(4R,5S)-3-[(2R,3S)-2-cyclohexyl-1-(4-methoxyphenyl)-4-oxoazetidin-3-yl]-4,5-diphenyl-1,3-oxazolidin-2-one | 1040390-00-8

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: (4R,5S)-3-[(2R,3S)-2-cyclohexyl-1-(4-methoxyphenyl)-4-oxoazetidin-3-yl]-4,5-diphenyl-1,3-oxazolidin-2-one
• CAS: 1040390-00-8
• 化学式: C₃₁H₃₂N₂O₄
• 分子量: 496.606
• InChiKey: VBEDOKAJIKXVBS-GKQHHHCTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.3
• 重原子数：
  37
• 可旋转键数：
  6
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  59.1
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (4R,5S)-3-[(2R,3S)-2-cyclohexyl-1-(4-methoxyphenyl)-4-oxoazetidin-3-yl]-4,5-diphenyl-1,3-oxazolidin-2-one 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 甲苯 为溶剂， 反应 48.0h， 以96%的产率得到
  参考文献：
  名称：

  A Highly Stereoselective Synthesis of Chiral α-Amino-β-lactams via the Kinugasa Reaction Employing Ynamides

  摘要：

  A highly stereoselective synthesis of chiral alpha-amino-beta-lactam through an ynamide-Kinugasa reaction is described. In addition, a mechanistic model is illustrated here to rationalize the observed diastereoselectivity, which depends on both the initial [3 + 2] cycloaddition step and the subsequent protonation for which both are highly selective.

  DOI：

  10.1021/ol801257j
• 作为产物：
  描述：

  N-(4-methoxyphenyl)-α-cyclohexylnitrone 、 (4R,5S)-3-ethynyl-4,5-diphenyl-1,3-oxazolidin-2-one 在 copper(l) iodide 、 N-甲基二环己基胺 作用下， 以 乙腈 为溶剂， 反应 36.0h， 以62%的产率得到(4R,5S)-3-[(2S,3R)-2-cyclohexyl-1-(4-methoxyphenyl)-4-oxoazetidin-3-yl]-4,5-diphenyl-1,3-oxazolidin-2-one
  参考文献：
  名称：

  A Highly Stereoselective Synthesis of Chiral α-Amino-β-lactams via the Kinugasa Reaction Employing Ynamides

  摘要：

  A highly stereoselective synthesis of chiral alpha-amino-beta-lactam through an ynamide-Kinugasa reaction is described. In addition, a mechanistic model is illustrated here to rationalize the observed diastereoselectivity, which depends on both the initial [3 + 2] cycloaddition step and the subsequent protonation for which both are highly selective.

  DOI：

  10.1021/ol801257j