5,6-bis(4-fluorophenyl)indolo[1,2-a]quinoline | 1185863-96-0

• 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
• 英文名称: 5,6-bis(4-fluorophenyl)indolo[1,2-a]quinoline
• CAS: 1185863-96-0
• 化学式: C₂₈H₁₇F₂N
• 分子量: 405.446
• InChiKey: RHYYKHABFFRSIQ-UHFFFAOYSA-N

物化性质

• 沸点：
  504.5±50.0 °C(predicted)
• 密度：
  1.23±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7.8
• 重原子数：
  31
• 可旋转键数：
  2
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  4.4
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  3-(1,3-dioxolan-2-yl)-1-phenyl-1H-indole 在 盐酸 、 正丁基锂 、 dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer 、 copper diacetate 、 cesium pivalate 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 正己烷 、 水 、 丙酮 为溶剂， 反应 24.0h， 生成 5,6-bis(4-fluorophenyl)indolo[1,2-a]quinoline
  参考文献：
  名称：

  Aldehyde as a Traceless Directing Group for Rh(III)-Catalyzed C–H Activation: A Facile Access to Diverse Indolo[1,2-a]quinolines

  摘要：

  The aldehyde group has been developed for the first time as a traceless directing group to promote regioselective Rh(III)-catalyzed C-H activation/cyclization of indolyl aldehydes with alkynes. This protocol streamlines access to a variety of appealing indolo[1,2-a]quinoline structures. As illustrative examples, a concise three-step synthesis of indolo[1,2-a]quinoline-based sensitizers is accomplished that exhibits the potential of C-H activation in the construction of organic optoelectronic materials.

  DOI：

  10.1021/acs.orglett.5b01171

文献信息

• Fused Ring Construction around Pyrrole, Indole, and Related Compounds via Palladium-Catalyzed Oxidative Coupling with Alkynes
  作者：Mana Yamashita、Hakaru Horiguchi、Koji Hirano、Tetsuya Satoh、Masahiro Miura

  DOI：10.1021/jo9016698

  日期：2009.10.2

  palladium-catalyzed oxidative coupling reactions of N-substituted indoles or their carboxylic acid derivatives with alkynes. Unsymmetrically octasubstituted carbazoles can also be obtained by the stepwise couplings of 1-methylpyrrole-2-carboxylic acid with two different alkynes. In addition, the present coupling procedure is applicable to the synthesis of other various heteroarenes possessing di-, tri-, and tetracyclic

  1,2,3,4-四取代咔唑的选择性合成可以通过钯取代的N-取代的吲哚或其羧酸衍生物与炔烃的氧化偶联反应来有效地进行。不对称的八取代咔唑也可以通过1-甲基吡咯-2-羧酸与两种不同炔烃的逐步偶联获得。另外，本偶联方法适用于具有二，三和四环核的其他各种杂芳烃的合成。一些产品在固态下表现出强烈的荧光。
• Nickel-Catalyzed Cyclization Strategy for the Synthesis of Pyrroloquinolines, Indoloquinolines, and Indoloisoquinolines
  作者：Sampath Thavaselvan、Kanniyappan Parthasarathy

  DOI：10.1021/acs.orglett.0c01055

  日期：2020.5.15

  An inexpensive and benchtop stable Ni-catalyst/Zn system for the synthesis of pyrrolo/indoloquinolines and indolo[2,1-a]isoquinolines is explored. This platform provides a one-pot entry for the preparation of various pyrrolo and indoloquinolines/isoquinolines, which involves successive C-C and C-N bond formation, respectively. In addition, we have also performed the preliminary photophysical studies

  探索了一种廉价且台式稳定的镍催化剂/锌体系，用于合成吡咯并/吲哚并喹啉和吲哚并[2,1-a]异喹啉。该平台为制备各种吡咯啉和吲哚喹啉/异喹啉提供了一个一站式方法，分别涉及连续的CC和CN键形成。此外，我们还对合成的化合物进行了初步的光物理研究。
• Aldehyde as a Traceless Directing Group for Rh(III)-Catalyzed C–H Activation: A Facile Access to Diverse Indolo[1,2-<i>a</i>]quinolines
  作者：Xingyan Liu、Xiaoyu Li、Hu Liu、Qiang Guo、Jingbo Lan、Ruilin Wang、Jingsong You

  DOI：10.1021/acs.orglett.5b01171

  日期：2015.6.19

  The aldehyde group has been developed for the first time as a traceless directing group to promote regioselective Rh(III)-catalyzed C-H activation/cyclization of indolyl aldehydes with alkynes. This protocol streamlines access to a variety of appealing indolo[1,2-a]quinoline structures. As illustrative examples, a concise three-step synthesis of indolo[1,2-a]quinoline-based sensitizers is accomplished that exhibits the potential of C-H activation in the construction of organic optoelectronic materials.