2-methyl-1,3-diphenyl-pentan-1-one | 857973-57-0

• 分子结构分类: 有机化合物 - 木脂素、新木脂素和相关化合物
• 英文名称: 2-methyl-1,3-diphenyl-pentan-1-one
• 英文别名: α-Methyl-β-aethyl-β-phenyl-propiophenon；2-Methyl-1,3-diphenyl-pentan-1-on；α-Oxo-β-methyl-α.γ-diphenyl-pentan；α-Methyl-β-phenyl-valerophenon；γ-Phenyl-β-benzoyl-pentan；2-Methyl-1,3-diphenylpentan-1-one；2-methyl-1,3-diphenylpentan-1-one
• CAS: 857973-57-0
• 化学式: C₁₈H₂₀O
• 分子量: 252.356
• InChiKey: OXXYAVQWMXZFOP-UHFFFAOYSA-N

物化性质

• 沸点：
  187-188 °C(Press: 16 Torr)
• 密度：
  1.014±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2-methyl-1,3-diphenyl-pentan-1-one 在 sodium amide 、 甲苯 作用下， 生成 3-苯基戊烷
  参考文献：
  名称：

  Albesco, Annales de Chimie (Cachan, France), 1922, vol. <9> 18, p. 221

  摘要：

  DOI：
• 作为产物：
  描述：

  1-苯丙醇 在 [RuCl₂(p-cymene)(iPr₂-imy)] 、 tricyclohexylphosphine tetrafluoroborate 、 potassium hydroxide 作用下， 以 甲苯 为溶剂， 反应 24.0h， 以5%的产率得到2-methyl-1,3-diphenyl-pentan-1-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

• Reynolds, American Chemical Journal, 1910, vol. 44, p. 321
  作者：Reynolds

  DOI：——

  日期：——
• Dimeric Propenyl Phenol Ethers. XVII. The Hydrocarbon Analog of the Cyclic Dimers
  作者：Alexander Muller、Karoly Kormendy

  DOI：10.1021/jo50016a002

  日期：1953.10
• Albesco, Annales de Chimie (Cachan, France), 1922, vol. <9> 18, p. 221
  作者：Albesco

  DOI：——

  日期：——
• 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.