(2S)-2-(2-oxopropyl)-2-prop-2-enyl-3,4-dihydronaphthalen-1-one | 1026243-42-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 四氢化萘
• 英文名称: (2S)-2-(2-oxopropyl)-2-prop-2-enyl-3,4-dihydronaphthalen-1-one
• CAS: 1026243-42-4
• 化学式: C₁₆H₁₈O₂
• 分子量: 242.318
• InChiKey: DPOSVPLPXVXLEJ-MRXNPFEDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 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-(2-oxopropyl)-2-prop-2-enyl-3,4-dihydronaphthalen-1-one 在 sodium ethanolate 作用下， 以 乙醇 为溶剂， 反应 24.0h， 生成 (3aS)-3a-prop-2-enyl-4,5-dihydro-3H-cyclopenta[a]naphthalen-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：

  1-溴-2-(2-碘乙基)苯 在 叔丁基锂 、 四丁基磷酸氢铵 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 为溶剂， 反应 20.0h， 生成 (2S)-2-(2-oxopropyl)-2-prop-2-enyl-3,4-dihydronaphthalen-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.