Methyl-10-keto-11-hydroxyundecanoat | 56078-11-6

• 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: Methyl-10-keto-11-hydroxyundecanoat
• 英文别名: Methyl 11-hydroxy-10-oxoundecanoate；methyl 11-hydroxy-10-oxoundecanoate
• CAS: 56078-11-6
• 化学式: C₁₂H₂₂O₄
• 分子量: 230.304
• InChiKey: NUSVSOSKCHETOQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  16
• 可旋转键数：
  11
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  63.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  10-烯酸甲酯 在 ruthenium trichloride 、 Oxone 、 碳酸氢钠 作用下， 以 水 、 乙腈 为溶剂， 反应 1.1h， 以44%的产率得到methyl 10,11-dihydroxyundecanoate
  参考文献：
  名称：

  Ruthenium-Catalyzed Oxidative Cleavage of Olefins to Aldehydes

  摘要：

  Three oxidation protocols have been developed to cleave olefins to carbonyl compounds with ruthenium trichloride as catalyst (3.5 mol %). These methods convert olefins that are not fully substituted to aldehydes rather than carboxylic acids. While aryl olefins were cleaved to aromatic aldehydes in excellent yields by using the system of RuCl3-Oxone-NaHCO3 in CH3CN-H2O (1.5: 1), aliphatic olefins were converted into alkyl aldehydes with RuCl3-NaIO4 in 1,2-dichloroethane-H2O (1:1) in good to excellent yields. It is noteworthy that terminal aliphatic olefins were cleaved to the corresponding aldehydes in excellent yields by using RuCl3-NaIO4 in CH3CN-H2O (6:1).

  DOI：

  10.1021/jo010122p

文献信息

• Ruthenium-Catalyzed Oxidative Cleavage of Olefins to Aldehydes
  作者：Dan Yang、Chi Zhang

  DOI：10.1021/jo010122p

  日期：2001.7.1

  Three oxidation protocols have been developed to cleave olefins to carbonyl compounds with ruthenium trichloride as catalyst (3.5 mol %). These methods convert olefins that are not fully substituted to aldehydes rather than carboxylic acids. While aryl olefins were cleaved to aromatic aldehydes in excellent yields by using the system of RuCl3-Oxone-NaHCO3 in CH3CN-H2O (1.5: 1), aliphatic olefins were converted into alkyl aldehydes with RuCl3-NaIO4 in 1,2-dichloroethane-H2O (1:1) in good to excellent yields. It is noteworthy that terminal aliphatic olefins were cleaved to the corresponding aldehydes in excellent yields by using RuCl3-NaIO4 in CH3CN-H2O (6:1).