1-[(1S,2R,5R)-2,5-dimethylcyclohex-3-enyl]propan-1-one | 867265-98-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-[(1S,2R,5R)-2,5-dimethylcyclohex-3-enyl]propan-1-one
• 英文别名: 1-[(1S,2R,5R)-2,5-dimethylcyclohex-3-en-1-yl]propan-1-one
• CAS: 867265-98-3
• 化学式: C₁₁H₁₈O
• 分子量: 166.263
• InChiKey: JHSUNTFLFIJGIJ-AEJSXWLSSA-N

物化性质

• 沸点：
  226.9±29.0 °C(Predicted)
• 密度：
  0.886±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  2,4-已二烯 、 1-戊烯-3-酮 在 2,6-二叔丁基吡啶 、 chiral oxazaborolidinone 作用下， 以 二氯甲烷 为溶剂， 反应 22.0h， 生成 1-[(1S,2R,5R)-2,5-dimethylcyclohex-3-enyl]propan-1-one 、 1-[(1R,2S,5S)-2,5-dimethylcyclohex-3-enyl]propan-1-one 、 1-[(1R*,2R*,5R*)-2,5-dimethylcyclohex-3-enyl]propan-1-one
  参考文献：
  名称：

  Oxazaborolidinone-Catalyzed Enantioselective Diels−Alder Reaction of Acyclic α,β-Unsaturated Ketones

  摘要：

  [GRAPHICS]allo-Threonine-derived O-acyl-B-phenyl-oxazaborolidinones are demonstrated to be powerful and highly enantioselective Lewis acid catalysts for the Diels-Alder reaction of simple acyclic enone dienophiles, expanding the scope of ketone dienophiles and dienes. With 10 to 20 mol % of catalyst, the Diels-Alder adducts are obtained in 76-98% ee with high endo-selectivity. The catalyst exhibits high activity for the reaction with the less reactive beta-substituted dienophiles and the less reactive 1,3-cycohexadiene and 1,3-butadiene derivatives. The application of the catalysts to the Diels-Alder reaction of furan is also described.

  DOI：

  10.1021/jo702043g

文献信息

• Oxazaborolidinone-Catalyzed Enantioselective Diels−Alder Reaction of Acyclic α,β-Unsaturated Ketones
  作者：Ram Shanker Singh、Shinya Adachi、Fumi Tanaka、Toyonao Yamauchi、Chieko Inui、Toshiro Harada

  DOI：10.1021/jo702043g

  日期：2008.1.1

  [GRAPHICS]allo-Threonine-derived O-acyl-B-phenyl-oxazaborolidinones are demonstrated to be powerful and highly enantioselective Lewis acid catalysts for the Diels-Alder reaction of simple acyclic enone dienophiles, expanding the scope of ketone dienophiles and dienes. With 10 to 20 mol % of catalyst, the Diels-Alder adducts are obtained in 76-98% ee with high endo-selectivity. The catalyst exhibits high activity for the reaction with the less reactive beta-substituted dienophiles and the less reactive 1,3-cycohexadiene and 1,3-butadiene derivatives. The application of the catalysts to the Diels-Alder reaction of furan is also described.