2-hydroxy-3-methyl-N-(2-oxo-2-phenyl-ethyl)-benzamide

• 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-N-(2-oxo-2-phenyl-ethyl)-benzamide
• 英文别名: 2-hydroxy-3-methyl-N-phenacylbenzamide
• 化学式: C₁₆H₁₅NO₃
• 分子量: 269.3
• InChiKey: CIAWSSUBPHPCBZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  66.4
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-hydroxy-3-methyl-N-(2-oxo-2-phenyl-ethyl)-benzamide 在 叔丁基过氧化氢 、 四丁基碘化铵 作用下， 以 水 、 乙酸乙酯 为溶剂， 反应 0.33h， 以54%的产率得到2-benzoyl-8-methyl-2,3-dihydro-benzo[e][1,3]oxazin-4-one
  参考文献：
  名称：

  TBAI-Catalyzed Oxidative Cross-Coupling of Phenols and 2-Aminoacetophenones

  摘要：

  An iodide-catalyzed oxidative cross-coupling between phenols and 2-aminoacetophenones has been developed. Using catalytic amounts of tetrabutylammoniumiodide (TBAI) as an iodine-containing catalyst and aqueous solutions of tert-butyl hydro-peroxide (TBHP) as the stoichiometric co-oxidant, a variety of alpha-phenoxylated 2-aminoacetophenones could be obtained in yields of up to 92% after remarkably short reaction times (20 min). This is a very rare example for an iodide-catalyzed intermolecular cross-coupling utilizing phenols. However, this efficient methodology could be further extended toward an intramolecular variant which gives direct access to a range of dihydro-4H-benzo[e][1,3]oxazin-4-ones.

  DOI：

  10.1021/acs.orglett.5b00466
• 作为产物：
  描述：

  3-甲基水杨酸 、 2-氨基苯乙酮盐酸盐 在 氯化亚砜 、 N,N-二甲基甲酰胺 、 碳酸氢钠 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 5.0h， 以60%的产率得到2-hydroxy-3-methyl-N-(2-oxo-2-phenyl-ethyl)-benzamide
  参考文献：
  名称：

  TBAI-Catalyzed Oxidative Cross-Coupling of Phenols and 2-Aminoacetophenones

  摘要：

  An iodide-catalyzed oxidative cross-coupling between phenols and 2-aminoacetophenones has been developed. Using catalytic amounts of tetrabutylammoniumiodide (TBAI) as an iodine-containing catalyst and aqueous solutions of tert-butyl hydro-peroxide (TBHP) as the stoichiometric co-oxidant, a variety of alpha-phenoxylated 2-aminoacetophenones could be obtained in yields of up to 92% after remarkably short reaction times (20 min). This is a very rare example for an iodide-catalyzed intermolecular cross-coupling utilizing phenols. However, this efficient methodology could be further extended toward an intramolecular variant which gives direct access to a range of dihydro-4H-benzo[e][1,3]oxazin-4-ones.

  DOI：

  10.1021/acs.orglett.5b00466

文献信息

• TBAI-Catalyzed Oxidative Cross-Coupling of Phenols and 2-Aminoacetophenones
  作者：Wei Xu、Boris J. Nachtsheim

  DOI：10.1021/acs.orglett.5b00466

  日期：2015.3.20

  An iodide-catalyzed oxidative cross-coupling between phenols and 2-aminoacetophenones has been developed. Using catalytic amounts of tetrabutylammoniumiodide (TBAI) as an iodine-containing catalyst and aqueous solutions of tert-butyl hydro-peroxide (TBHP) as the stoichiometric co-oxidant, a variety of alpha-phenoxylated 2-aminoacetophenones could be obtained in yields of up to 92% after remarkably short reaction times (20 min). This is a very rare example for an iodide-catalyzed intermolecular cross-coupling utilizing phenols. However, this efficient methodology could be further extended toward an intramolecular variant which gives direct access to a range of dihydro-4H-benzo[e][1,3]oxazin-4-ones.