8-(4-(trifluoromethyl)phenyl)quinoline | 1275591-20-2

• 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-(4-(trifluoromethyl)phenyl)quinoline
• 英文别名: 8-[4-(Trifluoromethyl)phenyl]quinoline；8-[4-(trifluoromethyl)phenyl]quinoline
• CAS: 1275591-20-2
• 化学式: C₁₆H₁₀F₃N
• 分子量: 273.257
• InChiKey: NDKOFKSWMNSNSJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  20
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  12.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  8-(4-(trifluoromethyl)phenyl)quinoline 、 联硼酸频那醇酯 在 (1,5-cyclooctadiene)(methoxy)iridium(I) dimer 、 3-(5-methylpyridin-2-yl)benzonitrile 作用下， 以 四氢呋喃 为溶剂， 反应 12.0h， 以90%的产率得到8-(2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-4-(trifluoromethyl)phenyl)quinoline
  参考文献：
  名称：

  Iridium-Catalyzed Site-Selective Borylation of 8-Arylquinolines

  摘要：

  我们报告了一种方便的方法，用于高度位点选择性地对8-芳基喹啉进行硼化反应。在[Ir(OMe)(cod)]2和2-苯基吡啶衍生的配体存在下，使用双(二甲基苯基)二硼烷作为硼化试剂，反应顺利进行。这些反应在许多官能团的高选择性下发生，提供了一系列硼化的8-芳基喹啉，产率从良好到优异，选择性也非常好。这种方法形成的硼化化合物可以通过已知的转化反应转化为各种重要的合成子。

  DOI：

  10.1055/a-1506-3884
• 作为产物：
  描述：

  喹啉 、 对溴三氟甲苯 在 dirhodium tetraacetate 、 1,3-双(2,4,6-三甲基苯基)氯化咪唑 、 sodium t-butanolate 作用下， 以 甲苯 为溶剂， 反应 24.0h， 以87%的产率得到8-(4-(trifluoromethyl)phenyl)quinoline
  参考文献：
  名称：

  Rh(NHC)-Catalyzed Direct and Selective Arylation of Quinolines at the 8-Position

  摘要：

  A new catalytic protocol for the regioselective direct arylation of quinoline derivatives at the 8-position has been developed. The reaction is catalyzed by a Rh(NHC) system, and the choice of the NHC ligand was most important for achieving high reactivity and selectivity.

  DOI：

  10.1021/ja111670s

文献信息

• Pincer-Nickel-Catalyzed Cross-Coupling of Aryl Sulfamates with Arylzinc Chlorides
  作者：Jian-Long Tao、Zhong-Xia Wang

  DOI：10.1002/ejoc.201500987

  日期：2015.9

  The nickel N,N,N-pincer complex 2 was demonstrated to effectively catalyze the cross-coupling of aryl sulfamates with arylzinc chlorides under mild conditions. The reaction is suitable for a wide range of substrates, and tolerates various functional groups.

  镍 N,N,N-钳形配合物 2 被证明可以在温和条件下有效催化芳基氨基磺酸酯与芳基氯化锌的交叉偶联。该反应适用于广泛的底物，并耐受各种官能团。
• Catalytic asymmetric hydrogenation of quinoline carbocycles: unusual chemoselectivity in the hydrogenation of quinolines
  作者：Ryoichi Kuwano、Ryuhei Ikeda、Kazuki Hirasada

  DOI：10.1039/c5cc01971k

  日期：——

  A chiral PhTRAP–ruthenium catalyst selectively hydrogenates the quinoline carbocycles to afford 5,6,7,8-tetrahydroquinolines with up to 91 : 9 er.

  一个手性PhTRAP-钌催化剂选择性地加氢喹啉环，生成了5,6,7,8-四氢喹啉，其对映选择性高达91:9。
• Ru-Catalyzed Deoxygenative Regioselective C8–H Arylation of Quinoline <i>N</i>-Oxides
  作者：Jinwoo Kim、Suhyeon Kim、Dongwook Kim、Sukbok Chang

  DOI：10.1021/acs.joc.9b01548

  日期：2019.10.18

  Regioselective C-H functionalization on quinolines is of high interest to lead to value-added products. Herein, we describe the development of Ru-catalyzed deoxygenative regioselective C8 arylation of quinoline N-oxides with arylboronic esters. Mechanistic studies revealed that it proceeds in a tandem process of arylation and then deoxygenation, wherein both steps were found to be catalytic with the

  在喹啉上的区域选择性CH官能化引起了增值产品的高度关注。本文中，我们描述了Ru催化喹啉N-氧化物与芳基硼酸酯的脱氧区域选择性C8芳基化的发展。机理研究表明，它以芳基化然后脱氧的串联过程进行，其中发现两个步骤均与钌物种催化。
• Rh(NHC)-Catalyzed Direct and Selective Arylation of Quinolines at the 8-Position
  作者：Jaesung Kwak、Min Kim、Sukbok Chang

  DOI：10.1021/ja111670s

  日期：2011.3.23

  A new catalytic protocol for the regioselective direct arylation of quinoline derivatives at the 8-position has been developed. The reaction is catalyzed by a Rh(NHC) system, and the choice of the NHC ligand was most important for achieving high reactivity and selectivity.
• Iridium-Catalyzed Site-Selective Borylation of 8-Arylquinolines
  作者：Buddhadeb Chattopadhyay、Mirja Md Mahamudul Hassan、Md Emdadul Hoque、Sayan Dey、Saikat Guria、Brindaban Roy

  DOI：10.1055/a-1506-3884

  日期：2021.9

  We report a convenient method for the highly site-selective borylation of 8-arylquinoline. The reaction proceeds smoothly in the presence of a catalytic amount of [Ir(OMe)(cod)]2 and 2-phenylpyridine derived ligand using bis(pinacolato)diborane as the borylating agent. The reactions occur with high selectivity with many functional groups, providing a series of borylated 8-aryl quinolines with good to excellent yield and excellent selectivity. The borylated compounds formed in this method can be transformed into various important synthons by using known transformations.

  我们报告了一种方便的方法，用于高度位点选择性地对8-芳基喹啉进行硼化反应。在[Ir(OMe)(cod)]2和2-苯基吡啶衍生的配体存在下，使用双(二甲基苯基)二硼烷作为硼化试剂，反应顺利进行。这些反应在许多官能团的高选择性下发生，提供了一系列硼化的8-芳基喹啉，产率从良好到优异，选择性也非常好。这种方法形成的硼化化合物可以通过已知的转化反应转化为各种重要的合成子。