3-acetyl-4'-nitrobiphenyl

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-acetyl-4'-nitrobiphenyl
• 英文别名: 1-[3-(4-Nitrophenyl)phenyl]ethanone；1-[3-(4-nitrophenyl)phenyl]ethanone
• 化学式: C₁₄H₁₁NO₃
• 分子量: 241.246
• InChiKey: AJBNYXDWEWRXOF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  62.9
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-acetyl-4'-nitrobiphenyl 在 tris(2,2-bipyridine)ruthenium(II) hexafluorophosphate 、 3C₉₃H₇₂N₈O₄P₄^(4-)*6Co⁽²⁺⁾ 、 醌氢醌 、 维生素 C 作用下， 以 水 、 乙腈 为溶剂， 反应 12.0h， 以99%的产率得到3-acetyl-4'-aminobiphenyl
  参考文献：
  名称：

  A new cobalt triangular prism supramolecular flask: Encapsulation of a quinhydrone cofactor for hydrogenation of nitroarenes with high selectivity and efficiency

  摘要：

  A new M6L3 metal-organic triangular prism host Co-L-1 was synthesized that contains a sufficiently large cavity for encapsulation of a quinhydrone (QHQ) electron transporter to form charge-transfer complexes for accelerating electron delivery. Through the strong coordinating ability of the ONP chelator, a suitable redox potential was obtained for the combination of light-driven proton reduction with the selective hydrogenation of nitro groups. The experimental results showed that the regulation of redox potential is very beneficial for hydrogen production and that the introduction of QHQ accelerates electron transfer and increases the reaction rate. Control experiments based on an inhibitor and a mononuclear compound resembling the cobalt corner of the triangular prism suggest enzyme-like behaviour. This synthetic platform, in which the supramolecular systems exhibit high activity and stability, provides an alternative strategy to selectively hydrogenate nitroarenes using light as a clean energy source.

  DOI：

  10.1016/j.inoche.2019.107558
• 作为产物：
  描述：

  3-乙酰基苯硼酸 在 palladium on activated charcoal sodium carbonate 、 magnesium sulfate 作用下， 以 乙醇 、 二氯甲烷 、 水 为溶剂， 反应 4.0h， 生成 3-acetyl-4'-nitrobiphenyl
  参考文献：
  名称：

  Heterogeneous Pd/C-catalyzed ligand-free Suzuki–Miyaura coupling reaction using aryl boronic esters

  摘要：

  Heterogeneous Pd/C-catalyzed Suzuki-Miyaura cross-coupling reaction of aryl boronic esters with aryl bromides was successfully carried out in aqueous media at room temperature without the use of a ligand such as phosphine derivatives. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2007.08.017

文献信息

• Immobilized Pd on magnetic nanoparticles bearing proline as a highly efficient and retrievable Suzuki–Miyaura catalyst in aqueous media
  作者：E. Nehlig、B. Waggeh、N. Millot、Y. Lalatonne、L. Motte、E. Guénin

  DOI：10.1039/c4dt02899f

  日期：——

  Immobilized Pd on magnetic nanoparticles bearing proline as a highly efficient and retrievable Suzuki–Miyaura catalyst in aqueous media.

  在水介质中，携带脯氨酸的磁性纳米颗粒上固定的Pd是一种高效可回收的Suzuki-Miyaura催化剂。
• d-Glucosamine based-phosphine for Suzuki-Miyaura cross-coupling reactions in the supported aqueous phase catalysis system
  作者：Karolina Wójcik、Catherine Goux-Henry、Bruno Andrioletti、K. Michał Pietrusiewicz、Eric Framery

  DOI：10.1016/j.tetlet.2012.07.138

  日期：2012.10

  A D-glucosamine-based phosphine/Pd(OAc)(2) complex has been applied to the Suzuki-Miyaura coupling reaction of aryl bromides with arylboronic acids using the supported aqueous phase catalysis, SAPC, concept. The recyclability of the catalyst was investigated and revealed a very high activity during the 4 runs. (C) 2012 Elsevier Ltd. All rights reserved.
• Heterogeneous Pd/C-catalyzed ligand-free Suzuki–Miyaura coupling reaction using aryl boronic esters
  作者：Yoshiaki Kitamura、Ai Sakurai、Takahiro Udzu、Tomohiro Maegawa、Yasunari Monguchi、Hironao Sajiki

  DOI：10.1016/j.tet.2007.08.017

  日期：2007.10

  Heterogeneous Pd/C-catalyzed Suzuki-Miyaura cross-coupling reaction of aryl boronic esters with aryl bromides was successfully carried out in aqueous media at room temperature without the use of a ligand such as phosphine derivatives. (C) 2007 Elsevier Ltd. All rights reserved.
• A new cobalt triangular prism supramolecular flask: Encapsulation of a quinhydrone cofactor for hydrogenation of nitroarenes with high selectivity and efficiency
  作者：Sijia Zheng、Liang Zhao、Jianwei Wei、Cheng He、Guangzhou Liu、Chunying Duan

  DOI：10.1016/j.inoche.2019.107558

  日期：2019.11

  A new M6L3 metal-organic triangular prism host Co-L-1 was synthesized that contains a sufficiently large cavity for encapsulation of a quinhydrone (QHQ) electron transporter to form charge-transfer complexes for accelerating electron delivery. Through the strong coordinating ability of the ONP chelator, a suitable redox potential was obtained for the combination of light-driven proton reduction with the selective hydrogenation of nitro groups. The experimental results showed that the regulation of redox potential is very beneficial for hydrogen production and that the introduction of QHQ accelerates electron transfer and increases the reaction rate. Control experiments based on an inhibitor and a mononuclear compound resembling the cobalt corner of the triangular prism suggest enzyme-like behaviour. This synthetic platform, in which the supramolecular systems exhibit high activity and stability, provides an alternative strategy to selectively hydrogenate nitroarenes using light as a clean energy source.