and step economy. Preliminary mechanistic studies point to the involvement of a one-electron oxidation pathway, which likely differs from the base-promoted aerobic oxidative scenario.
• 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.