(1S,2S,4R)-1-(7-oxabicyclo[2.2.1]hept-2-yl)propan-1-one | 1004987-48-7

• 分子结构分类: 有机化合物 - 有机杂环化合物
• 英文名称: (1S,2S,4R)-1-(7-oxabicyclo[2.2.1]hept-2-yl)propan-1-one
• 英文别名: 1-[(1S,2S,4R)-7-oxabicyclo[2.2.1]heptan-2-yl]propan-1-one
• CAS: 1004987-48-7
• 化学式: C₉H₁₄O₂
• 分子量: 154.209
• InChiKey: COFKWVBLRFEPJV-BHNWBGBOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  11
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  呋喃 、 1-戊烯-3-酮 在 palladium on activated charcoal chiral oxazaborolidinone 、 氢气 作用下， 以 甲苯 、 正己烷 为溶剂， 反应 0.33h， 生成 (1S,2S,4R)-1-(7-oxabicyclo[2.2.1]hept-2-yl)propan-1-one 、 (1R,2S,4S)-1-(7-oxabicyclo[2.2.1]hept-2-yl)propan-1-one 、 (1S,2R,4R)-1-(7-oxabicyclo[2.2.1]hept-2-yl)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