2-bromopropyl diazomethyl ketone | 1584693-16-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-bromopropyl diazomethyl ketone
• 英文别名: 4-Bromo-1-diazopentan-2-one
• CAS: 1584693-16-2
• 化学式: C₅H₇BrN₂O
• 分子量: 191.027
• InChiKey: IAVPNGUUILYEPV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  9
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  19.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-bromopropyl diazomethyl ketone 、 3-(tert-butyldiphenylsilyl)propene 在 dirhodium tetraacetate 作用下， 以 氯仿 为溶剂， 反应 18.0h， 生成 2-(tert-butyldiphenylsilylmethyl)cyclopropyl 2-bromopropyl ketone
  参考文献：
  名称：

  Allylsilane-interrupted homo-Nazarov cyclization and synthesis of bicyclo[3.2.1]octan-8-ones

  摘要：

  The combination of homo-Nazarov cyclization of 2-(tert-butyldiphenylsilylmethyl)cyclopropyl vinyl ketone leading to oxyallyl cation and its subsequent [3+2] capture by allylsilane has been demonstrated as an useful strategy for the construction of functionalized bicyclo[3.2.1]octan-8-ones. The [3+2] capture proceeds exclusively in the exo mode to make the overall reaction diastereoselective. The less substituted end of the oxyallyl cation was found to react nearly two times faster than the more substituted end. (c) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2014.02.018
• 作为产物：
  描述：

  重氮甲烷 、 β-bromobutyryl chloride 以 乙醚 为溶剂， 反应 0.25h， 以3.1 g的产率得到2-bromopropyl diazomethyl ketone
  参考文献：
  名称：

  Allylsilane-interrupted homo-Nazarov cyclization and synthesis of bicyclo[3.2.1]octan-8-ones

  摘要：

  The combination of homo-Nazarov cyclization of 2-(tert-butyldiphenylsilylmethyl)cyclopropyl vinyl ketone leading to oxyallyl cation and its subsequent [3+2] capture by allylsilane has been demonstrated as an useful strategy for the construction of functionalized bicyclo[3.2.1]octan-8-ones. The [3+2] capture proceeds exclusively in the exo mode to make the overall reaction diastereoselective. The less substituted end of the oxyallyl cation was found to react nearly two times faster than the more substituted end. (c) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2014.02.018