10-methylheptadecan-8-one | 1443055-90-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 10-methylheptadecan-8-one
• 英文别名: 10-Methylheptadecan-8-one
• CAS: 1443055-90-0
• 化学式: C₁₈H₃₆O
• 分子量: 268.483
• InChiKey: RCTZGMBXFCDNSA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.5
• 重原子数：
  19
• 可旋转键数：
  14
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.94
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  2-壬醇 在 [RuCl₂(p-cymene)(iPr₂-imy)] 、 tricyclohexylphosphine tetrafluoroborate 、 potassium hydroxide 作用下， 以 甲苯 为溶剂， 反应 24.0h， 以94%的产率得到10-methylheptadecan-8-one
  参考文献：
  名称：

  Ruthenium-Catalyzed Self-Coupling of Primary and Secondary Alcohols with the Liberation of Dihydrogen

  摘要：

  The dehydrogenative self-condensation of primary and secondary alcohols has been studied in the presence of RuCl2(IiPr)(p-cymene). The conversion of primary alcohols into esters has been further optimized by using magnesium nitride as an additive, which allows the reaction to take place at a temperature and catalyst loading lower than those described previously. Secondary alcohols were dimerized into racemic ketones by a dehydrogenative Guerbet reaction with potassium hydroxide as the additive. The transformation gave good yields of the ketone diners with a range of alkan-2-ols, whereas more substituted secondary alcohols were unreactive. The reaction proceeds by dehydrogenation to the ketone, followed by an aldol reaction and hydrogenation of the resulting enone.

  DOI：

  10.1021/jo4008699

文献信息

• Ruthenium-Catalyzed Self-Coupling of Primary and Secondary Alcohols with the Liberation of Dihydrogen
  作者：Ilya S. Makarov、Robert Madsen

  DOI：10.1021/jo4008699

  日期：2013.7.5

  The dehydrogenative self-condensation of primary and secondary alcohols has been studied in the presence of RuCl2(IiPr)(p-cymene). The conversion of primary alcohols into esters has been further optimized by using magnesium nitride as an additive, which allows the reaction to take place at a temperature and catalyst loading lower than those described previously. Secondary alcohols were dimerized into racemic ketones by a dehydrogenative Guerbet reaction with potassium hydroxide as the additive. The transformation gave good yields of the ketone diners with a range of alkan-2-ols, whereas more substituted secondary alcohols were unreactive. The reaction proceeds by dehydrogenation to the ketone, followed by an aldol reaction and hydrogenation of the resulting enone.