3,3-Diethoxy-4-ethyl-1-(4-nitrophenyl)sulfonylazetidin-2-one | 222406-18-0

• 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: 3,3-Diethoxy-4-ethyl-1-(4-nitrophenyl)sulfonylazetidin-2-one
• CAS: 222406-18-0
• 化学式: C₁₅H₂₀N₂O₇S
• 分子量: 372.399
• InChiKey: HOXWCFKAWACIMI-UHFFFAOYSA-N

物化性质

• 沸点：
  498.851±55.00 °C(Press: 760.00 Torr)(predicted)
• 密度：
  1.397±0.10 g/cm3(Temp: 25 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  25
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  127
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  N-乙酰-L-缬氨酸 、 Fmoc-L-缬氨酸 、 Fmoc-D-亮氨酸 、 3,3-Diethoxy-4-ethyl-1-(4-nitrophenyl)sulfonylazetidin-2-one 、 alkaline earth salt of/the/ methylsulfuric acid 生成
  参考文献：
  名称：

  Solid and solution phase synthesis of α-keto amides via azetidinone ring-opening: Application to the synthesis of poststatin

  摘要：

  3,3-Diethoxy-N-sulfonyl and carbamoyl azetidin-2-ones undergo efficient ring-opening reaction with various amine nucleophiles. Subsequent acid hydrolysis of the ketal moiety generated alpha-keto amides in excellent overall yields. The naturally occurring serine protease inhibitor poststatin was synthesized using this ring-opening reaction as the key step. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(99)00079-9
• 作为产物：
  描述：

  对硝基苯磺酰氯 、 3,3-Diethoxy-4-ethyl-azetidin-2-one 在 sodium hexamethyldisilazane 作用下， 以 四氢呋喃 为溶剂， 以35%的产率得到3,3-Diethoxy-4-ethyl-1-(4-nitrophenyl)sulfonylazetidin-2-one
  参考文献：
  名称：

  Solid and solution phase synthesis of α-keto amides via azetidinone ring-opening: Application to the synthesis of poststatin

  摘要：

  3,3-Diethoxy-N-sulfonyl and carbamoyl azetidin-2-ones undergo efficient ring-opening reaction with various amine nucleophiles. Subsequent acid hydrolysis of the ketal moiety generated alpha-keto amides in excellent overall yields. The naturally occurring serine protease inhibitor poststatin was synthesized using this ring-opening reaction as the key step. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(99)00079-9

文献信息

• Solid and solution phase synthesis of α-keto amides via azetidinone ring-opening: Application to the synthesis of poststatin
  作者：Seock-Kyu Khim、John M. Nuss

  DOI：10.1016/s0040-4039(99)00079-9

  日期：1999.3

  3,3-Diethoxy-N-sulfonyl and carbamoyl azetidin-2-ones undergo efficient ring-opening reaction with various amine nucleophiles. Subsequent acid hydrolysis of the ketal moiety generated alpha-keto amides in excellent overall yields. The naturally occurring serine protease inhibitor poststatin was synthesized using this ring-opening reaction as the key step. (C) 1999 Elsevier Science Ltd. All rights reserved.