N-(chloro(furan-2-yl)methylene)(4-nitrophenyl)methanamine | 1197006-55-5

• 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: N-(chloro(furan-2-yl)methylene)(4-nitrophenyl)methanamine
• 英文别名: N-[(4-nitrophenyl)methyl]furan-2-carboximidoyl chloride
• CAS: 1197006-55-5
• 化学式: C₁₂H₉ClN₂O₃
• 分子量: 264.668
• InChiKey: LQRADEWZIROKJD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  71.3
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-(chloro(furan-2-yl)methylene)(4-nitrophenyl)methanamine 、 (4S)-N-crotonyl-4-phenyloxazolidin-2-one 在 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 以84%的产率得到(2'S,2R,3S,4S)-{[3,4-dihydro-4-methyl-2-(4-nitrophenyl)-5-(furyl-2-yl)-2H-pyrrol-3-yl]-carbonyl}-2-oxo-4-phenyloxazolidine
  参考文献：
  名称：

  Nitrile Ylides: Diastereoselective Cycloadditions using Chiral Oxzolidinones Without Lewis Acid

  摘要：

  Lewis acid complexation is generally required for chiral-auxiliary-controlled stereoselectivity, and chiral Lewis acid catalysis is frequently optimal for introducing asymmetry. In this work, we show that nitrile ylide cycloadditions to electron-poor acceptors attached to chiral auxiliaries proceed in high yield and stereoselectivity In the absence of Lewis acids. In contrast, chiral Lewis acids are inferior in these cycloadditions.

  DOI：

  10.1021/ol9018584
• 作为产物：
  描述：

  Furan-2-carboxylic acid 4-nitro-benzylamide 在 氯化亚砜 作用下， 反应 12.0h， 生成 N-(chloro(furan-2-yl)methylene)(4-nitrophenyl)methanamine
  参考文献：
  名称：

  Nitrile Ylides: Diastereoselective Cycloadditions using Chiral Oxzolidinones Without Lewis Acid

  摘要：

  Lewis acid complexation is generally required for chiral-auxiliary-controlled stereoselectivity, and chiral Lewis acid catalysis is frequently optimal for introducing asymmetry. In this work, we show that nitrile ylide cycloadditions to electron-poor acceptors attached to chiral auxiliaries proceed in high yield and stereoselectivity In the absence of Lewis acids. In contrast, chiral Lewis acids are inferior in these cycloadditions.

  DOI：

  10.1021/ol9018584

文献信息

• Nitrile Ylides: Diastereoselective Cycloadditions using Chiral Oxzolidinones Without Lewis Acid
  作者：Mukund P. Sibi、Takahiro Soeta、Craig P. Jasperse

  DOI：10.1021/ol9018584

  日期：2009.12.3

  Lewis acid complexation is generally required for chiral-auxiliary-controlled stereoselectivity, and chiral Lewis acid catalysis is frequently optimal for introducing asymmetry. In this work, we show that nitrile ylide cycloadditions to electron-poor acceptors attached to chiral auxiliaries proceed in high yield and stereoselectivity In the absence of Lewis acids. In contrast, chiral Lewis acids are inferior in these cycloadditions.