(2S,3R,6S)-2-((S)-1-Azido-propyl)-6-phenyl-5-((S)-1-phenyl-ethyl)-1-oxa-5-aza-spiro[2.3]hexan-4-one | 917110-47-5

• 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: (2S,3R,6S)-2-((S)-1-Azido-propyl)-6-phenyl-5-((S)-1-phenyl-ethyl)-1-oxa-5-aza-spiro[2.3]hexan-4-one
• 英文别名: (2S,3R,6S)-2-[(1S)-1-azidopropyl]-6-phenyl-5-[(1S)-1-phenylethyl]-1-oxa-5-azaspiro[2.3]hexan-4-one
• CAS: 917110-47-5
• 化学式: C₂₁H₂₂N₄O₂
• 分子量: 362.431
• InChiKey: JAUOVIOTNYYPMW-BFNBLTCZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  27
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  47.2
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (2S,3R,6S)-2-((S)-1-Azido-propyl)-6-phenyl-5-((S)-1-phenyl-ethyl)-1-oxa-5-aza-spiro[2.3]hexan-4-one 在 三乙基膦 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以50%的产率得到(3S,4S)-3-((2R,3S)-3-Ethyl-aziridin-2-yl)-3-hydroxy-4-phenyl-1-((S)-1-phenyl-ethyl)-azetidin-2-one
  参考文献：
  名称：

  Synthesis and Biological Evaluation of Azido- and Aziridino-hydroxyl-β-lactams through Stereo- and Regioselective Epoxide Ring Opening

  摘要：

  [GRAPHICS]Two new classes of azido- and aziridino-hydroxyl-beta-lactam containing structures have been prepared by means of a stereo- and regioselective epoxide ring opening. The straightforwardness of the procedure makes this strategy useful for the synthesis of potentially bioactive compounds. Some selected examples showed promising activity in acyl CoA-cholesterol acyltransferase inhibition assays.

  DOI：

  10.1021/jo0615652
• 作为产物：
  描述：

  (1S',3R,4S)-3-bromo-3-but-1-enyl-4-phenyl-1-(1-phenylethyl)azetidin-2-one 在 sodium azide 、 二甲基氯化铝 、 sodium hydride 、 间氯过氧苯甲酸 作用下， 以 正己烷 、 二氯甲烷 、 甲苯 为溶剂， 反应 2.0h， 生成 (2S,3R,6S)-2-((S)-1-Azido-propyl)-6-phenyl-5-((S)-1-phenyl-ethyl)-1-oxa-5-aza-spiro[2.3]hexan-4-one
  参考文献：
  名称：

  Synthesis and Biological Evaluation of Azido- and Aziridino-hydroxyl-β-lactams through Stereo- and Regioselective Epoxide Ring Opening

  摘要：

  [GRAPHICS]Two new classes of azido- and aziridino-hydroxyl-beta-lactam containing structures have been prepared by means of a stereo- and regioselective epoxide ring opening. The straightforwardness of the procedure makes this strategy useful for the synthesis of potentially bioactive compounds. Some selected examples showed promising activity in acyl CoA-cholesterol acyltransferase inhibition assays.

  DOI：

  10.1021/jo0615652

文献信息

• Synthesis and Biological Evaluation of Azido- and Aziridino-hydroxyl-β-lactams through Stereo- and Regioselective Epoxide Ring Opening
  作者：Fides Benfatti、Giuliana Cardillo、Luca Gentilucci、Rossana Perciaccante、Alessandra Tolomelli、Alberico Catapano

  DOI：10.1021/jo0615652

  日期：2006.11.1

  [GRAPHICS]Two new classes of azido- and aziridino-hydroxyl-beta-lactam containing structures have been prepared by means of a stereo- and regioselective epoxide ring opening. The straightforwardness of the procedure makes this strategy useful for the synthesis of potentially bioactive compounds. Some selected examples showed promising activity in acyl CoA-cholesterol acyltransferase inhibition assays.