[5]radialene | 3227-92-7

• 分子结构分类: 有机化合物 - 碳氢化合物 - 不饱和烃
• 英文名称: [5]radialene
• 英文别名: Pentaradialen；1,2,3,4,5-Pentamethylidenecyclopentane
• CAS: 3227-92-7
• 化学式: C₁₀H₁₀
• 分子量: 130.189
• InChiKey: RVBXYBDJWKWCLW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  10
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为产物：
  描述：

  在 ammonium cerium (IV) nitrate 作用下， 以 氘代丙酮 为溶剂， 反应 48.0h， 以27%的产率得到[5]radialene
  参考文献：
  名称：

  [5] Radialene

  摘要：

  The [n]radialenes are a unique family of fundamental [n]-membered carbocyclic structures with radiating alkenes, which have attracted significant synthetic and theoretical attention. Whereas [3]-, [4]-, and [6]radialenes have been prepared and studied, all efforts to synthesize the five-membered ring compound have thus far met with failure. Here we describe the first synthesis of the fundamental hydrocarbon [5]radialene, C10H10. Our approach was a departure from previous radialene syntheses in that it utilized a low-temperature decomplexation of a stable organometallic compound, rather than high-temperature elimination or rearrangement. Our strategy was guided by analysis of previous radialene syntheses, which indicated rapid decomposition in oxygen, and ab initio calculations, which revealed an extraordinary susceptibility of [5]radialene to undergo DielsAlder dimerization/polymerization. The origin of this susceptibility was traced to a small distortion energy associated with the formation of the transition structure geometry from the relaxed reactant monomers and to a narrow HOMOLUMO gap.

  DOI：

  10.1021/jacs.5b07445