2-Acetyl-5-[(E)-methoxyimino]-2-methyl-pentanoic acid ethyl ester | 154473-92-4

• 分子结构分类: 有机化合物 - 脂质和类脂质分子
• 英文名称: 2-Acetyl-5-[(E)-methoxyimino]-2-methyl-pentanoic acid ethyl ester
• 英文别名: ethyl 2-acetyl-5-methoxyimino-2-methylpentanoate
• CAS: 154473-92-4
• 化学式: C₁₁H₁₉NO₄
• 分子量: 229.276
• InChiKey: VCPIAKNHNFCOKU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.56
• 重原子数：
  16.0
• 可旋转键数：
  7.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.73
• 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：

  2-Acetyl-5-[(E)-methoxyimino]-2-methyl-pentanoic acid ethyl ester 以 异丙醇 为溶剂， 生成 (1S,2S,3S)-2-Hydroxy-3-methoxyamino-1,2-dimethyl-cyclopentanecarboxylic acid ethyl ester 、 (1S,2R,3R)-2-Hydroxy-3-methoxyamino-1,2-dimethyl-cyclopentanecarboxylic acid ethyl ester 、 (1S,2R,3S)-2-Hydroxy-3-methoxyamino-1,2-dimethyl-cyclopentanecarboxylic 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-甲基乙酰乙酸乙酯 、 alkaline earth salt of/the/ methylsulfuric acid 在 吡啶 作用下， 反应 12.0h， 生成 2-Acetyl-5-[(E)-methoxyimino]-2-methyl-pentanoic 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