(2S)-2-benzyl-2-(2-oxopropyl)cyclohexan-1-one | 139125-55-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (2S)-2-benzyl-2-(2-oxopropyl)cyclohexan-1-one
• CAS: 139125-55-6
• 化学式: C₁₆H₂₀O₂
• 分子量: 244.334
• InChiKey: CEMYGOBKBQNKGL-MRXNPFEDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 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：

  (2S)-2-benzyl-2-(2-oxopropyl)cyclohexan-1-one 在 氢氧化钾 作用下， 以 乙醇 为溶剂， 反应 16.0h， 生成 (7aS)-7a-benzyl-4,5,6,7-tetrahydro-1H-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：

  (3R-顺)-(-)-3-异丙基-7α-甲基四氢吡咯并-[2,1-b]噁唑-5(6H)-酮 在 sodium hydroxide 、 N-溴代丁二酰亚胺(NBS) 、 9-borabicyclo[3.3.1]nonane dimer 、 水 、 双氧水 、 叔丁基锂 、 potassium hydride 、 四丁基磷酸氢铵 、 三苯基膦 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 33.25h， 生成 (2S)-2-benzyl-2-(2-oxopropyl)cyclohexan-1-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

文献信息

• Synthesis of enantiomerically pure hydrinden-2-ones and benz[e]inden-2-ones via asymmetric alkylations of chiral bicyclic lactams
  作者：Lawrence Snyder、A. I. Meyers

  DOI：10.1021/jo00078a032

  日期：1993.12

  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.