1-[(1S,2R,3R,4R)-3-(4-methoxyphenyl)-2-bicyclo[2.2.1]hept-5-enyl]ethanone

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 1-[(1S,2R,3R,4R)-3-(4-methoxyphenyl)-2-bicyclo[2.2.1]hept-5-enyl]ethanone
• 化学式: C₁₆H₁₈O₂
• 分子量: 242.318
• InChiKey: PCIXRONFFXSOFL-OCVGTWLNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.44
• 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：

  1-(4-methoxyphenyl)-2-butyn-1-ol 在 [ReOCl3(OPPh3)(SMe2)] 、 三氟化硼乙醚 作用下， 以 乙二醇二甲醚 、 乙醚 为溶剂， 反应 16.0h， 生成 1-[(1S,2R,3R,4R)-3-(4-methoxyphenyl)-2-bicyclo[2.2.1]hept-5-enyl]ethanone
  参考文献：
  名称：

  基于重新催化的Meyer-Schuster重排合成共轭烯酮的单锅连续反应

  摘要：

  单锅反应中的重催化：一种原子经济的单锅策略，涉及炔烃去质子化和随后and（V）催化的炔诺醇的Meyer-Schuster重排，以提供高产率的α，ß-不饱和烯酮开发（请参阅计划）。随后进行的烯酮的原位氢化物还原或Diels-Alder反应可提供高至高总收率的产品。

  DOI：

  10.1002/chem.201201639

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.
• One-Pot Consecutive Reactions Based on the Synthesis of Conjugated Enones by the Re-Catalysed Meyer-Schuster Rearrangement
  作者：Elio Mattia、Alessio Porta、Valentina Merlini、Giuseppe Zanoni、Giovanni Vidari

  DOI：10.1002/chem.201201639

  日期：2012.9.17

  Re catalysis in one‐pot reactions: An atom‐economical, one‐pot strategy that involves alkyne deprotonation and a subsequent rhenium(V)‐catalysed Meyer–Schuster rearrangement of the alkynol to provide α,ß‐unsaturated enones in high yield has been developed (see scheme). Subsequent in situ hydride reduction or Diels–Alder reaction of the enones provided products in good‐to‐high overall yields.

  单锅反应中的重催化：一种原子经济的单锅策略，涉及炔烃去质子化和随后and（V）催化的炔诺醇的Meyer-Schuster重排，以提供高产率的α，ß-不饱和烯酮开发（请参阅计划）。随后进行的烯酮的原位氢化物还原或Diels-Alder反应可提供高至高总收率的产品。