3,3-Diethoxy-4-ethyl-azetidin-2-one | 222406-13-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3,3-Diethoxy-4-ethyl-azetidin-2-one
• CAS: 222406-13-5
• 化学式: C₉H₁₇NO₃
• 分子量: 187.239
• InChiKey: YPDYQARDDYRFBJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.66
• 重原子数：
  13.0
• 可旋转键数：
  5.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  47.56
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  3,3-Diethoxy-4-ethyl-azetidin-2-one 在 sodium hexamethyldisilazane 作用下， 以 四氢呋喃 为溶剂， 反应 10.0h， 生成 (S)-2-[2,2-Diethoxy-3-(toluene-4-sulfonylamino)-pentanoylamino]-3-phenyl-propionic acid
  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：

  丙醛 、 2,2-二乙氧基乙酸乙酯 在 lithium hexamethyldisilazane 、 lithium diisopropyl amide 作用下， 以68%的产率得到3,3-Diethoxy-4-ethyl-azetidin-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