3-(4-nitrophenyl)-1-phenylbenzo[f]quinoline | 53855-23-5

• 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: 3-(4-nitrophenyl)-1-phenylbenzo[f]quinoline
• 英文别名: 3-(4-Nitro-phenyl)-1-phenyl-benzo[f]chinolin
• CAS: 53855-23-5
• 化学式: C₂₅H₁₆N₂O₂
• 分子量: 376.414
• InChiKey: VOUSPLFCGAPYIE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.6
• 重原子数：
  29
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  58.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-(4-nitrophenyl)-1-phenylbenzo[f]quinoline 、 氯化亚锡 、 盐酸 以50%的产率得到
  参考文献：
  名称：

  KOZLOV N. S.; KOROBCHENKO L. V.; TSVIRKO M. P., XIMIYA GETEROTSIKL. SOEDIN. , 1976, HO 1, 116-120

  摘要：

  DOI：
• 作为产物：
  描述：

  N-萘-2-基-1-(4-硝基苯基)甲亚胺 、 苯乙酮 在 2-萘胺盐酸盐 作用下， 生成 3-(4-nitrophenyl)-1-phenylbenzo[f]quinoline
  参考文献：
  名称：

  Koslow; Schur, Doklady Akademii Nauk SSSR, 1958, vol. 123, p. 102,104

  摘要：

  DOI：

文献信息

• An efficient synthesis of 1,3-diarylbenzo[<i>f</i>]quinolines from 2-halogenated acetophenone, aromatic aldehyde, and naphthalen-2-amine catalyzed by iodine
  作者：Xiang-Shan Wang、Qing Li、Jie Zhou、Shu-Jiang Tu

  DOI：10.1002/jhet.211

  日期：2009.11

  The three‐component reaction of aromatic aldehyde, naphthalen‐2‐amine and 2‐halogenated acetophenone in THF catalyzed by 5 mol % iodine at reflux unexpectedly gave 1,3‐diarylbenzo[f]quinolines, with halogen losing in the formation of the products. The formation of unexpected 1,3‐diarylbenzo[f]quinolines was tentatively explained by Cram's rule to one of the steps in the mechanism. J. Heterocyclic Chem

  芳香醛，萘-2-胺和2-卤代苯乙酮在THF中由5 mol％碘在回流条件下进行三组分反应，出乎意料地产生了1,3-二芳基苯并[ f ]喹啉，在形成产物时卤素损失。克莱姆法则初步解释了意外的1，3-二芳基苯并[ f ]喹啉的形成是该机理的其中一个步骤。J.杂环化​​学，（2009）。
• An Efficient and Highly Selective Method for the Synthesis of 3-Arylbenzo­quinoline Derivatives Catalyzed by Iodine via Three-Component Reactions
  作者：Xiang-Shan Wang、Qing Li、Jian-Rong Wu、Yu-Ling Li、Chang-Sheng Yao、Shu-Jiang Tu

  DOI：10.1055/s-2008-1067087

  日期：——

  A mild, efficient and highly selective method for the synthesis of benzo[ F]quinoline derivatives via three-component reactions of arylaldehydes, naphthalen-2-amine and ketones or β-keto esters using iodine as catalyst is described. It should be noted that only one product was obtained, with high selectivity, when ketones or β-keto esters with two different α-hydrogen atoms were chosen as reactants

  介绍了一种以碘为催化剂，通过芳醛、萘-2-胺和酮或β-酮酯的三组分反应合成苯并[F]喹啉衍生物的温和、高效和高选择性的方法。It should be noted that only one product was obtained, with high selectivity, when ketones or β-keto esters with two different α-hydrogen atoms were chosen as reactants.
• A highly selective method for the synthesis of 1,3-diarylbenzo[f]quinoline derivatives catalyzed by silver triflate
  作者：Xiang-Shan Wang、Jie Zhou、Mei-Mei Zhang、Wei Wang、Yu-Ling Li

  DOI：10.1007/s00706-011-0662-8

  日期：2012.6

  AbstractThe three-component reactions of aromatic aldehydes, naphthalen-2-amine, and phenylacetylene catalyzed by AgOTf in toluene selectively gave 1,3-diarylbenzo[f]quinolines in high yields. This procedure provides an efficient method for the synthesis of benzo[f]quinolines under mild reaction conditions and with high yields, high selectivity, and operational simplicity. Graphical abstract

  摘要AgOTf在甲苯中催化的芳香醛，萘-2-胺和苯乙炔的三组分反应选择性地高产率地生成1,3-二芳基苯并[ f ]喹啉。该方法提供了一种在温和的反应条件下以高收率，高选择性和操作简便性合成苯并[ f ]喹啉的有效方法。 图形概要