2-heptafluoropropylindole | 123825-50-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: 2-heptafluoropropylindole
• 英文别名: 2-(perfluoropropyl)-1H-indole；2-(Heptafluoropropyl)-1H-indole；2-(1,1,2,2,3,3,3-heptafluoropropyl)-1H-indole
• CAS: 123825-50-3
• 化学式: C₁₁H₆F₇N
• 分子量: 285.164
• InChiKey: SWGJHJPLSVAHJS-UHFFFAOYSA-N

物化性质

• 熔点：
  63-64 °C
• 沸点：
  254.7±40.0 °C(Predicted)
• 密度：
  1.498±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  15.8
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  bis(heptafluorobutyryl) peroxide 生成 2-heptafluoropropylindole
  参考文献：
  名称：

  KAMIKATA, NOBUMASA;JOSIDA, MASAXITO;SAVADA, XIDEHO;NAKAYAMA, MASAAKI

  摘要：

  DOI：

文献信息

• Palladium-Catalyzed C2-Regioselective Perfluoroalkylation of the Free (NH)-Heteroarenes
  作者：Hong Qin、Jie Zhang、Kai Qiao、Dong Zhang、Wei He、Chengkou Liu、Zheng Fang、Kai Guo

  DOI：10.1021/acs.joc.0c02782

  日期：2021.2.5

  A highly regioselective and atom-efficient strategy for the construction of fused free (NH) heteroarenes through a palladium-catalyzed perfluoroalkyl insertion reaction has been accomplished. This protocol employed multiple iodofluoroalkanes as practical and available perfluoroalkyl sources to provide an operationally simple and versatile route for the synthesis of perfluoroalkylated indoles. Moreover

  已经实现了通过钯催化的全氟烷基插入反应构建稠合的游离（NH）杂芳烃的高度区域选择性和原子效率高的策略。该方案采用多种碘氟烷烃作为实用和可用的全氟烷基来源，为合成全氟烷基化的吲哚提供了操作上简单而通用的途径。此外，没有指导小组协助的吲哚被用作底物，实现了吲哚的C（sp 2）–H位点选择性官能化，收率高达95％。此外，该协议还用于生物活性化合物（如植物生长素，色氨酸和褪黑激素类似物）的后期C2全氟烷基化。
• A New and Efficient One-Pot Synthesis of 2-Fluoroalkyl Substituted Indoles
  作者：Zengxue Wang、Qingwen Ma

  DOI：10.1002/jhet.2290

  日期：2015.11

  A new simple and efficient one‐pot synthesis of 2‐fluoroalkyl substituted indoles from 2‐aminobenzyl alcohols with fluorine‐containing carboxylic acids in the presence of Ph3P, CCl4, and NEt3 is described. Various kinds of 2‐fluoroalkyl substituted indole derivatives can be conveniently prepared.

  描述了在Ph 3 P，CCl 4和NEt 3存在下，由2-氨基苄醇与含氟羧酸简单，有效地单反应合成2-氟烷基取代的吲哚的方法。可以方便地制备各种2-氟烷基取代的吲哚衍生物。
• Synthesis of perfluoroalkylpyrroles by homolytic substitution with perfluoroalkyl radicals
  作者：Enrico Baciocchi、Ester Muraglia

  DOI：10.1016/s0040-4039(00)79233-1

  日期：1993.6

  An efficient synthesis of perfluoroalkylpyrroles has been performed by reaction of pyrroles and some derivatives with perfluoroalkyl radicals generated by perfluoroalkyl iodides/ H2O2/ Fe+2 in DMSO at room temperature.

  通过吡咯和一些衍生物与全氟烷基碘化物/ H 2 O 2 / Fe +2在室温下由全氟烷基产生的全氟烷基自由基的反应，可以进行全氟烷基吡咯的有效合成。
• Bromotriphenylphosphonium Salt Promoted One-Pot Cyclization to 2-Fluoroalkyl-Substituted Indoles
  作者：Zeng-xue Wang、Tai-feng Zhang、Qing-wen Ma、Wei-gui Ni

  DOI：10.1055/s-0034-1379030

  日期：——

  2-Fluoroalkyl-substituted indoles were prepared in moderate to excellent yields through bromotriphenylphosphonium salt promoted ring formation with fluorine-containing carboxylic acids in the presence of triethylamine in toluene at reflux temperature. A range of 2-fluoroalkyl-substituted indole derivatives can be conveniently prepared.
• Yoshida, Masato; Yoshida, Tatsuro; Kobayashi, Michio, Journal of the Chemical Society. Perkin transactions I, 1989, p. 909 - 914
  作者：Yoshida, Masato、Yoshida, Tatsuro、Kobayashi, Michio、Kamigata, Nobumasa

  DOI：——

  日期：——