8-oxonon-3-enoic acid | 73127-65-8

• 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: 8-oxonon-3-enoic acid
• CAS: 73127-65-8
• 化学式: C₉H₁₄O₃
• 分子量: 170.208
• InChiKey: ZUDNDYNELIKCOB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.78
• 重原子数：
  12.0
• 可旋转键数：
  6.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  54.37
• 氢给体数：
  1.0
• 氢受体数：
  2.0

反应信息

• 作为产物：
  描述：

  6-oxoheptanal 、 丙二酸 在 四氢吡咯 、 吡啶 作用下， 以 四氢呋喃 为溶剂， 以570 mg的产率得到(E)-8-oxo-non-2-enoic acid
  参考文献：
  名称：

  使用一锅加氢甲酰化/脱羧 Knoevenagel 反应序列实际合成 (E)-α,β-不饱和羧酸

  摘要：

  AbstractCombining the regioselective room temperature/ambient pressure hydroformylation and a modification of the Doebner–Knoevenagel reaction allowed for the development of an efficient, one‐pot procedure for the synthesis of (E)‐α,β‐unsaturated carboxylic acids. The reaction proceeds under mild conditions, tolerates a variety of functional groups and gives (E)‐α,β‐unsaturated carboxylic acids in good yields and with excellent regio‐ and stereocontrol. The practicability of this process has been demonstrated by a short protecting group‐free synthesis of the queen honeybee pheromones 9‐ODA [(E)‐9‐oxodec‐2‐enoic acid] and 9‐HDA [(E)‐9‐hydroxydec‐2‐enoic acid].

  DOI：

  10.1002/adsc.200700595

文献信息

• Practical Synthesis of (E)-α,β-Unsaturated Carboxylic Acids Using a One-Pot Hydroformylation/Decarboxylative Knoevenagel Reaction Sequence
  作者：Susanne T. Kemme、Tomáš Šmejkal、Bernhard Breit

  DOI：10.1002/adsc.200700595

  日期：2008.5.5

  AbstractCombining the regioselective room temperature/ambient pressure hydroformylation and a modification of the Doebner–Knoevenagel reaction allowed for the development of an efficient, one‐pot procedure for the synthesis of (E)‐α,β‐unsaturated carboxylic acids. The reaction proceeds under mild conditions, tolerates a variety of functional groups and gives (E)‐α,β‐unsaturated carboxylic acids in good yields and with excellent regio‐ and stereocontrol. The practicability of this process has been demonstrated by a short protecting group‐free synthesis of the queen honeybee pheromones 9‐ODA [(E)‐9‐oxodec‐2‐enoic acid] and 9‐HDA [(E)‐9‐hydroxydec‐2‐enoic acid].