(6S)-2-cyclopropyl-N-diphenylmethyl-6-[(1R)-1-hydroxyethyl]-2,3-dehydromorpholin-5-one

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (6S)-2-cyclopropyl-N-diphenylmethyl-6-[(1R)-1-hydroxyethyl]-2,3-dehydromorpholin-5-one
• 英文别名: (2S)-4-benzhydryl-6-cyclopropyl-2-[(1R)-1-hydroxyethyl]-1,4-oxazin-3-one
• 化学式: C₂₂H₂₃NO₃
• 分子量: 349.43
• InChiKey: PNEJJIFGXAJNHQ-VFNWGFHPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  26
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  49.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2-溴-1-环丙基乙酮 在 草酰氯 、 potassium carbonate 、 potassium iodide 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 11.0h， 生成 (6S)-2-cyclopropyl-N-diphenylmethyl-6-[(1R)-1-hydroxyethyl]-2,3-dehydromorpholin-5-one
  参考文献：
  名称：

  Regioselective Baeyer−Villiger Oxidation in 4-Carbonyl-2-azetidinone Series: A Revisited Route toward Carbapenem Precursor

  摘要：

  A novel synthesis of acetoxyazetidinone 2 is presented. The azetidinone ring of compounds 7 is formed by C-3/C-4 cyclization of (2R,3R)-epoxybutyramide precursors 6, N-protected with a benzhydryl group. N-Deprotection by photoactivated bromination and acidic treatment leads to compounds 10 with various CO-R substituents at C-4. Transformation of these substituents by Baeyer-Villiger oxidation gives the desired regioisomer 11 with the cyclopropyl side-group which is the only group (among R = H, Ph, t-Bu, i-Pr, c-Pr) able to satisfy both the steric requirements of the cyclization step and the electronic requirements of the oxidative rearrangement step.

  DOI：

  10.1021/jo030377y

文献信息

• Regioselective Baeyer−Villiger Oxidation in 4-Carbonyl-2-azetidinone Series: A Revisited Route toward Carbapenem Precursor
  作者：Mathieu Laurent、Marcel Cérésiat、Jacqueline Marchand-Brynaert

  DOI：10.1021/jo030377y

  日期：2004.4.1

  A novel synthesis of acetoxyazetidinone 2 is presented. The azetidinone ring of compounds 7 is formed by C-3/C-4 cyclization of (2R,3R)-epoxybutyramide precursors 6, N-protected with a benzhydryl group. N-Deprotection by photoactivated bromination and acidic treatment leads to compounds 10 with various CO-R substituents at C-4. Transformation of these substituents by Baeyer-Villiger oxidation gives the desired regioisomer 11 with the cyclopropyl side-group which is the only group (among R = H, Ph, t-Bu, i-Pr, c-Pr) able to satisfy both the steric requirements of the cyclization step and the electronic requirements of the oxidative rearrangement step.