2-甲基-6-(4-甲苯基)喹啉 | 1220450-27-0

• 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
• 中文名称: 2-甲基-6-(4-甲苯基)喹啉
• 英文名称: 2-methyl-6-(4-tolyl)quinoline
• 英文别名: 2-Methyl-6-(4-methylphenyl)quinoline；2-methyl-6-(4-methylphenyl)quinoline
• CAS: 1220450-27-0
• 化学式: C₁₇H₁₅N
• 分子量: 233.313
• InChiKey: KBKMBOVHTIQMMF-UHFFFAOYSA-N

物化性质

• 熔点：
  120-121 °C
• 沸点：
  376.3±11.0 °C(Predicted)
• 密度：
  1.087±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 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：

  6-氟-2-甲基喹啉 、 4-甲基苯硼酸新戊基二醇酯 在 bis(1,5-cyclooctadiene)nickel (0) 、 氟化锆 、 cesium fluoride 、 三环己基膦 作用下， 以 甲苯 为溶剂， 反应 12.0h， 以59%的产率得到2-甲基-6-(4-甲苯基)喹啉
  参考文献：
  名称：

  Nickel-Catalyzed Suzuki–Miyaura Reaction of Aryl Fluorides

  摘要：

  Two protocols for the nickel-catalyzed cross-coupling of aryl fluorides with aryl boronic esters have been developed. The first employs metal fluoride cocatalysts, such as ZrF4 and TiF4, which enable Suzuki-Miyaura reactions of aryl fluorides bearing electron-withdrawing (ketones, esters, and CF3), aryl and alkenyl groups as well as those comprising fused aromatic rings, such as fluoronaphthalenes and fluoroquinolines. The second protocol employs aryl fluorides bearing ortho-directing groups, which facilitate the difficult C-F bond activation process via cyclometalation. N-heterocycles, such as pyridines, quinolines, pyrazoles, and oxazolines, can successfully promote cross-coupling with an array of organoboronic esters. A study into the substituent effects with respect to both coupling components has provided fundamental insights into the mechanism of the nickel-catalyzed cross-coupling of aryl fluorides.

  DOI：

  10.1021/ja207759e

文献信息

• US8785487B2
  申请人：——

  公开号：US8785487B2

  公开（公告）日：2014-07-22
• US8933110B2
  申请人：——

  公开号：US8933110B2

  公开（公告）日：2015-01-13
• US9127021B2
  申请人：——

  公开号：US9127021B2

  公开（公告）日：2015-09-08
• [EN] INHIBITORS OF HCV NS5A<br/>[FR] INHIBITEURS DE NS5A DE VHC
  申请人：HOFFMANN LA ROCHE

  公开号：WO2013087743A1

  公开（公告）日：2013-06-20

  The present invention provides compounds, compositions and methods for the treatment of hepatitis C virus (HCV) infection. Also disclosed are pharmaceutical compositions containing such compounds and methods for using these compounds in the treatment of HCV infection.
• Nickel-Catalyzed Suzuki–Miyaura Reaction of Aryl Fluorides
  作者：Mamoru Tobisu、Tian Xu、Toshiaki Shimasaki、Naoto Chatani

  DOI：10.1021/ja207759e

  日期：2011.12.7

  Two protocols for the nickel-catalyzed cross-coupling of aryl fluorides with aryl boronic esters have been developed. The first employs metal fluoride cocatalysts, such as ZrF4 and TiF4, which enable Suzuki-Miyaura reactions of aryl fluorides bearing electron-withdrawing (ketones, esters, and CF3), aryl and alkenyl groups as well as those comprising fused aromatic rings, such as fluoronaphthalenes and fluoroquinolines. The second protocol employs aryl fluorides bearing ortho-directing groups, which facilitate the difficult C-F bond activation process via cyclometalation. N-heterocycles, such as pyridines, quinolines, pyrazoles, and oxazolines, can successfully promote cross-coupling with an array of organoboronic esters. A study into the substituent effects with respect to both coupling components has provided fundamental insights into the mechanism of the nickel-catalyzed cross-coupling of aryl fluorides.