3-ethoxy-4’-nitrobiphenyl | 1362419-09-7

• 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-ethoxy-4’-nitrobiphenyl
• 英文别名: 3-ethoxy-4'-nitrobiphenyl；1-Ethoxy-3-(4-nitrophenyl)benzene
• CAS: 1362419-09-7
• 化学式: C₁₄H₁₃NO₃
• 分子量: 243.262
• InChiKey: IFFIGNAXIXLQBV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  55
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  4-硝基碘苯 、 3-乙氧基苯硼酸 在 C₇₀H₄₀Cl₂F₆₈N₂O₆Pd₂ 、 四丁基溴化铵 、 potassium carbonate 作用下， 以 水 为溶剂， 反应 0.03h， 以94%的产率得到3-ethoxy-4’-nitrobiphenyl
  参考文献：
  名称：

  Fluorous Oxime Palladacycle: A Precatalyst for Carbon–Carbon Coupling Reactions in Aqueous and Organic Medium

  摘要：

  To facilitate precatalyst recovery and reuse, we have developed a fluorous, oxime-based palladacycle 1 and demonstrated that it is a very efficient and versatile precatalyst for a wide range of carbon carbon bond formation reactions (Suzuki-Miyaura, Sonogashira, Stille, Heck, Glaser-type, and Kumada) in either aqueous or organic medium under microwave irradiation. Palladacycle 1 could be recovered through F-SPE in various coupling reactions with recovery ranging from 84 to 95% for the first cycle. Inductively coupled plasma optical emission spectrometry (ICP-OES) analyses of the Pd content in the crude product from each class of transformation indicated extremely low levels of leaching and the palladacycle could be reused four to five times without significant loss of activity.

  DOI：

  10.1021/jo202482h

文献信息

• Micellar catalysis of the Suzuki Miyaura reaction using biogenic Pd nanoparticles from <i>Desulfovibrio alaskensis</i>
  作者：Yuta Era、Jonathan A. Dennis、Stephen Wallace、Louise E. Horsfall

  DOI：10.1039/d1gc02392f

  日期：——

  biogenic palladium nanoparticles generated by the sulfate-reducing bacterium Desulfovibrio alaskensis G20 catalyse the ligand-free Suzuki Miyaura reaction of abiotic substrates. The reaction is highly efficient (>99% yield, 0.5 mol% Pd), occurs under mild conditions (37 °C, aqueous media) and can be accelerated within biocompatible micelles at the cell membrane to yield products containing challenging

  微生物在接触有毒金属离子后会产生金属纳米颗粒 (MNP)。然而，尽管这些生物过程有可能用于可持续回收包括钯在内的关键金属，但生物合成 MNP 的催化活性仍未得到充分探索。在这里，我们报告了由硫酸盐还原菌Desulfovibrio alaskensis产生的生物钯纳米颗粒G20 催化非生物底物的无配体 Suzuki Miyaura 反应。该反应非常高效（产率>99%，Pd 含量为 0.5 mol%），在温和条件下（37 °C，水性介质）发生，并且可以在细胞膜上的生物相容性胶束内加速，产生含有挑战性联芳基键的产物。这项工作强调了厌氧菌的天然代谢过程如何与绿色化学技术相结合，产生高效的催化反应，用于可持续的有机合成。
• Fluorous Oxime Palladacycle: A Precatalyst for Carbon–Carbon Coupling Reactions in Aqueous and Organic Medium
  作者：Woen Susanto、Chi-Yuan Chu、Wei Jie Ang、Tzyy-Chao Chou、Lee-Chiang Lo、Yulin Lam

  DOI：10.1021/jo202482h

  日期：2012.3.16

  To facilitate precatalyst recovery and reuse, we have developed a fluorous, oxime-based palladacycle 1 and demonstrated that it is a very efficient and versatile precatalyst for a wide range of carbon carbon bond formation reactions (Suzuki-Miyaura, Sonogashira, Stille, Heck, Glaser-type, and Kumada) in either aqueous or organic medium under microwave irradiation. Palladacycle 1 could be recovered through F-SPE in various coupling reactions with recovery ranging from 84 to 95% for the first cycle. Inductively coupled plasma optical emission spectrometry (ICP-OES) analyses of the Pd content in the crude product from each class of transformation indicated extremely low levels of leaching and the palladacycle could be reused four to five times without significant loss of activity.