1-ferrocenylcyclopropene | 523977-86-8

• 分子结构分类: 有机化合物 - 碳氢化合物衍生物
• 英文名称: 1-ferrocenylcyclopropene
• 英文别名: Ferrocenylcyclopropene；cyclopenta-1,3-diene;5-(cyclopropen-1-yl)cyclopenta-1,3-diene;iron(2+)
• CAS: 523977-86-8
• 化学式: C₁₃H₁₂Fe
• 分子量: 224.085
• InChiKey: CHKSFUYIRZQCMM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-ferrocenylcyclopropene 、 1,3-二苯基异苯并呋喃 以 苯 为溶剂， 以50%的产率得到exo-2-ferrocenyl-1,5-diphenyl-6,7-benzo-8-oxatricyclo[3.2.1.o(2,4)]oct-6-ene
  参考文献：
  名称：

  1-Ferrocenylcyclopropene and 1-ferrocenylcyclopropyl cation

  摘要：

  Dehydrobromination of cis and trans isomers of 1-bromo-2-ferrocenylcyclopropanes affords 1-ferrocenylcyclopropene. Its protonation with HBF4 results in 1-ferrocenylcyclopropylium tetrafluoroborate, which alkylates N,N-dimethylaniline in para position to yield 1-(p-dimethylaminophenyl)-l-ferrocenyleyclopropane. 1-Ferrocenylcyclopropene reacts with 1,3-diphenylisobenzofuran to give the classical [4+2]-cycloaddition product. Its structure as exo-2-ferrocenyl-1,5-diphenyl-6,7-benzo-8-oxatricyclo[3.2.1.0(2,4)] oct-6-ene was established based on the data from X-ray diffraction analysis. (C) 2002 Elsevier Science B.V. All rights reserved.

  DOI：

  10.1016/s0022-328x(02)02037-5
• 作为产物：
  描述：

  trans-1-bromo-2-ferrocenylcyclopropane 在 potassium tert-butoxide 作用下， 以 二甲基亚砜 为溶剂， 以42%的产率得到1-ferrocenylcyclopropene
  参考文献：
  名称：

  1-Ferrocenylcyclopropene and 1-ferrocenylcyclopropyl cation

  摘要：

  Dehydrobromination of cis and trans isomers of 1-bromo-2-ferrocenylcyclopropanes affords 1-ferrocenylcyclopropene. Its protonation with HBF4 results in 1-ferrocenylcyclopropylium tetrafluoroborate, which alkylates N,N-dimethylaniline in para position to yield 1-(p-dimethylaminophenyl)-l-ferrocenyleyclopropane. 1-Ferrocenylcyclopropene reacts with 1,3-diphenylisobenzofuran to give the classical [4+2]-cycloaddition product. Its structure as exo-2-ferrocenyl-1,5-diphenyl-6,7-benzo-8-oxatricyclo[3.2.1.0(2,4)] oct-6-ene was established based on the data from X-ray diffraction analysis. (C) 2002 Elsevier Science B.V. All rights reserved.

  DOI：

  10.1016/s0022-328x(02)02037-5