1-benzyl-3-(tert-butyloxycarbonylaminomethyl)azetidin-2-one | 1578255-41-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 英文名称: 1-benzyl-3-(tert-butyloxycarbonylaminomethyl)azetidin-2-one
• CAS: 1578255-41-0
• 化学式: C₁₆H₂₂N₂O₃
• 分子量: 290.362
• InChiKey: ULTPVPLPFZJRCH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.17
• 重原子数：
  21.0
• 可旋转键数：
  4.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  58.64
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  1-benzyl-3-(tert-butyloxycarbonylaminomethyl)azetidin-2-one 在 氨 、 sodium 作用下， 以 乙醇 为溶剂， 反应 0.25h， 以71%的产率得到3-(tert-butyloxycarbonylaminomethyl)azetidin-2-one
  参考文献：
  名称：

  Structure–Activity Relationships among Antifungal Nylon-3 Polymers: Identification of Materials Active against Drug-Resistant Strains of Candida albicans

  摘要：

  Fungal infections are a major challenge to human health that is heightened by pathogen resistance to current therapeutic agents. Previously, we were inspired by host-defense peptides to develop nylon-3 polymers (poly-β-peptides) that are toxic toward the fungal pathogen Candida albicans but exert little effect on mammalian cells. Based on subsequent analysis of structure-activity relationships among antifungal nylon-3 polymers, we have now identified readily prepared cationic homopolymers active against strains of C. albicans that are resistant to the antifungal drugs fluconazole and amphotericin B. These nylon-3 polymers are nonhemolytic. In addition, we have identified cationic-hydrophobic copolymers that are highly active against a second fungal pathogen, Cryptococcus neoformans, and moderately active against a third pathogen, Aspergillus fumigatus.

  DOI：

  10.1021/ja500036r
• 作为产物：
  描述：

  1-benzyl-3-((p-toluenesulfonyloxy)methyl)azetidin-2-one 在 sodium azide 、 10 wt% Pd(OH)2 on carbon 、 氢气 、 三乙胺 作用下， 以 甲醇 、 乙醇 、 水 为溶剂， 20.0~60.0 ℃ 、101.33 kPa 条件下， 反应 10.0h， 生成 1-benzyl-3-(tert-butyloxycarbonylaminomethyl)azetidin-2-one
  参考文献：
  名称：

  Structure–Activity Relationships among Antifungal Nylon-3 Polymers: Identification of Materials Active against Drug-Resistant Strains of Candida albicans

  摘要：

  Fungal infections are a major challenge to human health that is heightened by pathogen resistance to current therapeutic agents. Previously, we were inspired by host-defense peptides to develop nylon-3 polymers (poly-β-peptides) that are toxic toward the fungal pathogen Candida albicans but exert little effect on mammalian cells. Based on subsequent analysis of structure-activity relationships among antifungal nylon-3 polymers, we have now identified readily prepared cationic homopolymers active against strains of C. albicans that are resistant to the antifungal drugs fluconazole and amphotericin B. These nylon-3 polymers are nonhemolytic. In addition, we have identified cationic-hydrophobic copolymers that are highly active against a second fungal pathogen, Cryptococcus neoformans, and moderately active against a third pathogen, Aspergillus fumigatus.

  DOI：

  10.1021/ja500036r