5,6-diacetoxyhexanoic acid

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 5,6-diacetoxyhexanoic acid
• 英文别名: 5,6-Diacetyloxyhexanoic acid
• 化学式: C₁₀H₁₆O₆
• 分子量: 232.233
• InChiKey: JTZADIKEVKSGAM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  16
• 可旋转键数：
  9
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  89.9
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  1,2-diacetoxyhexan-6-ol 在 potassium bromide 4-(polystyrylMeO)-2,2,6,6-tetraMepiperidin-1-yloxy radical 、 PS-CH₂Me₃(+)*ClO₂(-) 、 PS-CH₂NMe₃(+)*H₂PO₄(-) 作用下， 以 水 、 乙腈 为溶剂， 反应 48.0h， 以98%的产率得到5,6-diacetoxyhexanoic acid
  参考文献：
  名称：

  The simultaneous use of immobilised reagents for the one-pot conversion of alcohols to carboxylic acids

  摘要：

  在单个反应容器中同时使用选定的固定氧化试剂，是将伯醇转化为相应羧酸的有效方法。

  DOI：

  10.1039/b201776h

文献信息

• Triflic Acid Catalyzed Oxidative Lactonization and Diacetoxylation of Alkenes Using Peroxyacids as Oxidants
  作者：Yan-Biao Kang、Lutz H. Gade

  DOI：10.1021/jo202491y

  日期：2012.2.3

  A clean and efficient diacetoxylation reaction of alkenes catalyzed by triflic acid using commercially available peroxyacids as the oxidants has been developed. This method was also applied in oxidative lactonizations of unsaturated carboxylic acids in good to high yields.

  已经开发了使用可商购的过氧酸作为氧化剂的三氟甲磺酸催化的烯烃的清洁且有效的二乙酰氧基化反应。该方法还以高产率到高产率用于不饱和羧酸的氧化内酯化。
• The Nature of the Catalytically Active Species in Olefin Dioxygenation with PhI(OAc)₂: Metal or Proton?
  作者：Yan-Biao Kang、Lutz H. Gade

  DOI：10.1021/ja110805b

  日期：2011.3.16

  Evidence for the protiocatalytic nature of the diacetoxylation of alkenes using PhI(OAc)(2) as oxidant is presented. Systematic studies into the catalytic activity in the presence of proton-trapping and metal-complexing agents indicate that protons act as catalysts in the reaction. Using triflic acid as catalyst, the selectivity and reaction rate of the conversion is similar or superior to most efficient metal-based catalysts. Metal cations, such as Pd(II) and Cu(II), may interact with the oxidant in the initiation phase of the catalytic transformation; however, 1 equiv of strong acid is produced in the first cycle which then functions as the active catalyst. Based on a kinetic study as well as in situ mass spectrometry, a mechanistic cycle for the proton-catalyzed reaction, which is consistent with all experimental data presented in this work, is proposed.
• The simultaneous use of immobilised reagents for the one-pot conversion of alcohols to carboxylic acids
  作者：Kosuke Yasuda、Steven V. Ley

  DOI：10.1039/b201776h

  日期：2002.4.9

  The simultaneous use of selected immobilised oxidising reagents in a single reaction vessel provides an efficient method for the conversion of primary alcohols to the corresponding carboxylic acids.

  在单个反应容器中同时使用选定的固定氧化试剂，是将伯醇转化为相应羧酸的有效方法。