8-chloro-3-phenylquinoline | 1373117-70-4

• 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: 8-chloro-3-phenylquinoline
• 英文别名: 8-Chloro-3-phenylquinoline
• CAS: 1373117-70-4
• 化学式: C₁₅H₁₀ClN
• 分子量: 239.704
• InChiKey: KRUIFBBIQXFTGI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  3.0
• 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：

  氧化苯乙烯 、 邻氯苯胺 在 iron(III) chloride 作用下， 以 1,4-二氧六环 为溶剂， 反应 12.0h， 以50%的产率得到8-chloro-3-phenylquinoline
  参考文献：
  名称：

  Iron-Promoted Tandem Reaction of Anilines with Styrene Oxides via C–C Cleavage for the Synthesis of Quinolines

  摘要：

  A novel iron-promoted tandem reaction of anilines with styrene oxides via C-C cleavage and C-H activation has been developed. The reaction utilizes an inexpensive FeCl3 as promoter and is suitable for forming a variety of 3-aryiquinolines from the simple and readily available starting materials.

  DOI：

  10.1021/ol300391t

文献信息

• [3+1+1+1] Annulation to the Pyridine Structure in Quinoline Molecules Based on DMSO as a Nonadjacent Dual-Methine Synthon: Simple Synthesis of 3-Arylquinolines from Arylaldehydes, Arylamines, and DMSO
  作者：Tonglin Yang、Hui Li、Zhiwen Nie、Miao-dong Su、Wei-ping Luo、Qiang Liu、Can-Cheng Guo

  DOI：10.1021/acs.joc.1c02708

  日期：2022.3.4

  A [3+1+1+1] annulation of arylamines, arylaldehydes, and dimethyl sulfoxide (DMSO) to the pyridine structure in quinolines using DMSO as a nonadjacent dual-methine (═CH−) synthon is disclosed. In this annulation, arylamines provide two carbon atoms and one nitrogen atom, arylaldehydes furnish one carbon atom, and DMSO provides two nonadjacent methines (═CH−) to the pyridine ring in quinoline molecules

  公开了使用 DMSO 作为不相邻的双次甲基 (=CH-) 合成子，芳胺、芳醛和二甲基亚砜 (DMSO) 与吡啶结构的 [3+1+1+1] 环化反应。在这种环化过程中，芳胺提供两个碳原子和一个氮原子，芳醛提供一个碳原子，DMSO 提供两个不相邻的次甲基 (=CH-) 到喹啉分子中的吡啶环。这种环化为从容易获得的底物以有用的产率合成 3-芳基喹啉提供了一种简单的方法。在对照实验和文献的基础上，提出了一种似是而非的机制。
• Solvent-free and room temperature synthesis of 3-arylquinolines from different anilines and styrene oxide in the presence of Al₂O₃/MeSO₃H
  作者：Hashem Sharghi、Mahdi Aberi、Mohsen Khataminejad、Pezhman Shiri

  DOI：10.3762/bjoc.13.193

  日期：——

  A highly efficient, simple and environmentally friendly synthesis of 3-arylquinolines has been developed in the presence of Al2O3/MeSO3H via one-pot reaction of anilines and styrene oxide. This methodology provides very rapid access to 3-arylquinolines in good to excellent yields under solvent-free conditions at room temperature in air.

  通过苯胺和氧化苯乙烯的一锅反应，在Al2O3 / MeSO3H存在下开发了一种高效，简单且环保的3-芳基喹啉合成方法。在无溶剂条件下，室温下在空气中，该方法可以非常快速地获得3-芳基喹啉，收率非常好。
• Palladium-catalyzed desulfitative arylation of 3-haloquinolines with arylsulfinates
  作者：Julie Colomb、Thierry Billard

  DOI：10.1016/j.tetlet.2013.01.018

  日期：2013.3

  3-Haloquinolines can be functionalized via a palladium-catalyzed desulfitative coupling of arylsulfinates. This method tolerates substitution upon the aromatic ring and shows good selectivity toward variously substituted aromatic rings. (C) 2013 Elsevier Ltd. All rights reserved.
• Iron-Promoted Tandem Reaction of Anilines with Styrene Oxides via C–C Cleavage for the Synthesis of Quinolines
  作者：Yicheng Zhang、Min Wang、Pinhua Li、Lei Wang

  DOI：10.1021/ol300391t

  日期：2012.5.4

  A novel iron-promoted tandem reaction of anilines with styrene oxides via C-C cleavage and C-H activation has been developed. The reaction utilizes an inexpensive FeCl3 as promoter and is suitable for forming a variety of 3-aryiquinolines from the simple and readily available starting materials.