3,6-dimethyl-2,4-diphenylquinoline | 109704-24-7

• 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: 3,6-dimethyl-2,4-diphenylquinoline
• 英文别名: Quinoline, 3,6-dimethyl-2,4-diphenyl-
• CAS: 109704-24-7
• 化学式: C₂₃H₁₉N
• 分子量: 309.411
• InChiKey: FKVNQXGKQCEAEN-UHFFFAOYSA-N

物化性质

• 熔点：
  138-140 °C
• 沸点：
  442.9±24.0 °C(Predicted)
• 密度：
  1.105±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.2
• 重原子数：
  24
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.09
• 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：

  在 potassium tert-butylate 、 二甲基亚砜 作用下， 反应 4.0h， 以74%的产率得到3,6-dimethyl-2,4-diphenylquinoline
  参考文献：
  名称：

  Synthesis of Polysubstituted Quinolines via Transition-Metal-Free Oxidative Cycloisomerization of o-Cinnamylanilines

  摘要：

  An efficient synthesis of 2-aryl 4-substituted quinolines from stable and readily available o-cinnamylanilines, prepared from anilines and cinnamylalcohols, has been developed. The reaction occurred via a regioselective 6-endo-trig intramolecular oxidative cyclization using (KOBu)-Bu-t as a mediator and DMSO as an oxidant at rt. The reaction showed a broad substrate scope with good to excellent yields.

  DOI：

  10.1021/acs.orglett.5b00419

文献信息

• Photochemistry of 3-amino-2-alkenimines: Synthesis of substituted quinolines
  作者：Pedro J. Campos、Cheng-Quan Tan、José M. González、Miguel A. Rodríguez

  DOI：10.1016/s0040-4039(00)73985-2

  日期：1993.8

  The 3-amino-2-alkinimines 1 are photochemically reactives. Their irradiation in solution (tetrahydrofuran, methanol, diethyl ether, toluene) produces substituted quinolines 2 in good to acceptable yields. A six electon electrocyclic process is proposed.

  3-氨基-2-炔亚胺1是光化学反应性。它们在溶液（四氢呋喃，甲醇，乙醚，甲苯）中的辐照可产生令人满意的产率的取代喹啉2。提出了六种电子循环方法。
• Lewis Acid-Catalyzed Cyclization of 3-Amino-2-alkenimines. Synthesis of Quinolines
  作者：José Barluenga、Humildad Cuervo、Santos Fustero、Vicente Gotor

  DOI：10.1055/s-1987-27858

  日期：——

  3-Amino-2-alkenimines react with aluminium chloride to afford quinolines in a regioselective manner.

  3-Amino-2-alkenimines 与氯化铝发生反应，以区域选择性方式生成喹啉类化合物。
• BARLUENGA J.; CUERVO H.; FUSTERO S.; GOTOR V., SYNTHESIS,(1987) N 1, 82-84
  作者：BARLUENGA J.、 CUERVO H.、 FUSTERO S.、 GOTOR V.

  DOI：——

  日期：——
• Synthesis of Polysubstituted Quinolines via Transition-Metal-Free Oxidative Cycloisomerization of <i>o</i>-Cinnamylanilines
  作者：Mohammad Rehan、Gurupada Hazra、Prasanta Ghorai

  DOI：10.1021/acs.orglett.5b00419

  日期：2015.4.3

  An efficient synthesis of 2-aryl 4-substituted quinolines from stable and readily available o-cinnamylanilines, prepared from anilines and cinnamylalcohols, has been developed. The reaction occurred via a regioselective 6-endo-trig intramolecular oxidative cyclization using (KOBu)-Bu-t as a mediator and DMSO as an oxidant at rt. The reaction showed a broad substrate scope with good to excellent yields.