(1RS,5RS,7RS)-7-chloro-1-hydroxy-7-methylbicyclo[3.2.0]heptan-6-one | 73199-37-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (1RS,5RS,7RS)-7-chloro-1-hydroxy-7-methylbicyclo[3.2.0]heptan-6-one
• 英文别名: 7-chloro-1-hydroxy-7endo-methylbicyclo<3.2.0>heptan-6-one
• CAS: 73199-37-8
• 化学式: C₈H₁₁ClO₂
• 分子量: 174.627
• InChiKey: AFQQQWJBIBAFRO-NJUXHZRNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  11.0
• 可旋转键数：
  0.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  37.3
• 氢给体数：
  1.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  (1RS,5RS,7RS)-7-chloro-1-hydroxy-7-methylbicyclo[3.2.0]heptan-6-one 在 水 、 锌 作用下， 以 异丙醇 为溶剂， 反应 49.0h， 以18 mg的产率得到(1SR,5RS,7SR)-1-hydroxy-7-methylbicyclo[3.2.0]heptan-6-one
  参考文献：
  名称：

  Synthesis of 2-Substituted 1,3-Cycloheptanedione via a Lewis Acid Mediated Ring Expansion Reaction

  摘要：

  We have established a new route to provide 2-substituted 1,3-cycloheptanediones via a Lewis acid mediated ring expansion reaction of cyclobutanones as the key step. The ring expansion reactions were mediated by a series of Lewis acids. Among the used Lewis acids, ZnI2 was the most practical mediator. This route has succeeded in providing the title compounds even on a multi-gram scale. During the research, the Baeyer-Villiger oxidation of the cyclobutanones to obtain the new bicyclic lactones was also examined. The regioselective oxidation was observed in the case of chlorinated cyclobutanones.

  DOI：

  10.3987/com-13-s(s)55
• 作为产物：
  描述：

  7-chloro-7-methyl-1-(trimethylsiloxy)bicyclo<3.2.0>heptan-6-one 在 盐酸 作用下， 以 甲醇 为溶剂， 生成 (1RS,5RS,7RS)-7-chloro-1-hydroxy-7-methylbicyclo[3.2.0]heptan-6-one 、 7-chloro-1-hydroxy-7exo-methylbicyclo<3.2.0>heptan-6-one
  参考文献：
  名称：

  Halogenated ketenes. 33. Cycloaddition of ketenes and trimethylsilyl enol ethers

  摘要：

  DOI：

  10.1021/jo01298a064