(E)-2-(2,2-difluorovinyl)-2-methyl-3,4-dihydro-2H-naphthalen-1-one O-pentafluorobenzoyloxime

• 分子结构分类: 有机化合物 - 苯类化合物 - 四氢化萘
• 英文名称: (E)-2-(2,2-difluorovinyl)-2-methyl-3,4-dihydro-2H-naphthalen-1-one O-pentafluorobenzoyloxime
• 英文别名: [(E)-[2-(2,2-difluoroethenyl)-2-methyl-3,4-dihydronaphthalen-1-ylidene]amino] 2,3,4,5,6-pentafluorobenzoate
• 化学式: C₂₀H₁₂F₇NO₂
• 分子量: 431.31
• InChiKey: CGADREVQEVQPPA-VEILYXNESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  30
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  38.7
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为产物：
  描述：

  2-(2,2-difluorovinyl)-2-methyl-3,4-dihydro-2H-naphthalen-1-one oxime 、 五氟苯甲酰氯 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 生成 (Z)-2-(2,2-difluorovinyl)-2-methyl-3,4-dihydro-2H-naphthalen-1-one O-pentafluorobenzoyloxime 、 (E)-2-(2,2-difluorovinyl)-2-methyl-3,4-dihydro-2H-naphthalen-1-one O-pentafluorobenzoyloxime
  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.