5-acetoxy-6-undecanone

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 5-acetoxy-6-undecanone
• 英文别名: 6-Oxoundecan-5-yl acetate；6-oxoundecan-5-yl acetate
• 化学式: C₁₃H₂₄O₃
• 分子量: 228.332
• InChiKey: WTKJMXCBCOXDIS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  16
• 可旋转键数：
  10
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  二正戊基酮 、 溶剂黄146 在 水 碘苯 、 三氟化硼乙醚 、 间氯过氧苯甲酸 作用下， 以58%的产率得到5-acetoxy-6-undecanone
  参考文献：
  名称：

  Iodobenzene-Catalyzed α-Acetoxylation of Ketones. In Situ Generation of Hypervalent (Diacyloxyiodo)benzenes Using m-Chloroperbenzoic Acid

  摘要：

  Reported here for the first time is the iodobenzene-catalyzed alpha-oxidation of ketones, in which diacyloxy(phenyl)-lambda3-iodanes generated in situ act as real oxidants of ketones and m-chloroperbenzoic acid serves as a terminal oxidant. Oxidation of a ketone with m-chloroperbenzoic acid in acetic acid in the presence of a catalytic amount of iodobenzene, BF3.Et2O, and water at room temperature under argon affords an alpha-acetoxy ketone in good yield. p-Methyl- and p-chloroiodobenzene also serve as efficient catalysts in this direct oxidation. We found that when the reaction was carried out in the absence of a catalytic amount of iodobenzene, Baeyer-Villiger oxidation of a ketone took place. It is noted that use of water and BF3.Et2O is crucial to the success of this alpha-acetoxylation.

  DOI：

  10.1021/ja0542800

文献信息

• Iodobenzene-Catalyzed α-Acetoxylation of Ketones. In Situ Generation of Hypervalent (Diacyloxyiodo)benzenes Using <i>m</i>-Chloroperbenzoic Acid
  作者：Masahito Ochiai、Yasunori Takeuchi、Tomoko Katayama、Takuya Sueda、Kazunori Miyamoto

  DOI：10.1021/ja0542800

  日期：2005.9.1

  Reported here for the first time is the iodobenzene-catalyzed alpha-oxidation of ketones, in which diacyloxy(phenyl)-lambda3-iodanes generated in situ act as real oxidants of ketones and m-chloroperbenzoic acid serves as a terminal oxidant. Oxidation of a ketone with m-chloroperbenzoic acid in acetic acid in the presence of a catalytic amount of iodobenzene, BF3.Et2O, and water at room temperature under argon affords an alpha-acetoxy ketone in good yield. p-Methyl- and p-chloroiodobenzene also serve as efficient catalysts in this direct oxidation. We found that when the reaction was carried out in the absence of a catalytic amount of iodobenzene, Baeyer-Villiger oxidation of a ketone took place. It is noted that use of water and BF3.Et2O is crucial to the success of this alpha-acetoxylation.