(+)-(2S,3R)-2-benzyl-4,4-dichloro-3-[(1R)-1-(2,4,6-triisopropylphenyl)ethoxy]cyclobutanone | 210964-88-8

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: (+)-(2S,3R)-2-benzyl-4,4-dichloro-3-[(1R)-1-(2,4,6-triisopropylphenyl)ethoxy]cyclobutanone
• 英文别名: (3R,4S)-4-benzyl-2,2-dichloro-3-[(1R)-1-[2,4,6-tri(propan-2-yl)phenyl]ethoxy]cyclobutan-1-one
• CAS: 210964-88-8
• 化学式: C₂₈H₃₆Cl₂O₂
• 分子量: 475.499
• InChiKey: KPAAOWMQYRUUOY-RMQVNJIYSA-N

物化性质

• 熔点：
  115-116 °C(Solvent: Acetone)
• 沸点：
  526.554±50.00 °C(Press: 760.00 Torr)(predicted)
• 密度：
  1.132±0.10 g/cm3(Temp: 25 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  8.1
• 重原子数：
  32
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (+)-(2S,3R)-2-benzyl-4,4-dichloro-3-[(1R)-1-(2,4,6-triisopropylphenyl)ethoxy]cyclobutanone 在 2,4,6-三甲基苯磺酰羟胺 作用下， 以 二氯甲烷 为溶剂， 反应 0.67h， 生成 (4R,5S)-5-benzyl-3,3-dichloro-4-[(1R)-1-(2,4,6-triisopropylphenyl)ethoxy]-2-pyrrolidinone
  参考文献：
  名称：

  Practical Asymmetric Approach to Pyrrolidinones:  Efficient Synthesis of (+)-Preussin and (−)-AHPPA

  摘要：

  A novel, dichloroketene-chiral enol ether cycloaddition-based synthesis of enantiopure (+)-preussin and (-)-AHPPA has been realized. The efficient, highly stereoselective approach, which involves a Beckmann ring expansion reaction to access the key pyrrolidinone, proceeds in ca. 16% overall yield for each of the compounds.

  DOI：

  10.1021/jo9801162
• 作为产物：
  描述：

  2-{(1R)-1-[(3-phenyl-1-propynyl)oxy]ethyl}-1,3,5-triisopropylbenzene 在 palladium on barium sulfate 氢气 、 铜 、 锌 作用下， 以 吡啶 、 乙醚 为溶剂， 反应 7.5h， 生成 (+)-(2S,3R)-2-benzyl-4,4-dichloro-3-[(1R)-1-(2,4,6-triisopropylphenyl)ethoxy]cyclobutanone
  参考文献：
  名称：

  Practical Asymmetric Approach to Pyrrolidinones:  Efficient Synthesis of (+)-Preussin and (−)-AHPPA

  摘要：

  A novel, dichloroketene-chiral enol ether cycloaddition-based synthesis of enantiopure (+)-preussin and (-)-AHPPA has been realized. The efficient, highly stereoselective approach, which involves a Beckmann ring expansion reaction to access the key pyrrolidinone, proceeds in ca. 16% overall yield for each of the compounds.

  DOI：

  10.1021/jo9801162

文献信息

• Practical Asymmetric Approach to Pyrrolidinones:  Efficient Synthesis of (+)-Preussin and (−)-AHPPA
  作者：Alice Kanazawa、Sandra Gillet、Philippe Delair、Andrew E. Greene

  DOI：10.1021/jo9801162

  日期：1998.7.1

  A novel, dichloroketene-chiral enol ether cycloaddition-based synthesis of enantiopure (+)-preussin and (-)-AHPPA has been realized. The efficient, highly stereoselective approach, which involves a Beckmann ring expansion reaction to access the key pyrrolidinone, proceeds in ca. 16% overall yield for each of the compounds.