2,3-bis(bromomethyl)bicyclo<2.2.2>octa-2,5-diene | 173372-89-9

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 有机溴化物
• 英文名称: 2,3-bis(bromomethyl)bicyclo<2.2.2>octa-2,5-diene
• 英文别名: 2,3-bis(bromomethyl)bicyclo[2.2.2]octa-2,5-diene
• CAS: 173372-89-9
• 化学式: C₁₀H₁₂Br₂
• 分子量: 292.013
• InChiKey: RYJLGEDSYAMSDT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.67
• 重原子数：
  12.0
• 可旋转键数：
  2.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  0.0
• 氢给体数：
  0.0
• 氢受体数：
  0.0

反应信息

• 作为反应物：
  描述：

  2,3-bis(bromomethyl)bicyclo<2.2.2>octa-2,5-diene 在 potassium tert-butylate 作用下， 以 乙醚 、 氘代氯仿 为溶剂， 反应 0.5h， 生成 1,4-dihydro-1,4-ethano-6,7-bis(methoxycarbonyl)naphthalene
  参考文献：
  名称：

  Unexpected Formation of Dienes in the Diels−Alder Reaction of Exocyclic 1-Bromobutadienes of Polycyclic Hydrocarbons

  摘要：

  Polycyclic dienes having an exocyclic 1-bromobutadiene moiety react with dienophiles and fullerene-C-60 to afford exclusively dienes via a cycloaddition-elimination mechanism. Neither the primary adducts nor the double addition products derived from a second cycloaddition of the dienophile to the diene could be detected. In one case only, i.e. with 4-phenyl-1,2,4-triazoline-3,5-dione, was the double addition product formed. Contrary to expectations, X-ray diffractometric analysis shows that this adduct is formed following a contrasteric approach.

  DOI：

  10.1021/jo951434t
• 作为产物：
  描述：

  dimethyl bicyclo[2.2.2]octa-2,5-diene-2,3-dicarboxylate 在 吡啶 、 三溴化磷 、 二异丁基氢化铝 作用下， 以 乙醚 、 环己烷 为溶剂， 反应 38.0h， 生成 2,3-bis(bromomethyl)bicyclo<2.2.2>octa-2,5-diene
  参考文献：
  名称：

  Unexpected Formation of Dienes in the Diels−Alder Reaction of Exocyclic 1-Bromobutadienes of Polycyclic Hydrocarbons

  摘要：

  Polycyclic dienes having an exocyclic 1-bromobutadiene moiety react with dienophiles and fullerene-C-60 to afford exclusively dienes via a cycloaddition-elimination mechanism. Neither the primary adducts nor the double addition products derived from a second cycloaddition of the dienophile to the diene could be detected. In one case only, i.e. with 4-phenyl-1,2,4-triazoline-3,5-dione, was the double addition product formed. Contrary to expectations, X-ray diffractometric analysis shows that this adduct is formed following a contrasteric approach.

  DOI：

  10.1021/jo951434t