3,3-diferrocenylcyclopropene | 500213-91-2

• 分子结构分类: 有机化合物 - 碳氢化合物 - 芳香烃
• 英文名称: 3,3-diferrocenylcyclopropene
• 英文别名: cyclopenta-1,3-diene;5-(1-cyclopenta-2,4-dien-1-ylcycloprop-2-en-1-yl)cyclopenta-1,3-diene;iron(2+)
• CAS: 500213-91-2
• 化学式: C₂₃H₂₀Fe₂
• 分子量: 408.106
• InChiKey: VXKIGCLZVFANRU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.79
• 重原子数：
  25
• 可旋转键数：
  0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.04
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3,3-diferrocenylcyclopropene 以 苯 为溶剂， 以15%的产率得到1,1-diferrocenylpropene
  参考文献：
  名称：

  3,3-Diferrocenylcyclopropene

  摘要：

  Dehydrohalogenation of isomeric 2-chloro- and 2-bromo-1,1-diferrocenyleyclopropanes (Z- and E-isomers with respect to the 'bisecting' ferrocenyl substituent) under the action of Bu'OK in DMSO afforded 3,3-diferrocenylcyclopropene. In solution, this underwent facile opening of the small ring to give 3-ferrocenyl-1H-cyclopentaferrocene ( similar to 55%) and 1,1-diferrocenylpropene (15%). The spatial structure of Z-2-chloro-1,1-diferrocenylcyclopropane and 1,1-diferrocenylcyclopropane were elucidated by X-ray diffraction analysis of a single crystal. (C) 2002 Elsevier Science B.V. All rights reserved.

  DOI：

  10.1016/s0022-328x(02)01702-3
• 作为产物：
  描述：

  E-2-chloro-1,1-diferrocenylcyclopropane 在 t-BuOK 作用下， 以 二甲基亚砜 为溶剂， 以18%的产率得到3,3-diferrocenylcyclopropene
  参考文献：
  名称：

  3,3-Diferrocenylcyclopropene

  摘要：

  Dehydrohalogenation of isomeric 2-chloro- and 2-bromo-1,1-diferrocenyleyclopropanes (Z- and E-isomers with respect to the 'bisecting' ferrocenyl substituent) under the action of Bu'OK in DMSO afforded 3,3-diferrocenylcyclopropene. In solution, this underwent facile opening of the small ring to give 3-ferrocenyl-1H-cyclopentaferrocene ( similar to 55%) and 1,1-diferrocenylpropene (15%). The spatial structure of Z-2-chloro-1,1-diferrocenylcyclopropane and 1,1-diferrocenylcyclopropane were elucidated by X-ray diffraction analysis of a single crystal. (C) 2002 Elsevier Science B.V. All rights reserved.

  DOI：

  10.1016/s0022-328x(02)01702-3

文献信息

• ——
  作者：E. I. Klimova、T. Klimova、M. Martinez Garcia、J. M. Martinez Mendoza、S. Hernandez Ortega、L. Ruiz Ramirez

  DOI：10.1023/a:1022460701988

  日期：——

  2-Chloro-and 2-bromo-1,1-diferrocenylcyclopropanes were synthesized as Z- and E-isomers with respect to the ferrocenyl substituent having a bisector orientation. The structure of Z-2-chloro- 1, 1 -diferrocenylcyclopropane was confirmed by X-ray diffraction analysis. Treatment of the resulting monohalides with potassium tert-butoxide in dimethyl sulfoxide afforded 3,3-diferrocenylcyclopropene in 20%' yield. The small ring in halogen- substituted diferrocenylcyclopropanes and diferrocenylcyclopropene is readily cleaved to give predominantly 3-ferrocenyl-1H-cyclopentaferrocene.