(1aR,3aS,7bR)-3a,5,5'-Tribromo-1a,2,3,3a,5,6,7,7b-octahydro-4H-cyclobutazulen-4-one

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (1aR,3aS,7bR)-3a,5,5'-Tribromo-1a,2,3,3a,5,6,7,7b-octahydro-4H-cyclobutazulen-4-one
• 英文别名: (1aR,3aS,7bR)-3a,5,5-tribromo-1a,2,3,3a,5,6,7,7b-octahydro-4H-cyclobuta[cd]azulen-4-one；(3R,6S,11R)-6,8,8-tribromotricyclo[4.4.1.03,11]undec-1-en-7-one
• 化学式: C₁₁H₁₁Br₃O
• 分子量: 398.92
• InChiKey: WXSCXUGUOSGHMS-YNEQXMIYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  15
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  (1aR,3aR,5R,7bS)-5-Bromo-1a,2,3,3a,5,6,7,7b-octahydro-4H-cyclobutazulen-4-one 在 三甲基氯硅烷 、 sodium iodide 作用下， 以 乙腈 为溶剂， 反应 2.0h， 生成 (1aR,3aS,7bR)-3a,5,5'-Tribromo-1a,2,3,3a,5,6,7,7b-octahydro-4H-cyclobutazulen-4-one
  参考文献：
  名称：

  In Quest of Tricyclo[4.4.1.04,11]undeca-1,3,5,7,9-pentaene, a Highly Strained, Cyclic 10.pi.-Electron, Polyunsaturated Hydrocarbon. Synthesis of a Methoxyl-Substituted Dihydro Derivative

  摘要：

  Ketone 9, which can be rapidly prepared from 2-cyclohexenone in three steps, has been examined for its suitability as a template for the generation of the title hydrocarbon 5. The stepwise regiocontrolled introduction of two bromine atoms has resulted in the acquisition of 17, 22, or 23 depending upon conditions. The tribromo enone 18 has also been generated; although the more pivotal intermediate 24 has not been seen. Dehydrobromination experiments performed on these halogenated products have given rise to dienone 15 and trienone 19, both of which have proven to be rather sensitive compounds, The O-methylation of 19 could be accomplished to give 26, the maximally unsaturated member of this series generated to date. This tetraene polymerizes rapidly in its pure oily state or in solution when exposed to air.

  DOI：

  10.1021/jo00104a029

文献信息

• Branan Bruce M., Paquette Leo A., J. Org. Chem, 59 (1994) N 25, S 7709-7713
  作者：Branan Bruce M., Paquette Leo A.

  DOI：——

  日期：——
• In Quest of Tricyclo[4.4.1.04,11]undeca-1,3,5,7,9-pentaene, a Highly Strained, Cyclic 10.pi.-Electron, Polyunsaturated Hydrocarbon. Synthesis of a Methoxyl-Substituted Dihydro Derivative
  作者：Bruce M. Branan、Leo A. Paquette

  DOI：10.1021/jo00104a029

  日期：1994.12

  Ketone 9, which can be rapidly prepared from 2-cyclohexenone in three steps, has been examined for its suitability as a template for the generation of the title hydrocarbon 5. The stepwise regiocontrolled introduction of two bromine atoms has resulted in the acquisition of 17, 22, or 23 depending upon conditions. The tribromo enone 18 has also been generated; although the more pivotal intermediate 24 has not been seen. Dehydrobromination experiments performed on these halogenated products have given rise to dienone 15 and trienone 19, both of which have proven to be rather sensitive compounds, The O-methylation of 19 could be accomplished to give 26, the maximally unsaturated member of this series generated to date. This tetraene polymerizes rapidly in its pure oily state or in solution when exposed to air.