1-(perfluorophenyl)-1H-indole | 344452-99-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: 1-(perfluorophenyl)-1H-indole
• 英文别名: 1-(pentafluorophenyl)indole；1-(2,3,4,5,6-Pentafluorophenyl)indole
• CAS: 344452-99-9
• 化学式: C₁₄H₆F₅N
• 分子量: 283.2
• InChiKey: XJYYXCANPCKQJN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  20
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  4.9
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  吲哚 、 六氟苯 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 5.0h， 生成 1-(perfluorophenyl)-1H-indole 、 1,1'-(perfluoro-1,4-phenylene)bis(1H-indole)
  参考文献：
  名称：

  由K [C 6 F 5 BF 3 ]和碱金属azol-1-ide合成4-（1-azol-1-yl）-2,3,5,6-四氟苯基三氟硼酸钾。碱金属azol-1-ides和二烷基酰胺在亲核性上的显着区别

  摘要：

  在60-130°C的极性非质子溶剂（DMF，DMSO）中，用碱金属氮杂-1-酸将K [C 6 F 5 BF 3 ]中的氟原子亲核取代，得到4-（氮杂-1-基）-钾2,3,5,6-四氟苯基三氟硼酸酯，K [4-AzC 6 F 4 BF 3 ]（AzH =吡咯，吡唑，咪唑，吲哚和苯并咪唑）。出乎意料的是，二乙胺和吗啉在相同条件下不会与K [C 6 F 5 BF 3 ]反应，而五氟苯和R 2 NC 6 F 4 H在150°C时形成。K [C 6 F 5 BF 3的反应用二甘醇二甲醚或DMSO中的Na [NR 2 ]进行类似的过程。推测的原因是仲胺和碱金属二烷基酰胺的亲核性都较低，这会导致与K [C 6 F 5 BF 3 ]的破坏性副反应，而不是其氨基脱氟。模型底物C 6 F 5 Ph与吲哚钠/吗啉化钠的竞争性亲核氨基脱氟作用证实了这一点。

  DOI：

  10.1016/j.jfluchem.2013.07.011

文献信息

• Selective C4–F bond cleavage of pentafluorobenzene: synthesis of N-tetrafluoroarylated heterocyclic compounds
  作者：Cuibo Liu、Huan Wang、Xing Xing、You Xu、Jun-An Ma、Bin Zhang

  DOI：10.1016/j.tetlet.2013.06.055

  日期：2013.8

  A simple aromatic nucleophilic monosubstitution reaction for the synthesis of N-tetrafluoroarylated heterocyclic compounds via selective C4–F bond cleavage of pentafluorobenzene with N–H containing heterocycles is demonstrated. This method is highly tolerant of a wide range of substrates to give the corresponding products in moderate to good yields. Additionally, this strategy is applied to synthesize

  展示了一种简单的芳香亲核单取代反应，该反应可通过五氟苯与含N–H的杂环的选择性C4-F键裂解来合成N-四氟芳基杂环化合物。该方法高度耐受各种底物，从而以中等至良好的产率获得相应的产物。另外，该策略适用于合成其他单氟，二氟和三氟芳基化的吲哚衍生物。
• Olefin polymerization cocatalysts derived from group-15 cationic compounds and processes using them
  申请人：ExxonMobil Chemical Patents Inc.

  公开号：EP1661900A1

  公开（公告）日：2006-05-31

  Fluorinated amine compounds, R'iArF-ER2, where ArF is a fluo-roaryl substituent, E is nitrogen or phosphorous, each R is independently a C1-C20 hydrocarbyl substituent, or the two R's may be connected to form an unsubstituted or substituted C2-C20 cycloaliphatic substituent, R' is a C1-C20 hydrocarbyl or halogenated hydrocarbyl, and i is 0, 1 or 2 are disclosed. These compounds may be protonated and complexed with suitable substantially noncoordinating anions to prepare polymerization catalyst components. When these catalyst components are combined with organometallic catalyst precursors, the catalyst precursor is activated to a catalyst. This catalyst is combined with monomer under olefin polymerization conditions to prepare polymer. High number-average molecular weight polymers at high productivity rates were observed from using metallocene catalysts activated with [N-pentafluorophenyl pyrrolidinium] [tetrakis(pentafluorophenyl) borate].

