ethoxycarbonyl 2-<(2R,S_S)-2-benzylsulfinamoyl-4-oxoazetidin-1-yl>-3-methylbut-2-enoate | 157027-17-3

• 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: ethoxycarbonyl 2-<(2R,S_S)-2-benzylsulfinamoyl-4-oxoazetidin-1-yl>-3-methylbut-2-enoate
• 英文别名: ethoxycarbonyl 2-((2R,S_S)-2-benzylsulfinamoyl-4-oxoazetidin-1-yl)-3-methylbut-2-enoate
• CAS: 157027-17-3
• 化学式: C₁₈H₂₂N₂O₆S
• 分子量: 394.448
• InChiKey: YVZPHBHCLKKWQV-RXAIFQJESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.99
• 重原子数：
  27.0
• 可旋转键数：
  7.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  102.01
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  ethoxycarbonyl 2-<(2R,S_S)-2-benzylsulfinamoyl-4-oxoazetidin-1-yl>-3-methylbut-2-enoate 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以32%的产率得到(5R,6R)-4-benzyl-2-isopropylidene-5-oxo-5-thia-1,4-diazabicyclo<4.2.0>octane-3,8-dione
  参考文献：
  名称：

  Synthesis, structural characterization and stereocontrolled degradation of 2-azacephams

  摘要：

  The enantiomerically pure substituted 2-azacephams 5 were synthesized by intramolecular cyclization of sulfinamides 4. Their absolute configurations were confirmed by X-ray crystal structure: determination of (5R,6R)-4-benzyl-2-isopropylidene-5-oxo-5-thia-1,4-diazabicyclo[4.2.0]octane-3,8-dione 5a. Nucleophilic opening of 2-azacephams by methanol occurred rapidly to give sulfinates 8 with excellent regio and stereoselectivity,

  DOI：

  10.1016/0957-4166(94)80131-2
• 作为产物：
  描述：

  benzyl 2-<(2R,S_S)-2-benzylsulphinamoyl-4-oxoazetidin-1-yl>-3-methylbut-2-enoate 在 三氯化铝 、 苯甲醚 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 生成 ethoxycarbonyl 2-<(2R,S_S)-2-benzylsulfinamoyl-4-oxoazetidin-1-yl>-3-methylbut-2-enoate
  参考文献：
  名称：

  Synthesis, structural characterization and stereocontrolled degradation of 2-azacephams

  摘要：

  The enantiomerically pure substituted 2-azacephams 5 were synthesized by intramolecular cyclization of sulfinamides 4. Their absolute configurations were confirmed by X-ray crystal structure: determination of (5R,6R)-4-benzyl-2-isopropylidene-5-oxo-5-thia-1,4-diazabicyclo[4.2.0]octane-3,8-dione 5a. Nucleophilic opening of 2-azacephams by methanol occurred rapidly to give sulfinates 8 with excellent regio and stereoselectivity,

  DOI：

  10.1016/0957-4166(94)80131-2

文献信息

• Functional derivatives of 4-oxoazetidine-2-sulfinic acids in asymmetric synthesis of 2-azacepham sulfoxides and their transformation
  作者：Jure J. Herak、Mladen Vinković、Irena Lukić

  DOI：10.1016/0040-4020(95)98705-m

  日期：1995.4

  presence of dry hydrogen chloride followed by triethylamine. The cyclization accrued via equilibrated mixtures of sulfinyl chlorides , which presence was confirmed by chemical transformations. The absolute configuration of the sulfinic acid 9a as a product of their hydrolysis was determinate by a single crystal X-ray analysis.

  对映体纯的2-氮杂庚烷亚砜2a是在干燥的氯化氢，然后是三乙胺的存在下，通过亚砜3或亚磺酰胺8的立体控制的分子内环化反应合成的。环化反应是通过亚磺酰氯的平衡混合物实现的，化学转化证实了该混合物的存在。通过单晶X射线分析确定作为其水解产物的亚磺酸9a的绝对构型。