(E,E)-N-(3-phenylprop-2-en-1-ylidene)-1-(2-pyridyl)methanamine | 1256973-81-5

• 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: (E,E)-N-(3-phenylprop-2-en-1-ylidene)-1-(2-pyridyl)methanamine
• CAS: 1256973-81-5
• 化学式: C₁₅H₁₄N₂
• 分子量: 222.29
• InChiKey: NTKVNWSIXGUJKE-KCJIIOMUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.37
• 重原子数：
  17.0
• 可旋转键数：
  4.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  25.25
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  N-甲基马来酰亚胺 、 (E,E)-N-(3-phenylprop-2-en-1-ylidene)-1-(2-pyridyl)methanamine 在 tetrakis(actonitrile)copper(I) hexafluorophosphate 、 三乙胺 、 2,2′-亚甲基双[(4R,5S)-4,5-二苯基-2-噁唑啉] 作用下， 以 二氯甲烷 为溶剂， 生成 (3aR,4S,6S,6aS)-2-methyl-6-(2-pyridyl)-4-styryl-octahydropyrrolo[3,4-c]pyrrole-1,3-dione 、 (3aS,4R,6R,6aR)-2-methyl-6-(2-pyridyl)-4-styryl-octahydropyrrolo[3,4-c]pyrrole-1,3-dione
  参考文献：
  名称：

  N-(2-Pyridylmethyl)imines as Azomethine Precursors in Catalytic Asymmetric [3 + 2] Cycloadditions

  摘要：

  An efficient Cu(I)-catalyzed asymmetric [3 + 2] cycloaddition of N-(2-pyridylmethyl) imines has been developed. In the presence of a Cu(CH3CN)(4)PF6/bisoxazoline catalyst system, high levels of enantioselectivity (up to 97% ee) and moderate to high exo selectivity were achieved with a wide variety of substituted dipolarophiles, including maleimides, fumarates, fumarodinitrile, enones, and nitroalkenes. The reaction with unsymmetrically substituted dipolarophiles is completely regioselective.

  DOI：

  10.1021/ol102605q
• 作为产物：
  描述：

  反式肉桂醛 、 2-氨甲基吡啶 以 二氯甲烷 为溶剂， 反应 12.0h， 以92%的产率得到(E,E)-N-(3-phenylprop-2-en-1-ylidene)-1-(2-pyridyl)methanamine
  参考文献：
  名称：

  N-(2-Pyridylmethyl)imines as Azomethine Precursors in Catalytic Asymmetric [3 + 2] Cycloadditions

  摘要：

  An efficient Cu(I)-catalyzed asymmetric [3 + 2] cycloaddition of N-(2-pyridylmethyl) imines has been developed. In the presence of a Cu(CH3CN)(4)PF6/bisoxazoline catalyst system, high levels of enantioselectivity (up to 97% ee) and moderate to high exo selectivity were achieved with a wide variety of substituted dipolarophiles, including maleimides, fumarates, fumarodinitrile, enones, and nitroalkenes. The reaction with unsymmetrically substituted dipolarophiles is completely regioselective.

  DOI：

  10.1021/ol102605q