  本发明公开了氟化胺化合物 R'iArF-ER2，其中 ArF 为氟芳基取代基，E 为氮或磷，每个 R 独立为 C1-C20 碳氢基取代基，或两个 R 连接形成未取代或取代的 C2-C20 环脂族取代基，R'为 C1-C20 碳氢基或卤代碳氢基，i 为 0、1 或 2。这些化合物可以质子化并与适当的基本不配位阴离子络合，制备聚合催化剂组分。当这些催化剂组分与有机金属催化剂前体结合时，催化剂前体被活化成催化剂。催化剂在烯烃聚合条件下与单体结合，制备聚合物。使用[N-五氟苯基吡咯烷][四(五氟苯基)硼酸酯]活化的茂金属催化剂可以观察到高生产率下的高平均分子量聚合物。
• GROUP-15 CATIONIC COMPOUNDS FOR OLEFIN POLYMERIZATION CATALYSTS
  申请人：——

  公开号：US20020111265A1

  公开（公告）日：2002-08-15

  This description addresses fluorinated amine compounds meeting the general formula R′ i ArF-ER 2 , where ArF is a fluoroaryl group, E is nitrogen or phosphorous, each R is independently a C 1 -C 20 hydrocarbyl group, or the two Rs may connect to form an unsubstituted or substituted C 2 -C 20 cycloaliphatic group, R′ is a C 1 -C 20 hydrocarbyl or halogenated hydrocarbyl, and i is 0, 1 or 2. These compounds may be protonated with strong Bronsted acids to form protonated amine compounds that are useful for the preparation of organometallic catalyst-cocatalyst compounds comprising noncoordinating or weakly coordinating anions. The resulting organometallic catalyst-cocatalyst complexes can be effectively used as olefin polymerization catalysts. High number-average molecular weight polymers at high rates of productivity were observed from the use of metallocene catalyst complexes prepared with [N-pentafluorophenyl pyrrolidinium][tetrakis(pentafluorophenyl)borate] of [N-pentafluorophenyl pyrrolidinium][chloride].

  本说明涉及符合通式 R′ 的氟化胺化合物 i ArF-ER 2 其中 ArF 是氟芳基，E 是氮或磷，每个 R 独立地是 C 1 -C 20 烃基，或两个 R 可连接形成未取代或取代的 C 2 -C 20 环脂族基团，R′是一个 C 1 -C 20 烃基或卤代烃基，i 为 0、1 或 2。这些化合物可以用强勃朗斯特酸质子化，形成质子化胺化合物，用于制备包含非配位或弱配位阴离子的有机金属催化剂-催化剂化合物。由此得到的有机金属催化剂-催化剂复合物可有效地用作烯烃聚合催化剂。使用 [N-pentafluorophenyl pyrrolidinium][tetrakis(pentafluorophenyl)borate] of [N-pentafluorophenyl pyrrolidinium][chloride] 制备的茂金属催化剂络合物，可以观察到生产率高的高平均分子量聚合物。
• Olefin polymerization catalysts derived from Group-15 cationic compounds and processes using them
  申请人：——

  公开号：US20020115806A1

  公开（公告）日：2002-08-22

  Fluorinated amine compounds, R′ i ArF-ER 2 , where ArF is a fluoroaryl substituent, E is nitrogen or phosphorous, each R is independently a C 1 -C 20 hydrocarbyl substituent, or the two R's may be connected to form an unsubstituted or substituted C 2 -C 20 cycloaliphatic substituent, R′ is a C 1 -C 20 hydrocarbyl or halogenated hydrocarbyl, and i is 0, 1 or 2 are disclosed. These compounds may be protonated and complexed with suitable substantially noncoordinating anions to prepare polymerization catalyst components. When these catalyst components are combined with organometallic catalyst precursors, the catalyst precursor is activated to a catalyst. This catalyst is combined with monomer under olefin polymerization conditions to prepare polymer. High number-average molecular weight polymers at high productivity rates were observed from using metallocene catalysts activated with [N-pentafluorophenyl pyrrolidinium][tetrakis(pentafluorophenyl)borate].

  氟化胺化合物，R′ i i ArF-ER 2 其中 ArF 是氟芳基取代基，E 是氮或磷，每个 R 独立地是 C 1 -C 20 烃基取代基，或者两个 R 可以连接形成未取代或取代的 C 2 -C 20 环脂族取代基，R′是 C 1 -C 20 烃基或卤代烃基，i 为 0、1 或 2。这些化合物可以质子化并与合适的基本上不配位的阴离子络合，制备聚合催化剂组分。当这些催化剂组分与有机金属催化剂前体结合时，催化剂前体被活化成催化剂。催化剂在烯烃聚合条件下与单体结合，制备聚合物。使用经 N-五氟苯基吡咯烷硼酸酯和四(五氟苯基)硼酸酯活化的茂金属催化剂，可以观察到生产率高、平均分子量高的聚合物。
• OLEFIN POLYMERIZATION COCATALYSTS DERIVED FROM GROUP-15 CATIONIC COMPOUNDS AND PROCESSES USING THEM
  申请人：EXXON CHEMICAL PATENTS INC.

  公开号：EP1252166A1

  公开（公告）日：2002-10-30