(4S)-3-[(2S,3S)-2-acetyl-1-benzyl-4-oxoazetidin-3-yl]-4-phenyl-1,3-oxazolidin-2-one | 184716-95-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酰胺类
• 英文名称: (4S)-3-[(2S,3S)-2-acetyl-1-benzyl-4-oxoazetidin-3-yl]-4-phenyl-1,3-oxazolidin-2-one
• CAS: 184716-95-8
• 化学式: C₂₁H₂₀N₂O₄
• 分子量: 364.401
• InChiKey: QMQJOHJJCXKEGV-QRVBRYPASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  27
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  66.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (4S)-3-[(2S,3S)-2-acetyl-1-benzyl-4-oxoazetidin-3-yl]-4-phenyl-1,3-oxazolidin-2-one 在 L-Selectride 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 以94%的产率得到(4S)-3-[(2S,3S)-1-benzyl-2-[(1R)-1-hydroxyethyl]-4-oxoazetidin-3-yl]-4-phenyl-1,3-oxazolidin-2-one
  参考文献：
  名称：

  A Study on the Asymmetric Synthesis of β-Lactams through Double Stereodifferentiating Cycloaddition Reactions

  摘要：

  The cycloaddition reaction of chiral aminoketenes, generated from their corresponding acid chlorides and triethylamine, with chiral imines is evaluated as the most direct approach for the construction of cis-beta-lactams with the absolute stereochemistry at the C-3 and C-4 positions being controlled by the ketene partner, independently of the absolute stereochemistry of the imine component.

  DOI：

  10.1021/jo9612180
• 作为产物：
  描述：

  2-(4(S)-phenyloxazolidin-2-on-3-yl)acetyl chloride 在 (Cl₃CO)2CO 、 四丁基氟化铵 、 二甲基亚砜 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 2.25h， 生成 (4S)-3-[(2S,3S)-2-acetyl-1-benzyl-4-oxoazetidin-3-yl]-4-phenyl-1,3-oxazolidin-2-one
  参考文献：
  名称：

  A Study on the Asymmetric Synthesis of β-Lactams through Double Stereodifferentiating Cycloaddition Reactions

  摘要：

  The cycloaddition reaction of chiral aminoketenes, generated from their corresponding acid chlorides and triethylamine, with chiral imines is evaluated as the most direct approach for the construction of cis-beta-lactams with the absolute stereochemistry at the C-3 and C-4 positions being controlled by the ketene partner, independently of the absolute stereochemistry of the imine component.

  DOI：

  10.1021/jo9612180

文献信息

• A Study on the Asymmetric Synthesis of β-Lactams through Double Stereodifferentiating Cycloaddition Reactions
  作者：Claudio Palomo、Jesús M. Aizpurua、Antonia Mielgo、Anthony Linden

  DOI：10.1021/jo9612180

  日期：1996.1.1

  The cycloaddition reaction of chiral aminoketenes, generated from their corresponding acid chlorides and triethylamine, with chiral imines is evaluated as the most direct approach for the construction of cis-beta-lactams with the absolute stereochemistry at the C-3 and C-4 positions being controlled by the ketene partner, independently of the absolute stereochemistry of the imine component.