1-(2,3-difluorophenyl)-1H-pyrrole | 195711-22-9

• 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-(2,3-difluorophenyl)-1H-pyrrole
• 英文别名: 1-(2,3-Difluorophenyl)pyrrole
• CAS: 195711-22-9
• 化学式: C₁₀H₇F₂N
• 分子量: 179.169
• InChiKey: BVZJJASLXCRPHD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• 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：
  2

反应信息

• 作为反应物：
  描述：

  1-(2,3-difluorophenyl)-1H-pyrrole 在 氢氧化钾 、 盐酸羟胺 、 sodium acetate 、 乙酸酐 、 N,N-二甲基甲酰胺 、 三氯氧磷 作用下， 以 叔丁醇 为溶剂， 反应 6.0h， 生成 4-Chloro-6-fluoropyrrolo[1,2-a]quinoxaline
  参考文献：
  名称：

  Novel and Highly Potent 5-HT₃ Receptor Agonists Based on a Pyrroloquinoxaline Structure

  摘要：

  The synthesis and the biological evaluation of a series of novel pyrroloquinoxaline derivatives are described. In binding studies several compounds proved to be potent and selective 5-HT3 receptor ligands. The most active pyrroloquinoxalines, 11d and 11e, showed a subnanomolar affinity for 5-HT3 receptor and were able to functionally discriminate the central and peripheral 5-HT3 receptors, being agonists and antagonists, respectively. In functional studies ([C-14]-guanidinium accumulation test in NG 108-15 cells, in vitro) most of the synthesized compounds showed clear-cut 5-HT3 agonist properties. In in vivo studies on the von Bezold-Jarisch reflex test (a peripheral interaction model) the behavior of the tested compounds ranged from agonist to antagonist, while clear agonist properties were obtained with 12a on cortical acetylcholine release in freely moving rats. Pharmacokinetic studies with 11e and 12c indicate that the compounds easily cross the blood-brain barrier (BBB) after systemic administration with a brain/plasma ratio of 17.5 and 37.5, respectively. Thus compounds 11e and 12c represent the most potent central 5-HT3 agonists identified to date that are able to cross the blood-brain barrier.

  DOI：

  10.1021/jm970376w
• 作为产物：
  描述：

  2,5-二甲氧基四氢呋喃 、 2,3-二氟苯胺 以 溶剂黄146 为溶剂， 反应 1.0h， 以76%的产率得到1-(2,3-difluorophenyl)-1H-pyrrole
  参考文献：
  名称：

  Novel and Highly Potent 5-HT₃ Receptor Agonists Based on a Pyrroloquinoxaline Structure

  摘要：

  The synthesis and the biological evaluation of a series of novel pyrroloquinoxaline derivatives are described. In binding studies several compounds proved to be potent and selective 5-HT3 receptor ligands. The most active pyrroloquinoxalines, 11d and 11e, showed a subnanomolar affinity for 5-HT3 receptor and were able to functionally discriminate the central and peripheral 5-HT3 receptors, being agonists and antagonists, respectively. In functional studies ([C-14]-guanidinium accumulation test in NG 108-15 cells, in vitro) most of the synthesized compounds showed clear-cut 5-HT3 agonist properties. In in vivo studies on the von Bezold-Jarisch reflex test (a peripheral interaction model) the behavior of the tested compounds ranged from agonist to antagonist, while clear agonist properties were obtained with 12a on cortical acetylcholine release in freely moving rats. Pharmacokinetic studies with 11e and 12c indicate that the compounds easily cross the blood-brain barrier (BBB) after systemic administration with a brain/plasma ratio of 17.5 and 37.5, respectively. Thus compounds 11e and 12c represent the most potent central 5-HT3 agonists identified to date that are able to cross the blood-brain barrier.

  DOI：

  10.1021/jm970376w

文献信息

• 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
• US6489480B2
  申请人：——

  公开号：US6489480B2

  公开（公告）日：2002-12-03