10-(3,4-difluorophenyl)benzo[h]quinoline

• 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: 10-(3,4-difluorophenyl)benzo[h]quinoline
• 英文别名: 10-(3,4-Difluorophenyl)benzo[h]quinoline
• 化学式: C₁₉H₁₁F₂N
• 分子量: 291.3
• InChiKey: BFVPZARJLYHHOS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  22
• 可旋转键数：
  1
• 环数：
  4.0
• 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：
  3

反应信息

• 作为产物：
  描述：

  3,4-二氟苯甲酰氯 在 4-二甲氨基吡啶 、 chloro(1,5-cyclooctadiene)rhodium(I) dimer 、 三乙胺 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 15.0h， 生成 10-(3,4-difluorophenyl)benzo[h]quinoline
  参考文献：
  名称：

  铑通过双C–H / C–N键活化作用与酰胺催化的C–H键官能化

  摘要：

  据报道，在高化学选择性条件下，使用铑（I）催化剂通过酰胺N–C键的选择性活化，首次将酰胺作为偶联伙伴进行C–H键官能化。值得注意的是，该报告构成了铑对酰胺N–C（O）键的首次催化活化。我们预计，除了本文所述的工作以外，使用酰胺作为C–H活化的偶联伴侣将具有广泛的意义。

  DOI：

  10.1021/acs.orglett.6b00058

文献信息

• Rhodium-Catalyzed Cross-Coupling Reactions of Carboxylate and Organoboron Compounds via Chelation-Assisted C–C Bond Activation
  作者：Jingjing Wang、Bowen Liu、Haitao Zhao、Jianhui Wang

  DOI：10.1021/om300994j

  日期：2012.12.24

  A new rhodium-catalyzed decarbonylated coupling reaction of ethyl benzo[h]quinoline-10-carboxylate and organoboron compounds that occurs through chelation-assisted sp2 C–COOEt bond activation was described. In this system CuCl played a very important role, and a five-membered rhodacycle was also involved as a key intermediate. Various functionalities were compatible in the reaction, and the desired

  描述了一种新的铑催化的苯并[ h ]喹啉-10-羧酸乙酯与有机硼化合物的脱羰偶联反应，该反应通过螯合辅助的sp 2 C-COOEt键活化而发生。在该系统中，CuCl发挥了非常重要的作用，并且五元罗丹环也作为关键中间体参与其中。在反应中各种官能团是相容的，并且以良好至优异的产率获得了所需的产物。还已经使用Rh（I）模型催化剂对该反应机理进行了DFT计算。
• Catalytic and Highly Regioselective Cross-Coupling of Aromatic C−H Substrates
  作者：Kami L. Hull、Melanie S. Sanford

  DOI：10.1021/ja074395z

  日期：2007.10.1

  This communication describes a new Pd-catalyzed reaction for the highly chemo- and regioselective oxidative cross-coupling of aromatic C-H bonds. This transformation is proposed to proceed via two discrete C-H activation steps whose selectivities are predominantly controlled by proximity to a ligand (first C-H activation) or by the steric environment around the arene C-H bond (second C-H activation). Furthermore, the selectivity of the second C-H activation reaction can be controlled by tuning the ligand environment around the Pd center.
• Efficient Approach To Construct Unsymmetrical Biaryls through Oxidative Coupling Reactions of Aromatic Primary Alcohols and Arylboronic Acids with a Rhodium Catalyst
  作者：Xiaobo Yu、Jingjing Wang、Weijie Guo、Yun Tian、Jianhui Wang

  DOI：10.1021/acs.organomet.6b00238

  日期：2016.6.13

  Unsymmetrical biaryls were synthesized by oxidative coupling reactions, between aromatic primary alcohols and arylboronic acids through the C-C bond cleavage of the primary alcohols chelated With a rhodium catalyst. The desired unsymmetrical biaryl products were obtained in good to excellent yields under the optimized reaction conditions. A wide variety of functionalities are compatible with the reaction under the optimized conditions. This new coupling strategy provides a favorable method to construct valuable biaryl compounds from aromatic primary alcohols which are cheap; environmentally friendly, and easily accessible substrates.
• Rhodium-Catalyzed C–H Bond Functionalization with Amides by Double C–H/C–N Bond Activation
  作者：Guangrong Meng、Michal Szostak

  DOI：10.1021/acs.orglett.6b00058

  日期：2016.2.19

  first C–H bond functionalization with amides as the coupling partners via selective activation of the amide N–C bond using rhodium(I) catalysts under highly chemoselective conditions is reported. Notably, this report constitutes the first catalytic activation of the amide N–C(O) bond by rhodium. We expect that this concept will have broad implications for using amides as coupling partners for C–H activation

  据报道，在高化学选择性条件下，使用铑（I）催化剂通过酰胺N–C键的选择性活化，首次将酰胺作为偶联伙伴进行C–H键官能化。值得注意的是，该报告构成了铑对酰胺N–C（O）键的首次催化活化。我们预计，除了本文所述的工作以外，使用酰胺作为C–H活化的偶联伴侣将具有广泛的意义。