(1SR,7RS,9SR)-9-(3'-bromopropyl)bicyclo<5.2.0>nonan-8-one | 137629-15-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (1SR,7RS,9SR)-9-(3'-bromopropyl)bicyclo<5.2.0>nonan-8-one
• 英文别名: (1S,7R,9R)-9-(3-bromopropyl)bicyclo[5.2.0]nonan-8-one
• CAS: 137629-15-3；145554-20-7；145554-26-3
• 化学式: C₁₂H₁₉BrO
• 分子量: 259.186
• InChiKey: MNMRMGGJPLVDGT-HBNTYKKESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.92
• 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：

  (1SR,7RS,9SR)-9-(3'-bromopropyl)bicyclo<5.2.0>nonan-8-one 在 偶氮二异丁腈 、 三正丁基氢锡 作用下， 以 苯 为溶剂， 反应 2.0h， 以64%的产率得到(5aS,10aS)-Decahydro-heptalen-1-one
  参考文献：
  名称：

  Free-radical ring expansion of fused cyclobutanones: stereospecific construction of 5,7-, 6,7-, 7,7-, 8,7-, and 5,8-cis-fused bicyclic systems

  摘要：

  A new method of appending seven- and eight-membered rings to cycloalkenes is described. Treatment of selected alkene precursors with an omega-bromoalkyl ketene or a keteniminium salt leads to haloalkyl cyclobutanone formation. Tri-n-butyltin hydride promoted ring expansion then yields the annulated product. Since the initial cyclobutanone is cis fused, the final product is also produced stereospecifically with a cis ring fusion.

  DOI：

  10.1021/jo00052a034
• 作为产物：
  描述：

  环庚烯 、 5-bromo-1-(pyrrolidin-1-yl)pentan-1-one 在 2,3,5-三甲基吡啶 、 三氟甲磺酸酐 、 水 作用下， 生成 (1SR,7RS,9SR)-9-(3'-bromopropyl)bicyclo<5.2.0>nonan-8-one 、 (1SR,7RS,9RS)-9-(3'-bromopropyl)bicyclo<5.2.0>nonan-8-one
  参考文献：
  名称：

  Free-radical ring expansion of fused cyclobutanones: stereospecific construction of 5,7-, 6,7-, 7,7-, 8,7-, and 5,8-cis-fused bicyclic systems

  摘要：

  A new method of appending seven- and eight-membered rings to cycloalkenes is described. Treatment of selected alkene precursors with an omega-bromoalkyl ketene or a keteniminium salt leads to haloalkyl cyclobutanone formation. Tri-n-butyltin hydride promoted ring expansion then yields the annulated product. Since the initial cyclobutanone is cis fused, the final product is also produced stereospecifically with a cis ring fusion.

  DOI：

  10.1021/jo00052a034

文献信息

• Free radical ring expansion of fused cyclobutanones: a new ring expansion annulation stratagem
  作者：Paul Dowd、Wei Zhang

  DOI：10.1021/ja00026a037

  日期：1991.12
• Free-radical ring expansion of fused cyclobutanones: stereospecific construction of 5,7-, 6,7-, 7,7-, 8,7-, and 5,8-cis-fused bicyclic systems
  作者：Paul Dowd、Wei Zhang

  DOI：10.1021/jo00052a034

  日期：1992.12

  A new method of appending seven- and eight-membered rings to cycloalkenes is described. Treatment of selected alkene precursors with an omega-bromoalkyl ketene or a keteniminium salt leads to haloalkyl cyclobutanone formation. Tri-n-butyltin hydride promoted ring expansion then yields the annulated product. Since the initial cyclobutanone is cis fused, the final product is also produced stereospecifically with a cis ring fusion.