2-(2-nitrophenyl)-1-(1,1'-biphenyl)phenylethanone | 1443152-92-8

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二芳基庚烷
• 英文名称: 2-(2-nitrophenyl)-1-(1,1'-biphenyl)phenylethanone
• 英文别名: 2-(2-Nitrophenyl)-1-(4-phenylphenyl)ethanone
• CAS: 1443152-92-8
• 化学式: C₂₀H₁₅NO₃
• 分子量: 317.344
• InChiKey: FBCBYBGOJGVFJT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.05
• 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：

  2-(2-nitrophenyl)-1-(1,1'-biphenyl)phenylethanone 在 二氢吡啶 、 palladium 10% on activated carbon 作用下， 以 溶剂黄146 为溶剂， 反应 10.0h， 以93%的产率得到2-联苯-4-基-1H-吲哚
  参考文献：
  名称：

  钯催化Hantzsch酯合成2-取代吲哚

  摘要：

  An efficient reductive cyclization of o-nitrobenzyl ketone compounds was achieved by using a Hantzsch 1,4-dihydropyridine ester as a biomimetic reducing agent in the presence of catalytic palladium on carbon. 2-Substituted indoles were obtained in good yields. Investigation of the mechanism suggests that palladium hydride promotes the reduction of nitro group, and acetic acid was beneficial for the loss of water to produce the intended product. This reaction system can not only broaden the use of Hantzsch 1,4-dihydropyridine ester, but it also provides a novel approach for preparing indole compounds.

  DOI：

  10.3987/com-18-14022
• 作为产物：
  描述：

  在 pyridinium chlorochromate 作用下， 以 二氯甲烷 为溶剂， 生成 2-(2-nitrophenyl)-1-(1,1'-biphenyl)phenylethanone
  参考文献：
  名称：

  钯催化Hantzsch酯合成2-取代吲哚

  摘要：

  An efficient reductive cyclization of o-nitrobenzyl ketone compounds was achieved by using a Hantzsch 1,4-dihydropyridine ester as a biomimetic reducing agent in the presence of catalytic palladium on carbon. 2-Substituted indoles were obtained in good yields. Investigation of the mechanism suggests that palladium hydride promotes the reduction of nitro group, and acetic acid was beneficial for the loss of water to produce the intended product. This reaction system can not only broaden the use of Hantzsch 1,4-dihydropyridine ester, but it also provides a novel approach for preparing indole compounds.

  DOI：

  10.3987/com-18-14022

文献信息

• Palladium and copper catalyzed one-pot Sonogashira reaction of 2-nitroiodobenzenes with aryl acetylenes and subsequent regioselective hydration in water: synthesis of 2-(2-nitrophenyl)-1-aryl ethanones
  作者：Sabir Ahammed、Raju Dey、Brindaban C. Ranu

  DOI：10.1016/j.tetlet.2013.05.021

  日期：2013.7

  An attempted Sonogashira reaction of 2-nitroiodobenzene and phenyl acetylene catalyzed by Pd(PPh3)(4)/Cu in water in the presence of pyrrolidine proceeds with simultaneous regioselective hydration of the Sonogashira alkyne leading to the corresponding aryl ketone. A series of functionalized 2-(2-nitrophenyl)-1-aryl ethanones are obtained in high yields by this procedure. (C) 2013 Elsevier Ltd. All rights reserved.