1-[2-oxo-2-(perfluorophenyl)ethyl]pyridinium bromide | 1046768-16-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-[2-oxo-2-(perfluorophenyl)ethyl]pyridinium bromide
• 英文别名: 1-(2,3,4,5,6-Pentafluorophenyl)-2-pyridin-1-ium-1-ylethanone;bromide
• CAS: 1046768-16-4
• 化学式: Br*C₁₃H₇F₅NO
• 分子量: 368.101
• InChiKey: WCYNLGSIOVMTNP-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  -0.44
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  21
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  1-[2-oxo-2-(perfluorophenyl)ethyl]pyridinium bromide 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以96%的产率得到(1-pyridinio)perfluorophenacylide
  参考文献：
  名称：

  (1-Pyridinio)perfluorophenacylide: a new stable pyridinium ylide in the enol form

  摘要：

  The title compound, C13H6F5NO, exists in the enol form and adopts the E configuration about the enol double bond. It is the first example of an enol-type pyridinium ylide. The enol structure was unambiguously determined on the basis of the significantly longer C - O bond and shorter C - C bond. Intramolecular C - H center dot center dot center dot O and C - H center dot center dot center dot F hydrogen bonds are responsible for promotion of the enol form and for the stability of this compound.

  DOI：

  10.1107/s0108270108006318

文献信息

• An Unusual Reaction of a Pyridinium Ylide with 1,1-Dicyanoethylene Derivatives
  作者：Shinji Yamada、Emiko Ohta

  DOI：10.1246/cl.2008.628

  日期：2008.6.5

  A reaction of pyridinium perfluorophenacylide generated from pyridinium salt 1 with 1,1-dicyanoethylene derivatives 2 produced unusual products 3, which have an ylide structure with a cyano group at the C2 and a cis-acrylonitrile moiety at the o-position of the perfluorophenyl group. A plausible mechanism involving intramolecular aromatic nucleophilic substitution and 1,3-migration of the cyano group is proposed for this reaction.

  由吡啶鎓盐 1 生成的全氟苯甲酰基吡啶鎓与 1,1-二氰基乙烯衍生物 2 反应生成不寻常的产物 3，其具有叶立德结构，C2 处有氰基，全氟苯基的邻位有顺式丙烯腈部分。该反应提出了一种涉及分子内芳香亲核取代和氰基 1,3-迁移的合理机制。
• (1-Pyridinio)perfluorophenacylide: a new stable pyridinium ylide in the enol form
  作者：Shinji Yamada、Emiko Ohta

  DOI：10.1107/s0108270108006318

  日期：2008.4.15

  The title compound, C13H6F5NO, exists in the enol form and adopts the E configuration about the enol double bond. It is the first example of an enol-type pyridinium ylide. The enol structure was unambiguously determined on the basis of the significantly longer C - O bond and shorter C - C bond. Intramolecular C - H center dot center dot center dot O and C - H center dot center dot center dot F hydrogen bonds are responsible for promotion of the enol form and for the stability of this compound.