N-(perfluorophenyl)pyrrolidine | 15368-84-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 英文名称: N-(perfluorophenyl)pyrrolidine
• 英文别名: 1-(perfluorophenyl)pyrrolidine；N-pentafluorophenylpyrrolidine；1-(2,3,4,5,6-Pentafluorophenyl)pyrrolidine
• CAS: 15368-84-0
• 化学式: C₁₀H₈F₅N
• 分子量: 237.172
• InChiKey: KAIHLIZGJKDPGB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  3.2
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  四氢吡咯 、 溴五氟苯 在 C₃₄H₂₄N₂O₂ 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 以93%的产率得到N-(perfluorophenyl)pyrrolidine
  参考文献：
  名称：

  基于吩嗪的施主受体系统作为“无金属” CN / CC交叉偶联的有机光催化剂。

  摘要：

  为了在供体受体系统的基态和激发态还原电位之间实现平衡，以实现有效的C–N / C–C交叉耦合，通过改变供体，合成了一系列供体受体系统DA1-DA4。强度和连​​接位置。随着施主强度的增加，观察到基态还原电位的系统升高和HOMO-LUMO间隙的减小。有趣的是，所有衍生物DA1-DA4都可以在无金属条件下以低催化负载催化活化的芳基卤化物和胺之间的C-N键形成反应，而无需在白色LED照射下使用任何外部碱。在派生DA2的情况下实现了平衡，在C–N联轴器中表现出很高的效率。不同的控制实验支持可见光介导的C–N键形成过程中能量以及电子转移途径的有效性。这项研究进一步揭示了衍生物DA1在涉及活化芳基卤化物的“无金属” Sonogashira偶联中的潜力，这归因于其高激发态还原电位。

  DOI：

  10.1021/acs.joc.9b03407

文献信息

• Magnesium-mediated arylation of amines <i>via</i> C–F bond activation of fluoroarenes
  作者：Leonie J. Bole、Laia Davin、Alan R. Kennedy、Ross McLellan、Eva Hevia

  DOI：10.1039/c9cc01670h

  日期：——

  Exploiting the high nucleophilic power of structurally defined β-diketiminate stabilised magnesium amides, a new method for amine arylation via rapid C–F bond activation of fluoroarenes is introduced.

  利用结构明确定的β-二酮亚胺稳定的镁胺的高亲核能力，引入了一种通过快速活化氟芳烃的C-F键实现胺芳基化的新方法。
• 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。
• Nitrogen-containing group-13 anionic compounds for olefin polymerization
  申请人：——

  公开号：US20030083515A1

  公开（公告）日：2003-05-01

  The invention addresses an composition of matter comprising a cation [Ct] + and an anion [A] − , the anion comprises a core Group-13 element bound to partially or completely fluorinated fluoroaryl ligands, at least one of the fluoroaryl ligands is substituted with a Group-15 element that has been rendered essentially inert for subsequent chemical reaction through its unbonded electron pair by substituting an electron-withdrawing group on it. [Ct] + may be selected from anilinium and ammonium cations, trityl carbenium cations, Group-11 metal cations, silylium cations, the cations of the hydrated salts of Group-1 or -2 metals, and derivatives of the foregoing anilinium, ammonium, trityl carbenium, and silylium cations containing C 1 -C 20 hydrocarbyl, hydrocarbylsilyl, or hydrocarbylamine substituents for one or more hydrogen atoms of said cations. The compositions can be used to activate olefin polymerization catalysts, and can be prepared to dissolve in aliphatic solvents. Syntheses and polymerization are illustrated.

  本发明涉及一种由阳离子 [Ct&rsqb； 和阴离子 和阴离子 [A&rsqb； - 其中阴离子包括与部分或完全氟化的氟芳基配位体结合的核心 13 族元素，氟芳基配位体中至少有一个被 15 族元素取代，该 15 族元素通过取代其上的无键电子对上的一个吸电子基团而使其在随后的化学反应中基本呈惰性； &plus； 可选自氨和铵阳离子、氨三苄阳离子、第 11 族金属阳离子、水铵阳离子、第 1 或第 2 族金属的水合盐阳离子，以及上述氨、铵、氨三苄和水铵阳离子的衍生物，这些衍生物含有 C 1 -C 20 烃基、烃基硅基或烃基胺取代基的阳离子衍生物。这些组合物可用于活化烯烃聚合催化剂，并能溶解在脂肪族溶剂中。图解说明了合成和聚合过程。