1-[(1S,2R,3R,4R)-3-(4-chlorophenyl)bicyclo[2.2.1]hept-5-en-2-yl]ethanone | 1004987-39-6

• 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: 1-[(1S,2R,3R,4R)-3-(4-chlorophenyl)bicyclo[2.2.1]hept-5-en-2-yl]ethanone
• 英文别名: 1-[(1S,2R,3R,4R)-3-(4-chlorophenyl)-2-bicyclo[2.2.1]hept-5-enyl]ethanone
• CAS: 1004987-39-6
• 化学式: C₁₅H₁₅ClO
• 分子量: 246.737
• InChiKey: YRGIEYKCTXRDGM-AYRXBEOTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.4
• 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：

  (3E)-4-(4-chlorophenyl)-3-buten-2-one 、 环戊二烯 在 2,6-二叔丁基吡啶 、 chiral oxazaborolidinone 作用下， 以 二氯甲烷 为溶剂， 反应 72.0h， 生成 1-[(1S,2R,3R,4R)-3-(4-chlorophenyl)bicyclo[2.2.1]hept-5-en-2-yl]ethanone 、 1-[(1R,2S,3S,4S)-3-(4-chlorophenyl)bicyclo[2.2.1]hept-5-en-2-yl]ethanone
  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.