(3S,4S)-3-Ethyl-4-thiophen-2-yl-azetidin-2-one

• 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: (3S,4S)-3-Ethyl-4-thiophen-2-yl-azetidin-2-one
• 英文别名: (3S,4S)-3-ethyl-4-thiophen-2-ylazetidin-2-one
• 化学式: C₉H₁₁NOS
• 分子量: 181.258
• InChiKey: SSWNGAGJFNGWNI-XPUUQOCRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  57.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  2-噻吩甲醛 、 S-2-Pyridylthiobutanoate 生成 (3S,4S)-3-Ethyl-4-thiophen-2-yl-azetidin-2-one
  参考文献：
  名称：

  Soluble-Polymer-Supported Synthesis ofβ-Lactams on a Modified Poly(ethylene glycol)

  摘要：

  A modified poly(ethylene glycol) (PEG) has been developed for the soluble-polymer-supported synthesis of beta-lactams. The monomethylether of PEG (MeOPEG) with an average M-W of 5000 was used as the support, a 4-(3-propyl)phenyl residue as the spacer, and a 4-oxyphenylamino group as the moiety with the reactive functionality. From this modified PEG representative aromatic, heteroaromatic, unsaturated, and aliphatic imines were obtained in high yields by different procedures. The polymer-supported imines were then employed to prepare several beta-lactams by enolate/imine condensation and ketene/imine cycloaddition. Examples of the control of the absolute stereochemistry during the azetidinone ring formation are also reported. The reactions carried out on the polymer-bound imines showed a remarkable similarity to those performed on nonimmobilized imines, both in terms of yields and stereoselectivities. Removal of the beta-lactams from the polymer has also been accomplished to directly deliver the N-unsubstituted azetidinones.

  DOI：

  10.1002/(sici)1521-3765(20000103)6:1<133::aid-chem133>3.0.co;2-h

文献信息

• Andreoli, Patrizia; Cainelli, Gianfranco; Contento, Michele, Journal of the Chemical Society. Perkin transactions I, 1988, p. 945 - 948
  作者：Andreoli, Patrizia、Cainelli, Gianfranco、Contento, Michele、Giacomini, Daria、Martelli, Giorgio、Panunzio, Mauro

  DOI：——

  日期：——
• A synthetic approach to azetidinones from nitriles and lithiumtriethoxyaluminium hydride.
  作者：P. Andreoli、G. Cainelli、M. Contento、D. Giacomini、G. Martelli、M. Panunzio

  DOI：10.1016/s0040-4039(00)84350-6

  日期：1986.1
• Soluble-Polymer-Supported Synthesis ofβ-Lactams on a Modified Poly(ethylene glycol)
  作者：Rita Annunziata、Maurizio Benaglia、Mauro Cinquini、Franco Cozzi

  DOI：10.1002/(sici)1521-3765(20000103)6:1<133::aid-chem133>3.0.co;2-h

  日期：2000.1.3

  A modified poly(ethylene glycol) (PEG) has been developed for the soluble-polymer-supported synthesis of beta-lactams. The monomethylether of PEG (MeOPEG) with an average M-W of 5000 was used as the support, a 4-(3-propyl)phenyl residue as the spacer, and a 4-oxyphenylamino group as the moiety with the reactive functionality. From this modified PEG representative aromatic, heteroaromatic, unsaturated, and aliphatic imines were obtained in high yields by different procedures. The polymer-supported imines were then employed to prepare several beta-lactams by enolate/imine condensation and ketene/imine cycloaddition. Examples of the control of the absolute stereochemistry during the azetidinone ring formation are also reported. The reactions carried out on the polymer-bound imines showed a remarkable similarity to those performed on nonimmobilized imines, both in terms of yields and stereoselectivities. Removal of the beta-lactams from the polymer has also been accomplished to directly deliver the N-unsubstituted azetidinones.