1-(2'-indanyloxycarbonyl)-(3S)-(t-butoxycarbonyl)aminoazetidin-2-one | 525584-17-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯氮卓类
• 英文名称: 1-(2'-indanyloxycarbonyl)-(3S)-(t-butoxycarbonyl)aminoazetidin-2-one
• CAS: 525584-17-2
• 化学式: C₁₈H₂₂N₂O₅
• 分子量: 346.383
• InChiKey: UEJHSZPGARKBPC-AWEZNQCLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.03
• 重原子数：
  25.0
• 可旋转键数：
  2.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  84.94
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  1-(2'-indanyloxycarbonyl)-(3S)-(t-butoxycarbonyl)aminoazetidin-2-one 在 硫酸 、 potassium bromide 、 sodium nitrite 作用下， 以 甲醇 、 二氯甲烷 、 水 为溶剂， 反应 3.5h， 生成 1-(2'-indanyloxycarbonyl)-3-bromoazetidin-2-one
  参考文献：
  名称：

  1-Alkoxycarbonyl-3-halogenoazetidin-2-ones as elastase (PPE) inhibitors

  摘要：

  A series of 1-alkoxycarbonyl-3-halogenoazetidin-2-ones, designed as potential suicide inhibitors of serine proteases, has been synthesized and evaluated against porcine pancreatic elastase (PPE). All the compounds were transient inhibitors, their activity depending mainly on the nature of the halogen substituent: bromo- and iodo-derivatives are more active (K-i similar to2-22 muM) than 3-chloroazetidinones (K-i similar to20-150 muM). The lipophilicity of the N-1 substituent appeared to exert a slightly positive effect. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(02)00304-8
• 作为产物：
  描述：

  (S)-3-[[(1,1-dimethylethoxy)carbonyl]amino]azetidin-2-one 、 2-indanyl chloroformate 在 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 为溶剂， 反应 2.5h， 以33%的产率得到1-(2'-indanyloxycarbonyl)-(3S)-(t-butoxycarbonyl)aminoazetidin-2-one
  参考文献：
  名称：

  1-Alkoxycarbonyl-3-halogenoazetidin-2-ones as elastase (PPE) inhibitors

  摘要：

  A series of 1-alkoxycarbonyl-3-halogenoazetidin-2-ones, designed as potential suicide inhibitors of serine proteases, has been synthesized and evaluated against porcine pancreatic elastase (PPE). All the compounds were transient inhibitors, their activity depending mainly on the nature of the halogen substituent: bromo- and iodo-derivatives are more active (K-i similar to2-22 muM) than 3-chloroazetidinones (K-i similar to20-150 muM). The lipophilicity of the N-1 substituent appeared to exert a slightly positive effect. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(02)00304-8