1-(3-Methoxyimino-propyl)-2-oxo-cycloheptanecarboxylic acid ethyl ester | 154473-91-3

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 1-(3-Methoxyimino-propyl)-2-oxo-cycloheptanecarboxylic acid ethyl ester
• 英文别名: ethyl 1-(3-methoxyiminopropyl)-2-oxocycloheptane-1-carboxylate
• CAS: 154473-91-3
• 化学式: C₁₄H₂₃NO₄
• 分子量: 269.341
• InChiKey: LTIQICKMFZAJOS-UHFFFAOYSA-N

物化性质

• 沸点：
  370.4±52.0 °C(predicted)
• 密度：
  1.09±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.48
• 重原子数：
  19.0
• 可旋转键数：
  6.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.79
• 拓扑面积：
  64.96
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  1-(3-Methoxyimino-propyl)-2-oxo-cycloheptanecarboxylic acid ethyl ester 以 异丙醇 为溶剂， 以81%的产率得到8a-Hydroxy-1-methoxyamino-octahydro-azulene-3a-carboxylic acid ethyl ester
  参考文献：
  名称：

  Electroorganic Chemistry. 144. Electroreductive Coupling of Ketones with O-Methyl Oximes, N,N-Dimethylhydrazones, and Nitrones. A Convenient Route to Synthesis of .beta.-Amino Alcohol

  摘要：

  The intermolecular coupling of a variety of ketones with some types of O-methyl oximes took place when a mixture of both components was electrochemically reduced in i-PrOH with an Sn cathode. The product, beta-methoxyamino alcohol was easily converted to beta-amino alcohol by simple reduction. A chiral ligand effective for the enantioselective addition of diethylzinc to an aldehyde was easily obtained from the product formed by the electroreductive coupling of (-)-menthone with O-methylacetaldoxime. The intermolecular coupling of a ketone with a N,N-dimethylhydrazone or nitrone was also promoted by the electroreduction. Furthermore, the electroreductive coupling of a carbonyl group with an intramolecular O-methyl oxime moiety gave the corresponding cyclized product stereoselectively.

  DOI：

  10.1021/jo00086a023
• 作为产物：
  描述：

  2-氧代环庚烷甲酸乙酯 在 吡啶 作用下， 反应 12.0h， 生成 1-(3-Methoxyimino-propyl)-2-oxo-cycloheptanecarboxylic acid ethyl ester
  参考文献：
  名称：

  Electroorganic Chemistry. 144. Electroreductive Coupling of Ketones with O-Methyl Oximes, N,N-Dimethylhydrazones, and Nitrones. A Convenient Route to Synthesis of .beta.-Amino Alcohol

  摘要：

  The intermolecular coupling of a variety of ketones with some types of O-methyl oximes took place when a mixture of both components was electrochemically reduced in i-PrOH with an Sn cathode. The product, beta-methoxyamino alcohol was easily converted to beta-amino alcohol by simple reduction. A chiral ligand effective for the enantioselective addition of diethylzinc to an aldehyde was easily obtained from the product formed by the electroreductive coupling of (-)-menthone with O-methylacetaldoxime. The intermolecular coupling of a ketone with a N,N-dimethylhydrazone or nitrone was also promoted by the electroreduction. Furthermore, the electroreductive coupling of a carbonyl group with an intramolecular O-methyl oxime moiety gave the corresponding cyclized product stereoselectively.

  DOI：

  10.1021/jo00086a023