2-(4,4-二氟-2-甲基丁-3-烯-2-基)苯基三氟甲磺酸酯 | 928828-70-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 2-(4,4-二氟-2-甲基丁-3-烯-2-基)苯基三氟甲磺酸酯
• 英文名称: 2-(4,4-difluoro-2-methylbut-3-en-2-yl)phenyl trifluoromethanesulfonate
• 英文别名: [2-(4,4-Difluoro-2-methylbut-3-en-2-yl)phenyl] trifluoromethanesulfonate；[2-(4,4-difluoro-2-methylbut-3-en-2-yl)phenyl] trifluoromethanesulfonate
• CAS: 928828-70-0
• 化学式: C₁₂H₁₁F₅O₃S
• 分子量: 330.276
• InChiKey: JHAWZBIRHHHSAI-UHFFFAOYSA-N

物化性质

• 沸点：
  310.7±42.0 °C(Predicted)
• 密度：
  1.385±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  51.8
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  2-(4,4-二氟-2-甲基丁-3-烯-2-基)苯基三氟甲磺酸酯 在 四(三苯基膦)钯 、 三苯基膦 、 phosphate buffer 作用下， 以 N,N-二甲基乙酰胺 为溶剂， 反应 9.0h， 以57%的产率得到3,3-二甲基-2,3-二氢-1H-茚-1-酮
  参考文献：
  名称：

  Heck-type 5-endo-trig cyclizations promoted by vinylic fluorines: Ring-fluorinated indene and 3H-pyrrole syntheses from 1,1-difluoro-1-alkenes

  摘要：

  Arylpalladium or aminopalladium species bearing a 2,2-difluorovinyl group undergo an unusual 5-endo alkene insertion followed by beta-fluorine elimination. These processes provide a facile access to ring-fluorinated five-membered carbocyclic and heterocyclic compounds starting from an o-(3,3-difluoroallyl)phenyl trifluoromethanesulfonate and 3,3-difluoroallyl ketone O-pentafluorobenzoyloximes. In both systems, the two vinylic fluorine atoms are essential for Heck-type 5-endo-trig cyclizations. (C) 2006 Elsevier B.V All rights reserved.

  DOI：

  10.1016/j.jfluchem.2005.12.023
• 作为产物：
  描述：

  2-(4,4-difluoro-2-methylbut-3-en-2-yl)phenol 、 三氟甲磺酸酐 在 吡啶 作用下， 反应 32.0h， 以80%的产率得到2-(4,4-二氟-2-甲基丁-3-烯-2-基)苯基三氟甲磺酸酯
  参考文献：
  名称：

  Heck-type 5-endo-trig cyclizations promoted by vinylic fluorines: Ring-fluorinated indene and 3H-pyrrole syntheses from 1,1-difluoro-1-alkenes

  摘要：

  Arylpalladium or aminopalladium species bearing a 2,2-difluorovinyl group undergo an unusual 5-endo alkene insertion followed by beta-fluorine elimination. These processes provide a facile access to ring-fluorinated five-membered carbocyclic and heterocyclic compounds starting from an o-(3,3-difluoroallyl)phenyl trifluoromethanesulfonate and 3,3-difluoroallyl ketone O-pentafluorobenzoyloximes. In both systems, the two vinylic fluorine atoms are essential for Heck-type 5-endo-trig cyclizations. (C) 2006 Elsevier B.V All rights reserved.

  DOI：

  10.1016/j.jfluchem.2005.12.023

文献信息

• Heck-type 5-endo-trig cyclizations promoted by vinylic fluorines: Ring-fluorinated indene and 3H-pyrrole syntheses from 1,1-difluoro-1-alkenes
  作者：Junji Ichikawa、Kotaro Sakoda、Jun Mihara、Naotaka Ito

  DOI：10.1016/j.jfluchem.2005.12.023

  日期：2006.5

  Arylpalladium or aminopalladium species bearing a 2,2-difluorovinyl group undergo an unusual 5-endo alkene insertion followed by beta-fluorine elimination. These processes provide a facile access to ring-fluorinated five-membered carbocyclic and heterocyclic compounds starting from an o-(3,3-difluoroallyl)phenyl trifluoromethanesulfonate and 3,3-difluoroallyl ketone O-pentafluorobenzoyloximes. In both systems, the two vinylic fluorine atoms are essential for Heck-type 5-endo-trig cyclizations. (C) 2006 Elsevier B.V All rights reserved.