(R)-2-Ethyl-2-(2-oxo-propyl)-cyclohexanone | 139125-57-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (R)-2-Ethyl-2-(2-oxo-propyl)-cyclohexanone
• 英文别名: (2R)-2-ethyl-2-(2-oxopropyl)cyclohexan-1-one
• CAS: 139125-57-8
• 化学式: C₁₁H₁₈O₂
• 分子量: 182.263
• InChiKey: KDPSIANEWCSARC-LLVKDONJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  34.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (R)-2-Ethyl-2-(2-oxo-propyl)-cyclohexanone 在 氢氧化钾 作用下， 以 乙醇 为溶剂， 反应 16.0h， 生成 (R)-7a-Ethyl-1,4,5,6,7,7a-hexahydro-inden-2-one
  参考文献：
  名称：

  Synthesis of enantiomerically pure hydrinden-2-ones and benz[e]inden-2-ones via asymmetric alkylations of chiral bicyclic lactams

  摘要：

  A route to the titled compounds in >99 % ee was achieved from sequential diastereoselective alkylations of chiral, nonracemic bicyclic lactams 6 and 15. An intramolecular addition of the organolithium species derived from 17a-c and 28a-d gave, after hydrolysis, diketones 25a-c and 30a-d, which were cyclized to the titled compounds 4a-c and 31a-d. As an example of the versatility of this method, the ABC ring system of the triterpene stelliferin A, isolated from marine organisms, was prepared in high enantiomeric excess.

  DOI：

  10.1021/jo00078a032
• 作为产物：
  描述：

  (3S,6R,7aR)-3-tert-Butyl-6-ethyl-6-(4-hydroxy-butyl)-7a-methyl-tetrahydro-pyrrolo[2,1-b]oxazol-5-one 在 N-溴代丁二酰亚胺(NBS) 、 水 、 叔丁基锂 、 potassium hydride 、 四丁基磷酸氢铵 、 三苯基膦 作用下， 以 二氯甲烷 为溶剂， 反应 13.75h， 生成 (R)-2-Ethyl-2-(2-oxo-propyl)-cyclohexanone
  参考文献：
  名称：

  Synthesis of enantiomerically pure hydrinden-2-ones and benz[e]inden-2-ones via asymmetric alkylations of chiral bicyclic lactams

  摘要：

  A route to the titled compounds in >99 % ee was achieved from sequential diastereoselective alkylations of chiral, nonracemic bicyclic lactams 6 and 15. An intramolecular addition of the organolithium species derived from 17a-c and 28a-d gave, after hydrolysis, diketones 25a-c and 30a-d, which were cyclized to the titled compounds 4a-c and 31a-d. As an example of the versatility of this method, the ABC ring system of the triterpene stelliferin A, isolated from marine organisms, was prepared in high enantiomeric excess.

  DOI：

  10.1021/jo00078a032