(1R,4S,6S)-6-acetoxybicyclo[2.2.2]octan-2-one | 129025-71-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (1R,4S,6S)-6-acetoxybicyclo[2.2.2]octan-2-one
• 英文别名: [(1R,2S,4S)-6-oxo-2-bicyclo[2.2.2]octanyl] acetate
• CAS: 129025-71-4
• 化学式: C₁₀H₁₄O₃
• 分子量: 182.219
• InChiKey: YCRGHUPHGIYXNP-WEDXCCLWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (1R,4S,6S)-6-acetoxybicyclo[2.2.2]octan-2-one 在 三乙胺 、 lithium bromide 、 zinc(II) chloride 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 为溶剂， 反应 49.0h， 生成 Acetic acid (1R,2S,4S)-5-[1-chloro-eth-(E)-ylidene]-6-oxo-bicyclo[2.2.2]oct-2-yl ester
  参考文献：
  名称：

  Neighboring Group Participation in a Regio- and Stereoselective Chlorination of a Bicyclo[2.2.2]octanone

  摘要：

  The zinc chloride-mediated acetylation of the optically active silyl enol ether 2a gave the beta-diketone 3a (48%) together with the regio- and stereoselectively chlorinated compound 4 (27%). The yield of 4 increased to 70% by starting from the O-acetyl derivative 2c. The chlorination most likely occurs via neighboring group participation by the endo acetoxy group.

  DOI：

  10.1021/jo9607370
• 作为产物：
  描述：

  (1R,4S,6S)-6-<(tert-butyldimethylsilyl)oxy>bicyclo<2.2.2>octan-2-one 在 zinc(II) chloride 、 lithium diisopropyl amide 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 生成 (1R,4S,6S)-6-acetoxybicyclo[2.2.2]octan-2-one
  参考文献：
  名称：

  Neighboring Group Participation in a Regio- and Stereoselective Chlorination of a Bicyclo[2.2.2]octanone

  摘要：

  The zinc chloride-mediated acetylation of the optically active silyl enol ether 2a gave the beta-diketone 3a (48%) together with the regio- and stereoselectively chlorinated compound 4 (27%). The yield of 4 increased to 70% by starting from the O-acetyl derivative 2c. The chlorination most likely occurs via neighboring group participation by the endo acetoxy group.

  DOI：

  10.1021/jo9607370