1-benzoylcyclohexane-1-carbaldehyde

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-benzoylcyclohexane-1-carbaldehyde
• 化学式: C₁₄H₁₆O₂
• 分子量: 216.28
• InChiKey: KHIONUGZBFDPIQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  34.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-benzoylcyclohexane-1-carbaldehyde 、 二溴二氟甲烷 在 4 A molecular sieve 、 三(二甲胺基)膦 作用下， 以 四氢呋喃 为溶剂， 反应 10.5h， 生成 [1-(2,2-difluorovinyl)cyclohexyl]phenylmethanone
  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：

  4-(cyclohexylidenemethyl)morpholine 、 苯甲酰氯 在 碳酸氢钠 作用下， 以 乙醚 为溶剂， 反应 4.0h， 以46%的产率得到1-benzoylcyclohexane-1-carbaldehyde
  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.