(η(5)-cyclopentadienyl)[1-9a-η(6)-9-fluorenone-(4'-acetyl)-anil]iron(II) hexafluorophosphate | 186774-36-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 英文名称: (η(5)-cyclopentadienyl)[1-9a-η(6)-9-fluorenone-(4'-acetyl)-anil]iron(II) hexafluorophosphate
• 英文别名: (η(5)-cyclopentadienyl)[(1,2,3,4,4a,9a-η(6))-fluorenone-(4'-methylcarbonyl)-anil]iron(II) hexafluorophosphate；cyclopenta-1,3-diene;1-[4-(fluoren-9-ylideneamino)phenyl]ethanone;iron(2+);hexafluorophosphate
• CAS: 186774-36-7
• 化学式: C₂₆H₂₀FeNO*F₆P
• 分子量: 563.262
• InChiKey: VXIGTGDKRFNFEC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.82
• 重原子数：
  36
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.04
• 拓扑面积：
  29.4
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  ammonium hexafluorophosphate 、 (η(5)-cyclopentadienyl)[1-9a-η(6)-9-fluorenone-(4'-acetyl)-anil]iron(II) hexafluorophosphate 以 further solvent(s) 为溶剂， 以81%的产率得到(η(5)-cyclopentadienyl)[1-9a-η(6)-9-(4'-acetylphenylamino)fluorene]iron(II) hexafluorophosphate
  参考文献：
  名称：

  Electrochemical reduction of some [(η5-Cyclopentadienyl) (η6-arene) iron(II)][PF6] complexes bearing an imine or a nitrone function in benzylic position of the arene ligand

  摘要：

  The electrochemical reduction in basic hydro-organic media of mixtures of [(eta(5)-Cp) (eta(6)-benzophenone-N-(aryl)nitrone) Fe](+) 1a-d and [(eta(5)-Cp) (eta(6)-benzophenone anil) Fe](+) complexes 1'a-d led to the corresponding [(eta(5)-Cp) (eta(6)-alpha-(arylamino)diphenylmethane) Fe](+) cations 2a-d with good yields (85-90%). In a similar manner, various [(eta(5)-Cp) (eta(6)-9-(arylamino)fluorene) Fe](+) cations 4a-i were synthesized (70-88% yield) in acidic hydro-organic media from the corresponding [(eta(5)-Cp) (eta(6)-fluorenone anil) Fe](+) 3a-i or the [(eta(5)-Cp) (eta(6)-fluorenone-N-(2'-methoxycarbonyl phenyl)nitrone) Fe](+) derivative 3'i. According to H-1 NMR chemical shifts, the exo isomer is formed in the majority (exo:endo ca. 75:25) during electrosynthesis of compounds 4a-i. We could explain these unexpected results by an epimerization in the electrolysis media. The amines 4a,b were re-oxidized by oxygen into the starting imine 3a,b under very mild Al2O3-catalysis conditions (77-80% yield). (C) 1998 Elsevier Science S.A.

  DOI：

  10.1016/s0022-328x(97)00627-x
• 作为产物：
  描述：

  (η(5)-cyclopentadienyl)(η(6)-fluorene)iron(II) hexafluororophosphate 、 1-(4-亚硝基苯基)乙酮 在 t-BuOK 作用下， 以 四氢呋喃 为溶剂， 生成 (η(5)-cyclopentadienyl)[1-9a-η(6)-9-fluorenone-(4'-acetyl)-anil]iron(II) hexafluorophosphate
  参考文献：
  名称：

  Synthesis, structure and hydrolysis of some [(η5-cyclopentadienyl)(η6-arene) iron(II)][PF6] complexes bearing an imine or a nitrone function in α-position of the arene ligand

  摘要：

  Condensation between [(eta(5)-Cp)(eta(6)-fluorene)Fe](+)] I and various nitrosoarenes R-Ph-NO (R = H, 2-Me, 3-Me, 4-Me, 3-COMe, 4-COMe and 4-NMe(2)) were initiated with 5% t-BuOK and led to [(eta(5)-Cp)(eta(6)-fluorenone-anil)Fe](+) complexes Ia-g (57-88%) as syn-anti mixtures (ca. 30:70 respectively). [(eta(5)-Cp)(eta(6)-diphenylmethane)Fe](+) II with nitrosobenzene or nitrosotoluenes gave mixtures of [(eta(5)-Cp)(eta(6)-benzophenone-N-phenylnitrone)Fe](+) IIa-d and [(eta(5)-Cp)(eta(6)-benzophenone-anil)Fe](+) IIa-d complexes (ca. 80:20) with good yields (80-92%). Nitrone complexes IIa,e,d were isolated as pure Z-isomer by fractional recrystallisation (22-35%). 2D-H-1, C-13 NMR correlation and X-ray analysis were used to identify the new compounds. Owing to the high nitrosobenzene oxidative character, condensation with other [(eta(5)-Cp)(eta(6)-arene)Fe](+) complexes (arene = toluene, ethylbenzene, indane and tetraline) failed. Acidic hydrolysis of these imine and nitrone complexes has been investigated kinetically using polarography. Macroscale hydrolysis yielded [eta(5)-Cp)(eta(6)-fluorenone)Fe](+) Ii (82%) and [(eta(5)-Cp)(eta(6)-benzophenone)Fe](+) IIi (91%).

  DOI：

  10.1016/s0022-328x(96)06632-6