dimethyl [(αS,3S)-3-(1-acetoxyethyl)-1-(4-methoxyphenyl)-4-oxoazetidin-2,2-dicarboxylate] | 341554-40-3

• 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: dimethyl [(αS,3S)-3-(1-acetoxyethyl)-1-(4-methoxyphenyl)-4-oxoazetidin-2,2-dicarboxylate]
• CAS: 341554-40-3
• 化学式: C₁₈H₂₁NO₈
• 分子量: 379.367
• InChiKey: RIKFTHOYTXVLBW-HZMBPMFUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.69
• 重原子数：
  27.0
• 可旋转键数：
  6.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  108.44
• 氢给体数：
  0.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  dimethyl [(αS,3S)-3-(1-acetoxyethyl)-1-(4-methoxyphenyl)-4-oxoazetidin-2,2-dicarboxylate] 在 吡啶 、 sodium hydroxide 作用下， 以58%的产率得到(αS,3S)-3-(1-acetoxyethyl)-2-methoxycarbonyl-1-(4-methoxyphenyl)-4-oxoazetidin-2-carboxylic acid
  参考文献：
  名称：

  Synthesis of pure methyl [(2S,3R,αR)-1-(3-bromo-4-methoxyphenyl)-3-(α-acetoxy)ethyl-4-oxoazetidin-2-carboxylate] and its enantiomer

  摘要：

  Synthesis of key intermediates leading to 2-iso-oxacephems was carried out starting from L- and D-threonine. As predicted in our previous paper (Tetrahedron Lett. 1995, 36, 8303-8306) all diastereomers of 2-iso-oxacephems can be prepared from the appropriate enantiomers of the amino acid threonine. The absolute configuration of the 2,3- and alpha -carbon atoms in the beta -lactam structure was determined by X-ray crystallographic studies. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(01)00003-9
• 作为产物：
  描述：

  (2R,3S)-3-Acetoxy-2-bromo-butyric acid 在 氯化亚砜 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 二氯甲烷 、 甲苯 、 苯 为溶剂， 反应 56.0h， 生成 dimethyl [(αS,3S)-3-(1-acetoxyethyl)-1-(4-methoxyphenyl)-4-oxoazetidin-2,2-dicarboxylate]
  参考文献：
  名称：

  Synthesis of pure methyl [(2S,3R,αR)-1-(3-bromo-4-methoxyphenyl)-3-(α-acetoxy)ethyl-4-oxoazetidin-2-carboxylate] and its enantiomer

  摘要：

  Synthesis of key intermediates leading to 2-iso-oxacephems was carried out starting from L- and D-threonine. As predicted in our previous paper (Tetrahedron Lett. 1995, 36, 8303-8306) all diastereomers of 2-iso-oxacephems can be prepared from the appropriate enantiomers of the amino acid threonine. The absolute configuration of the 2,3- and alpha -carbon atoms in the beta -lactam structure was determined by X-ray crystallographic studies. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(01)00003-9