2-hydroxy-3-methyl-1-(2-methylphenyl)-1-butanone | 799804-39-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-hydroxy-3-methyl-1-(2-methylphenyl)-1-butanone
• 英文别名: 2-Hydroxy-3-methyl-1-(2-methylphenyl)butan-1-one
• CAS: 799804-39-0
• 化学式: C₁₂H₁₆O₂
• 分子量: 192.258
• InChiKey: KQDQFMDUFJFWNV-UHFFFAOYSA-N

物化性质

• 沸点：
  296.3±15.0 °C(Predicted)
• 密度：
  1.039±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-hydroxy-3-methyl-1-(2-methylphenyl)-1-butanone 在 吡啶 、 N-甲基咪唑 作用下， 以 甲醇 为溶剂， 反应 16.0h， 生成 1-茚酮
  参考文献：
  名称：

  Photochemical Preparation of Highly Functionalized 1-Indanones

  摘要：

  A series of o-alkylphenyl alkyl ketones I were synthesized by different methods. The presence of a leaving group X adjacent to the carbonyl group is the special peculiarity of these ketones. Upon irradiation the keto carbonyl group of these compounds undergoes an n-pi* excitation followed by a 1,5-hydrogen migration from the o-alkyl substituent to the carbonyl oxygen atom. The thus formed 1,4-diradicals are subject to a very rapid elimination of acid HX, giving 1,5-diradicals. We called this process spin center shift. After intersystem crossing these diradicals cyclize to 1-indanones 20 in good yields. Depending on the solvent and on substituents, o-alkoxyalkyl ketones 22 or benzo[c]furanes 21 are obtained as byproducts. The mechanism of the cyclization was elucidated by quantum chemical calculations and kinetic measurements.

  DOI：

  10.1021/jo040173x
• 作为产物：
  描述：

  2-甲基苯甲醛 在 正丁基锂 、 Montmorillonite-K 10 、 二异丙胺 作用下， 以 乙醚 、 正己烷 为溶剂， 反应 78.75h， 生成 2-hydroxy-3-methyl-1-(2-methylphenyl)-1-butanone
  参考文献：
  名称：

  Photochemical Preparation of Highly Functionalized 1-Indanones

  摘要：

  A series of o-alkylphenyl alkyl ketones I were synthesized by different methods. The presence of a leaving group X adjacent to the carbonyl group is the special peculiarity of these ketones. Upon irradiation the keto carbonyl group of these compounds undergoes an n-pi* excitation followed by a 1,5-hydrogen migration from the o-alkyl substituent to the carbonyl oxygen atom. The thus formed 1,4-diradicals are subject to a very rapid elimination of acid HX, giving 1,5-diradicals. We called this process spin center shift. After intersystem crossing these diradicals cyclize to 1-indanones 20 in good yields. Depending on the solvent and on substituents, o-alkoxyalkyl ketones 22 or benzo[c]furanes 21 are obtained as byproducts. The mechanism of the cyclization was elucidated by quantum chemical calculations and kinetic measurements.

  DOI：

  10.1021/jo040173x