3-(1-Methyl-2-oxo-cyclohexyl)-propionaldehyde | 52815-09-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-(1-Methyl-2-oxo-cyclohexyl)-propionaldehyde
• 英文别名: 1-Methyl-2-oxocyclohexanepropanal；3-(1-methyl-2-oxocyclohexyl)propanal
• CAS: 52815-09-5
• 化学式: C₁₀H₁₆O₂
• 分子量: 168.236
• InChiKey: NXYMJFSUTBMLAB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  34.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-(1-Methyl-2-oxo-cyclohexyl)-propionaldehyde 在 吡啶 作用下， 以 异丙醇 为溶剂， 反应 12.0h， 生成 (3R,3aR,7aS)-3-Methoxyamino-7a-methyl-octahydro-inden-3a-ol
  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

文献信息

• 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
  作者：Tatsuya Shono、Naoki Kise、Taku Fujimoto、Ayuko Yamanami、Ryoji Nomura

  DOI：10.1021/jo00086a023

  日期：1994.4

  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.