5-phenylbenzo[f]quinoline | 23827-05-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 5-phenylbenzo[f]quinoline
• 英文别名: 10-Phenyl-1-aza-phenanthren；5-Phenylbenzo[f]quinoline
• CAS: 23827-05-6
• 化学式: C₁₉H₁₃N
• 分子量: 255.319
• InChiKey: DOTBPUJFBFPPGV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  20
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  12.9
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  5.6-苯并喹啉 、 溴苯 在 dirhodium tetraacetate 、 1,3-双(2,4,6-三甲基苯基)氯化咪唑 、 sodium t-butanolate 作用下， 以 甲苯 为溶剂， 反应 24.0h， 以94%的产率得到5-phenylbenzo[f]quinoline
  参考文献：
  名称：

  Rh(NHC)-Catalyzed Direct and Selective Arylation of Quinolines at the 8-Position

  摘要：

  A new catalytic protocol for the regioselective direct arylation of quinoline derivatives at the 8-position has been developed. The reaction is catalyzed by a Rh(NHC) system, and the choice of the NHC ligand was most important for achieving high reactivity and selectivity.

  DOI：

  10.1021/ja111670s

文献信息

• Extended Study of Visible-Light-Induced Photocatalytic [4 + 2] Benzannulation: Synthesis of Polycyclic (Hetero)Aromatics
  作者：Tanmay Chatterjee、Da Seul Lee、Eun Jin Cho

  DOI：10.1021/acs.joc.7b00413

  日期：2017.4.21

  extended study of [4 + 2] benzannulation reactions of 2-(hetero)aryl-substituted anilines with alkynes by visible light photocatalysis. The method requires the use of tBuONO as a diazotizing agent and 0.3 mol % of fac-Ir(ppy)3 as a photocatalyst at room temperature. The reaction proceeded in a chemo- and regioselective manner with high functional group tolerance under mild conditions allowing the preparation

  本文中，我们报道了2-（杂）芳基取代的苯胺与炔烃的[4 + 2]苯并环反应通过可见光催化的扩展研究。该方法需要在室温下使用t BuONO作为重氮化剂，并使用0.3 mol％的fac -Ir（ppy）3作为光催化剂。反应在温和条件下以化学和区域选择性方式进行，具有较高的官能团耐受性，从而可以以中等至高收率制备各种多环（杂）芳族化合物，包括菲。该方法适用于9-苯基菲的克规模合成。
• Electrochemically driven [4+2] benzannulation: synthesis of polycyclic (hetero)aromatic compounds
  作者：Yunlong Liu、Pengcheng Zhou、Yingli Xu、Zhiqi Yang、Dong Wang

  DOI：10.1039/d2cc06552e

  日期：——

  A green and economical electrochemical protocol has been developed to synthesize polycyclic (hetero)aromatic compounds by the [4+2] benzannulation of biaryldiazonium salts with alkynes. This protocol features a broad substrate scope. Instead of requiring diazonium reagents, these reactions can begin from anilines and can be carried out in one pot. Moreover, the readily accessible scale-up synthesis

  开发了一种绿色且经济的电化学方案，通过联芳基重氮盐与炔烃的 [4+2] 苯并环化反应合成多环（杂）芳族化合物。该协议具有广泛的底物范围。这些反应不需要重氮试剂，而是可以从苯胺开始，并且可以在一锅中进行。此外，通过使用电化学流动池实现的易于访问的放大合成证明了该协议的合成潜力。
• Rh(NHC)-Catalyzed Direct and Selective Arylation of Quinolines at the 8-Position
  作者：Jaesung Kwak、Min Kim、Sukbok Chang

  DOI：10.1021/ja111670s

  日期：2011.3.23

  A new catalytic protocol for the regioselective direct arylation of quinoline derivatives at the 8-position has been developed. The reaction is catalyzed by a Rh(NHC) system, and the choice of the NHC ligand was most important for achieving high reactivity and selectivity.