(3S,4R)-1-(4-methoxyphenyl)-3-methyl-4-[(E)-2-phenylethenyl]-3-phenylsulfanylazetidin-2-one | 135616-48-7

• 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,4R)-1-(4-methoxyphenyl)-3-methyl-4-[(E)-2-phenylethenyl]-3-phenylsulfanylazetidin-2-one
• CAS: 135616-48-7；135682-98-3
• 化学式: C₂₅H₂₃NO₂S
• 分子量: 401.529
• InChiKey: WESBSACYJPSTGU-FPDRDWOUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  29
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.16
• 拓扑面积：
  54.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (3S,4S)-1-(4-methoxyphenyl)-3-methyl-4-[(E)-2-phenylethenyl]-3-phenylsulfanylazetidin-2-one 、 (3S,4R)-1-(4-methoxyphenyl)-3-methyl-4-[(E)-2-phenylethenyl]-3-phenylsulfanylazetidin-2-one 、 二丁基锡烷 生成 (3S,4S)-1-(4-methoxyphenyl)-3-methyl-4-[(E)-2-phenylethenyl]azetidin-2-one
  参考文献：
  名称：

  PALOMO, CLAUDIO;COSSIO, FERNANDO P.;ODIZOLA, JOSE M.;OIARBIDE, MIKEL;ONTO+, J. ORG. CHEM., 56,(1991) N4, C. 4418-4428

  摘要：

  DOI：
• 作为产物：
  描述：

  2-(Phenylthio)propionyl chloride 、 N-(4-Methoxyphenyl)-3-phenylpropenaldimine 生成 (3S,4R)-1-(4-methoxyphenyl)-3-methyl-4-[(E)-2-phenylethenyl]-3-phenylsulfanylazetidin-2-one
  参考文献：
  名称：

  PALOMO, CLAUDIO;COSSIO, FERNANDO P.;ODIZOLA, JOSE M.;OIARBIDE, MIKEL;ONTO+, J. ORG. CHEM., 56,(1991) N4, C. 4418-4428

  摘要：

  DOI：

文献信息

• Preparation of 3-alkyl .beta.-lactams via the ketene imine cycloaddition reaction using .alpha.-(phenylthio)alkanoyl halides as starting materials: application to the synthesis of (.+-.)-carbapenem building blocks and related compounds
  作者：Claudio Palomo、Fernando P. Cossio、Jose M. Odiozola、Mikel Oiarbide、Jesus M. Ontoria

  DOI：10.1021/jo00014a017

  日期：1991.7

  Preparation of appropriately substituted 3-alkyl beta-lactams via the ketene (or equivalent)-imine cycloaddition reaction is described. The dehydrochlorination reaction of alpha-(phenylthio)alkanoyl chlorides with triethylamine in the presence of imines derived from cinnamaldehydes and p-anisidine produced a high-yield formation of alpha-phenylthio beta-lactams, which upon desulfuration furnished a variety of 3-alkyl beta-lactams in a highly stereoselective fashion. In contrast, reaction between alpha-haloalkanoyl chlorides and cinnamylideneamines in the presence of triethylamine furnished the corresponding [4 + 2] cycloadducts as main products. Preparation of highly functionalized alpha-alkylidene beta-lactams through thermal decomposition of the corresponding beta-lactam sulfoxides or by cycloaddition of alpha,beta-unsaturated acid chlorides to imino esters in the presence of triethylamine is also described. Addition of Flemming's silylcuprate reagent to alpha-alkylidene beta-lactams furnished the corresponding 3-(1'-(dimethylphenylsilyl(ethyl) beta-lactams as (+/-)-thienamycin intermediates.