(1S,2S,4R)-1-(7-oxabicyclo[2.2.1]hept-5-en-2-yl)ethanone | 1004987-53-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧唑烯
• 英文名称: (1S,2S,4R)-1-(7-oxabicyclo[2.2.1]hept-5-en-2-yl)ethanone
• 英文别名: 1-[(1S,2S,4R)-7-oxabicyclo[2.2.1]heptan-2-yl]ethanone
• CAS: 1004987-53-4
• 化学式: C₈H₁₂O₂
• 分子量: 140.182
• InChiKey: AJENGVZEIVIXKF-PRJMDXOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  10
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.88
• 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：

  丁烯酮 、 呋喃 在 palladium on activated charcoal chiral oxazaborolidinone 、 氢气 作用下， 以 甲苯 为溶剂， 反应 0.3h， 生成 endo-2-acetyl-7-oxabicyclo<2.2.1>heptane 、 (1S,2S,4R)-1-(7-oxabicyclo[2.2.1]hept-5-en-2-yl)ethanone 、 exo-2-acetyl-7-oxabicyclo<2.2.1>heptane
  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.