2,2,5-Tribromo-cyclopentanone | 932-06-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,2,5-Tribromo-cyclopentanone
• CAS: 932-06-9
• 化学式: C₅H₅Br₃O
• 分子量: 320.806
• InChiKey: OIWXUOIPYFMRJE-UHFFFAOYSA-N

物化性质

• 沸点：
  270.6±40.0 °C(Predicted)
• 密度：
  2.531±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  9.0
• 可旋转键数：
  0.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  17.07
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  2,2,5-Tribromo-cyclopentanone 在 水 作用下， 反应 48.0h， 生成 3-bromo-2-hydroxycyclopent-2-en-1-one
  参考文献：
  名称：

  Total Synthesis of Dimethyl Glolosiphone Aviaα-Carbonyl Radical Spiro-Cyclization

  摘要：

  AbstractA general approach toward spiro[4.4]nonane structure based on the α‐carbonyl radical cyclization has been developed. Efficient total synthesis of dimethyl gloiosiphone A (2) was achieved. Thus, alkylation of the anion of dimethylhydrazone of cyclopentanone with 5‐iodopent‐1‐yne followed by hydrolysis gave ketone 4. Iodination of 4 via its TMS‐enol ether yielded iodo ketone 7. Radical spiro‐cyclization of 7 gave spiro ketone 10. Iodination of 10 afford iodo spiro ketone 23. Oxidation and iodination of 23 gave compound 24. Methylation of 24 furnished methoxy iodo enone 25. Substitution of iodide in 25 with methoxide produced dimethoxy enone 26. Allylic oxidation of 26 gave diketone 27. Treatment of 27 with OsO4 and N‐methylmorpholine N‐oxide gave dihydroxy ketone 28. Methylation of the primary alcohol group in 28 afforded dimethyl gloiosiphone A (2).

  DOI：

  10.1002/jccs.199900064
• 作为产物：
  描述：

  环戊酮 在 氢溴酸 、 溴 作用下， 反应 8.0h， 生成 2,2,5-Tribromo-cyclopentanone
  参考文献：
  名称：

  Total Synthesis of Dimethyl Glolosiphone Aviaα-Carbonyl Radical Spiro-Cyclization

  摘要：

  AbstractA general approach toward spiro[4.4]nonane structure based on the α‐carbonyl radical cyclization has been developed. Efficient total synthesis of dimethyl gloiosiphone A (2) was achieved. Thus, alkylation of the anion of dimethylhydrazone of cyclopentanone with 5‐iodopent‐1‐yne followed by hydrolysis gave ketone 4. Iodination of 4 via its TMS‐enol ether yielded iodo ketone 7. Radical spiro‐cyclization of 7 gave spiro ketone 10. Iodination of 10 afford iodo spiro ketone 23. Oxidation and iodination of 23 gave compound 24. Methylation of 24 furnished methoxy iodo enone 25. Substitution of iodide in 25 with methoxide produced dimethoxy enone 26. Allylic oxidation of 26 gave diketone 27. Treatment of 27 with OsO4 and N‐methylmorpholine N‐oxide gave dihydroxy ketone 28. Methylation of the primary alcohol group in 28 afforded dimethyl gloiosiphone A (2).

  DOI：

  10.1002/jccs.199900064