7-endo-(3-bromopropyl)bicyclo<3.2.0>hept-2-en-6-one

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 7-endo-(3-bromopropyl)bicyclo<3.2.0>hept-2-en-6-one
• 英文别名: (1S,5S,7R)-7-(3-bromopropyl)bicyclo[3.2.0]hept-2-en-6-one
• 化学式: C₁₀H₁₃BrO
• 分子量: 229.117
• InChiKey: AMYHJMIXRAPEQC-HRDYMLBCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  7-endo-(3-bromopropyl)bicyclo<3.2.0>hept-2-en-6-one 在 silver tetrafluoroborate 、 N-溴代乙酰胺 作用下， 以 水 、 丙酮 为溶剂， 反应 16.0h， 生成 (1R,3S,5R,7R)-2-Bromo-3-hydroxy-7-(3-methoxy-propyl)-bicyclo[3.2.0]heptan-6-one
  参考文献：
  名称：

  Synthesis of (+)-brefeldin-A

  摘要：

  Two routes to (+)-brefeldin A have been investigated. In one the bicyclic ketone 2 was transformed into the hydroxy lactone 7. Subsequent reduction, opening of the heterocyclic ring and epimerization furnished the aldehyde 13. Further steps towards the natural product from this late stage intermediate 13 were not investigated. in the second route, the readily available hydroxy lactone 17 was converted into the enone 22. Conjugate addition of the requisite cuprate reagent to this enone afforded the 3,4-disubstituted cyclopentanone 24 which was converted into brefeldin-A 29 in five steps.

  DOI：

  10.1039/p19940003431
• 作为产物：
  描述：

  7-(3-bromopropyl)-7-chlorobicyclo<3.2.0>hept-2-en-6-one 在 氯化铵 、 锌 作用下， 以 甲醇 为溶剂， 反应 5.5h， 以77%的产率得到7-endo-(3-bromopropyl)bicyclo<3.2.0>hept-2-en-6-one
  参考文献：
  名称：

  Synthesis of (+)-brefeldin-A

  摘要：

  Two routes to (+)-brefeldin A have been investigated. In one the bicyclic ketone 2 was transformed into the hydroxy lactone 7. Subsequent reduction, opening of the heterocyclic ring and epimerization furnished the aldehyde 13. Further steps towards the natural product from this late stage intermediate 13 were not investigated. in the second route, the readily available hydroxy lactone 17 was converted into the enone 22. Conjugate addition of the requisite cuprate reagent to this enone afforded the 3,4-disubstituted cyclopentanone 24 which was converted into brefeldin-A 29 in five steps.

  DOI：

  10.1039/p19940003431

文献信息

• Synthesis of (+)-brefeldin-A
  作者：Andrew J. Carnell、Guy Casy、Gilles Gorins、Arefeh Kompany-Saeid、Ray McCague、Horacio F. Olivo、Stanley M. Roberts、Andrew J. Willetts

  DOI：10.1039/p19940003431

  日期：——

  Two routes to (+)-brefeldin A have been investigated. In one the bicyclic ketone 2 was transformed into the hydroxy lactone 7. Subsequent reduction, opening of the heterocyclic ring and epimerization furnished the aldehyde 13. Further steps towards the natural product from this late stage intermediate 13 were not investigated. in the second route, the readily available hydroxy lactone 17 was converted into the enone 22. Conjugate addition of the requisite cuprate reagent to this enone afforded the 3,4-disubstituted cyclopentanone 24 which was converted into brefeldin-A 29 in five steps.