(S)-3-[(R)-2-Azido-but-(E)-ylidene]-4-phenyl-1-((S)-1-phenyl-ethyl)-azetidin-2-one | 847981-57-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氮杂环丁烷
• 英文名称: (S)-3-[(R)-2-Azido-but-(E)-ylidene]-4-phenyl-1-((S)-1-phenyl-ethyl)-azetidin-2-one
• 英文别名: (3E,4S)-3-[(2R)-2-azidobutylidene]-4-phenyl-1-[(1S)-1-phenylethyl]azetidin-2-one
• CAS: 847981-57-1
• 化学式: C₂₁H₂₂N₄O
• 分子量: 346.432
• InChiKey: NGTLUFPDCJWFTQ-CGDQOGJOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  26
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  34.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (S)-3-[(R)-2-Azido-but-(E)-ylidene]-4-phenyl-1-((S)-1-phenyl-ethyl)-azetidin-2-one 在 palladium on activated charcoal 氢气 作用下， 生成 (3R,4R)-3-((R)-2-Amino-butyl)-4-phenyl-1-((S)-1-phenyl-ethyl)-azetidin-2-one
  参考文献：
  名称：

  Highly Diastereoselective Allylic Azide Formation and Isomerization. Synthesis of 3(2‘-Amino)-β-lactams

  摘要：

  The stereoselective anti S(N)2' attack of NaN3 to 3-alkenyl-3-bromo-azetidin-2-ones gave a mixture of diastereomeric azides in fast equilibrium. The [3,3]-sigmatropic rearrangement of allylic azides occurred with complete stereocontrol, allowing the equilibrium to be directed preferentially toward the (E)- or (Z)-isomer, useful precursors of 3(2'-amino)-beta-lactams.

  DOI：

  10.1021/ol047815n
• 作为产物：
  描述：

  (S)-3-[(S)-2-Azido-but-(Z)-ylidene]-4-phenyl-1-((S)-1-phenyl-ethyl)-azetidin-2-one 生成 (S)-3-[(R)-2-Azido-but-(E)-ylidene]-4-phenyl-1-((S)-1-phenyl-ethyl)-azetidin-2-one
  参考文献：
  名称：

  Highly Diastereoselective Allylic Azide Formation and Isomerization. Synthesis of 3(2‘-Amino)-β-lactams

  摘要：

  The stereoselective anti S(N)2' attack of NaN3 to 3-alkenyl-3-bromo-azetidin-2-ones gave a mixture of diastereomeric azides in fast equilibrium. The [3,3]-sigmatropic rearrangement of allylic azides occurred with complete stereocontrol, allowing the equilibrium to be directed preferentially toward the (E)- or (Z)-isomer, useful precursors of 3(2'-amino)-beta-lactams.

  DOI：

  10.1021/ol047815n