4-trifluoromethyl-N-(quinolin-8-yl)-[1,1′-biphenyl]-2-carboxamide | 1436849-26-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 4-trifluoromethyl-N-(quinolin-8-yl)-[1,1′-biphenyl]-2-carboxamide
• 英文别名: N-(quinolin-8-yl)-4-(trifluoromethyl)-[1,1'-biphenyl]-2-carboxamide；N-(quinolin-8-yl)-4-(trifluoromethyl)[1,1'-biphenyl]-2-carboxamide；4-trifluoromethyl-N-(quinolin-8-yl)[1,1'-biphenyl]-2-carboxamide；2-phenyl-N-quinolin-8-yl-5-(trifluoromethyl)benzamide
• CAS: 1436849-26-1
• 化学式: C₂₃H₁₅F₃N₂O
• 分子量: 392.38
• InChiKey: HUGIYONRLNZHGZ-UHFFFAOYSA-N

物化性质

• 沸点：
  478.0±45.0 °C(Predicted)
• 密度：
  1.332±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  29
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.04
• 拓扑面积：
  42
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  N-(quinolin-8-yl)-3-(trifluoromethyl)benzamide 、 苯硼酸频哪醇酯 在 正丁基锂 、 iron(III)-acetylacetonate 、 ZnBr₂*C₆H₁₆N₂ 、 顺-1,2-双(二苯基膦)乙烯 、 1,2-二氯-2-甲基丙烷 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 0.67h， 以89%的产率得到4-trifluoromethyl-N-(quinolin-8-yl)-[1,1′-biphenyl]-2-carboxamide
  参考文献：
  名称：

  Iron-Catalyzed C(sp²)–H Bond Functionalization with Organoboron Compounds

  摘要：

  We report here that an iron-catalyzed directed CH functionalization reaction allows the coupling of a variety of aromatic, heteroaromatic, and olefinic substrates with alkenyl and aryl boron compounds under mild oxidative conditions. We rationalize these results by the involvement of an organoiron(III) reactive intermediate that is responsible for the CH bond-activation process. A zinc salt is crucial to promote the transfer of the organic group from the boron atom to the iron(III) atom.

  DOI：

  10.1021/ja5070763

文献信息

• Copper-Mediated<i>ortho</i>-Arylation of Benzamides with Arylboronic Acid
  作者：Qingwen Gui、Xiang Chen、Liang Hu、Dadian Wang、Jidan Liu、Ze Tan

  DOI：10.1002/adsc.201500884

  日期：2016.2.18

  The copper‐mediated direct ortho CH bond arylation of benzamide derivatives with arylboronic acids was achieved by employing an 8‐aminoquinoline moiety as the bidentate directing group. Various biaryls were synthesized in good yields with excellent regioselectivity. The reaction shows good functional group compatibility and proceeds in a highly selective manner at the ortho‐position of the benzamides

  铜-介导的直接邻Ç 与芳基硼酸的苯甲酰胺衍生物的H键的芳基化物通过采用8-氨基喹啉部分作为二齿导向基团来实现。各种联芳基以高收率合成，具有出色的区域选择性。该反应显示出良好的官能团相容性，并在苯甲酰胺的邻位上以高度选择性的方式进行。氘标记实验表明，邻Ç 苯甲酰胺的H键裂解参与了芳基化的速率决定步骤。
• Cobalt-promoted selective arylation of benzamides and acrylamides with arylboronic acids
  作者：Liang Hu、Qingwen Gui、Xiang Chen、Ze Tan、Gangguo Zhu

  DOI：10.1039/c6ob02224c

  日期：——

  A novel cobalt-promoted arylation of aryl C–H bonds with arylboronic acids has been realized by using 8-aminoquinoline as the directing group. A notable feature of this newly developed protocol is that acrylamides, which cannot be arylated using copper salts as the promoter, can also be efficiently arylated.

  一种新颖的钴促进的芳基C-H键与芳基硼酸的芳基化反应已经通过使用8-氨基喹啉作为导向基实现。这一新开发的方案的一个显著特点是，不能使用铜盐作为催化剂进行芳基化的丙烯酰胺也可以被高效地芳基化。
• Ruthenium-catalyzed direct arylation of C–H bonds in aromatic amides containing a bidentate directing group: significant electronic effects on arylation
  作者：Yoshinori Aihara、Naoto Chatani

  DOI：10.1039/c2sc21506c

  日期：——

  by a ruthenium-catalyzed reaction of aromatic amides having an 8-aminoquinoline moiety with aryl bromides. The reaction shows high functional group compatibility. The reaction proceeds in a highly selective manner at the less hindered C–H bonds of meta-substituted aromatic amides. Significant electronic effects are observed in Hammett plots. Electron-withdrawing groups on the aromatic amides facilitate

  的芳基化邻C-H键由具有与芳基溴化物的8-氨基喹啉基部分的芳族酰胺的钌催化反应来实现。该反应显示出高官能团相容性。该反应以较高选择性的方式在间位取代的芳族酰胺的C–H键受阻较小的位置进行。在Hammett图中观察到了明显的电子效应。芳族酰胺上的吸电子基团促进了反应。相反，芳基溴化物上的给电子基团和吸电子基团都加速了反应。
• Nickel(II)-Catalyzed Direct Arylation of C–H Bonds in Aromatic Amides Containing an 8-Aminoquinoline Moiety as a Directing Group
  作者：Ayana Yokota、Yoshinori Aihara、Naoto Chatani

  DOI：10.1021/jo501697n

  日期：2014.12.19

  Arylation via the cleavage of the ortho CH bonds by a nickel-catalyzed reaction of aromatic amides containing an 8-aminoquinoline moiety with aryl iodides is reported. The reaction shows a high functional group compatibility. The reaction proceeds in a highly selective manner at the less hindered CH bonds in the reaction of meta-substituted aromatic amides, irrespective of the electronic nature of the substituents. Electron-withdrawing groups on the aromatic amides facilitate the reaction. Various mechanistic experiments, such as deuterium labeling experiments, Hammett studies, competition experiments, and radical trap experiments, have been made for better understanding the reaction mechanism. It is found that the cleavage of CH bonds is reversible on the basis of the deuterium labeling experiments. Both Ni(II) and Ni(0) show a high catalytic activity, but the results of mechanistic experiments suggest that a Ni(0)/Ni(II) catalytic cycle is not involved.
• Iron-Catalyzed C(sp²)–H Bond Functionalization with Organoboron Compounds
  作者：Rui Shang、Laurean Ilies、Sobi Asako、Eiichi Nakamura

  DOI：10.1021/ja5070763

  日期：2014.10.15

  We report here that an iron-catalyzed directed CH functionalization reaction allows the coupling of a variety of aromatic, heteroaromatic, and olefinic substrates with alkenyl and aryl boron compounds under mild oxidative conditions. We rationalize these results by the involvement of an organoiron(III) reactive intermediate that is responsible for the CH bond-activation process. A zinc salt is crucial to promote the transfer of the organic group from the boron atom to the iron(III) atom.