2,4-diphenylquinolin-6-ol | 5855-62-9

• 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: 2,4-diphenylquinolin-6-ol
• 英文别名: 6-hydroxy-2,4-diphenylquinoline
• CAS: 5855-62-9
• 化学式: C₂₁H₁₅NO
• 分子量: 297.356
• InChiKey: PIGMETUNMWJSOJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  23
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  33.1
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2,4-diphenylquinolin-6-ol 在 盐酸 、 sodium hydroxide 、 碳酸氢钠 、 sodium carbonate 、 magnesium sulfate 、 sodium nitrite 、 对氨基苯磺酸 作用下， 以 二甲基亚砜 、 甲苯 为溶剂， 反应 12.5h， 生成 8',10'-diphenyl-1,3,3-trimethylspiro(indoline-2,3'-[3H]pyrido[3,2-f][1,4]benzoxazine)
  参考文献：
  名称：

  Synthesis of photochromic spirooxazines from 1-amino-2-naphthols

  摘要：

  A synthetic access to photochromic spirooxazines is developed through the condensation of methylene-substituted azaheterocycles on 1-amino-2-naphthols in presence of an oxidizing agent. Compared to usual preparation of this kind of compounds (via 1-nitroso-2-naphthols), yields are generally good and approaches to Further spiroheterocyclic oxazines are possible. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4020(97)00640-6
• 作为产物：
  描述：

  2,4-diphenyl-6-methoxyquinoline 在 氢溴酸 、 溶剂黄146 作用下， 反应 24.0h， 以70%的产率得到2,4-diphenylquinolin-6-ol
  参考文献：
  名称：

  Synthesis of photochromic spirooxazines from 1-amino-2-naphthols

  摘要：

  A synthetic access to photochromic spirooxazines is developed through the condensation of methylene-substituted azaheterocycles on 1-amino-2-naphthols in presence of an oxidizing agent. Compared to usual preparation of this kind of compounds (via 1-nitroso-2-naphthols), yields are generally good and approaches to Further spiroheterocyclic oxazines are possible. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4020(97)00640-6

文献信息

• Efficient synthesis of 2,4-disubstituted quinolines: calix[n]arene-catalyzed Povarov-hydrogen-transfer reaction cascade
  作者：Juliana Baptista Simões、Ângelo de Fátima、Adão Aparecido Sabino、Luiz Claudio Almeida Barbosa、Sergio Antonio Fernandes

  DOI：10.1039/c4ra02036g

  日期：——

  A new calixarene-catalyzed cascade process, involving Povarov reaction and hydrogen transfer, for the synthesis of 2,4-disubstituted quinolines is described.

  描述了一种新的杯芳烃催化级联过程，涉及Povarov反应和氢转移，用于合成2,4-二取代喹啉。
• Leardini, Rino; Nanni, Daniele; Tundo, Antonio, Gazzetta Chimica Italiana, 1989, vol. 119, # 12, p. 637 - 642
  作者：Leardini, Rino、Nanni, Daniele、Tundo, Antonio、Zanardi, Giuseppe

  DOI：——

  日期：——
• Oxidative Povarov Reaction via sp³ C–H Oxidation of <i>N</i>-Benzylanilines Induced by Catalytic Radical Cation Salt: Synthesis of 2,4-Diarylquinoline Derivatives
  作者：Jing Liu、Fang Liu、Yingzu Zhu、Xingge Ma、Xiaodong Jia

  DOI：10.1021/acs.orglett.5b00244

  日期：2015.3.20

  Oxidative Povarov reaction of N-benzylanilines was realized under catalytic radical cation salt induced conditions. The mechanism studies revealed that a radical intermediate was involved in this catalytic oxidation. This method provides a new way to synthesize 2,4-diarylquinoline derivatives.
• Annulation reactions with iron(III) chloride: oxidation of imines
  作者：Rino Leardini、Daniele Nanni、Antonio Tundo、Giuseppe Zanardi、Fabrizio Ruggieri

  DOI：10.1021/jo00032a043

  日期：1992.3

  Aromatic imines react with phenylacetylene or styrene in an acetonitrile solution of iron(III) chloride to give quinolines 3 or their tetrahydro derivatives 11 together with variable amounts of products 4 arising from the reduction of the imines. The initial step appears to be a one-electron oxidation to generate iron(II) and an imine radical cation. When the reactions are carried out in the presence of stoichiometric amounts of tetrachloro-p-benzoquinone (chloranil), only quinolines 3 are obtained.
• Synthesis of quinolines involving electrophilic amination of arenes with sodium azide in polyphosphoric acid
  作者：A. S. Lyakhovnenko、M. M. Kugutov、A. V. Aksenov

  DOI：10.1007/s11172-011-0123-x

  日期：2011.4