(E)-2-(3-ethyl-4-phenyl-1-tosylazetidin-2-ylidene)-1-(4-nitrophenyl)ethanone

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (E)-2-(3-ethyl-4-phenyl-1-tosylazetidin-2-ylidene)-1-(4-nitrophenyl)ethanone
• 英文别名: (2E)-2-[(3R,4S)-3-ethyl-1-(4-methylphenyl)sulfonyl-4-phenylazetidin-2-ylidene]-1-(4-nitrophenyl)ethanone
• 化学式: C₂₆H₂₄N₂O₅S
• 分子量: 476.553
• InChiKey: BMYJDWYKISUGOO-PRMNMRSISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  34
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  109
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  1-(4-nitrophenyl)hex-2-yn-1-one 、 N-亚苄基-4-甲基苯磺酰胺 在 4-二甲氨基吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 以42%的产率得到(E)-2-(3-ethyl-4-phenyl-1-tosylazetidin-2-ylidene)-1-(4-nitrophenyl)ethanone
  参考文献：
  名称：

  Cycloaddition of Alkynyl Ketones with N-Tosylimines Catalyzed by Bu₃P and DMAP: Synthesis of Highly Functionalized Pyrrolidines and Azetidines

  摘要：

  Cycloadditions of alkynyl ketones with N-tosylimines catalyzed by Lewis bases to synthesize azetidines and pyrrolidines were systematically described. In the reaction of alkynyl ketones with N-tosylimines catalyzed by Bu3P at room temperature in toluene, highly functionalized pyrrolidines were formed in good to excellent yields. When DMAP was used in place of Bu3P as catalyst to facilitate the cycloaddition, completely substituted azetidines were produced in moderate to good yields in CH2Cl2. Both cyclization reactions proceeded smoothly with complete stereoselectivity. The scope and limitations of these cycloadditon reactions were also investigated.

  DOI：

  10.1021/jo801687v

文献信息

• Cycloaddition of Alkynyl Ketones with <i>N</i>-Tosylimines Catalyzed by Bu₃P and DMAP: Synthesis of Highly Functionalized Pyrrolidines and Azetidines
  作者：Ling-Guo Meng、Peijie Cai、Qingxiang Guo、Song Xue

  DOI：10.1021/jo801687v

  日期：2008.11.7

  Cycloadditions of alkynyl ketones with N-tosylimines catalyzed by Lewis bases to synthesize azetidines and pyrrolidines were systematically described. In the reaction of alkynyl ketones with N-tosylimines catalyzed by Bu3P at room temperature in toluene, highly functionalized pyrrolidines were formed in good to excellent yields. When DMAP was used in place of Bu3P as catalyst to facilitate the cycloaddition, completely substituted azetidines were produced in moderate to good yields in CH2Cl2. Both cyclization reactions proceeded smoothly with complete stereoselectivity. The scope and limitations of these cycloadditon reactions were also investigated.