cis-E-4-phenyl-3-styryl-1-tosylazetidin-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: cis-E-4-phenyl-3-styryl-1-tosylazetidin-2-one
• 英文别名: (3S,4S)-1-(4-methylphenyl)sulfonyl-4-phenyl-3-[(E)-2-phenylethenyl]azetidin-2-one
• 化学式: C₂₄H₂₁NO₃S
• 分子量: 403.502
• InChiKey: ZQQOZSQJODHABZ-XUADXGKJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  29.0
• 可旋转键数：
  5.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  54.45
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为产物：
  描述：

  (2R,3R)-2-phenyl-3-[(E)-2-phenyl-1-ethenyl]-1-tosylaziridine 在 tris(dibenzylideneacetone)dipalladium(0) chloroform complex 、 三苯基膦 、 四丁基二氟三苯硅酸铵 作用下， 以 甲苯 为溶剂， 20.0 ℃ 、100.0 kPa 条件下， 反应 50.0h， 生成 trans-(E)-4-phenyl-3-styryl-1-tosylazetidin-2-one 、 cis-E-4-phenyl-3-styryl-1-tosylazetidin-2-one 、 trans-Z-4-phenyl-3-styryl-1-tosylazetidin-2-one
  参考文献：
  名称：

  Palladium-Catalyzed Insertion of CO₂ into Vinylaziridines: New Route to 5-Vinyloxazolidinones

  摘要：

  2-Vinylaziridines undergo a mild Pd-catalyzed ring-opening cyclization reaction with an ambient atmosphere of carbon dioxide to give 5-vinyloxazolidinones. The process is high yielding as well as regio- and stereoselective.

  DOI：

  10.1021/ol201193d

文献信息

• Isothiourea-Mediated Asymmetric Functionalization of 3-Alkenoic Acids
  作者：Louis C. Morrill、Samuel M. Smith、Alexandra M. Z. Slawin、Andrew D. Smith

  DOI：10.1021/jo402591v

  日期：2014.2.21

  Isothiourea HBTM-2.1 promotes the catalytic asymmetric alpha-functionalization of 3-alkenoic acids through formal [2 + 2] cycloadditions with N-tosyl aldimines and formal [4 + 2] cycloadditions with either 4-aryltrifluoromethyl enones or N-aryl-N-aroyl diazenes, providing useful synthetic building blocks in good yield and with excellent enantiocontrol (up to >99% ee). Stereodefined products are amenable to further synthetic elaboration through manipulation of the olefinic functionality.
• Palladium-Catalyzed Insertion of CO₂ into Vinylaziridines: New Route to 5-Vinyloxazolidinones
  作者：Francesco Fontana、C. Chun Chen、Varinder K. Aggarwal

  DOI：10.1021/ol201193d

  日期：2011.7.1

  2-Vinylaziridines undergo a mild Pd-catalyzed ring-opening cyclization reaction with an ambient atmosphere of carbon dioxide to give 5-vinyloxazolidinones. The process is high yielding as well as regio- and stereoselective.