[5,6]-(4-nitrobenz)-1-azacyclodec-3,7-diyne | 1035148-54-9

• 分子结构分类: 有机化合物 - 有机1,3-偶极化合物 - 烯丙基型1,3-偶极有机化合物
• 英文名称: [5,6]-(4-nitrobenz)-1-azacyclodec-3,7-diyne
• 英文别名: 12-Nitro-5-azabicyclo[8.4.0]tetradeca-1(10),11,13-trien-2,8-diyne
• CAS: 1035148-54-9
• 化学式: C₁₃H₁₀N₂O₂
• 分子量: 226.235
• InChiKey: NVKWQLGPOVYWFY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  17
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  57.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  1-[4-nitrophenylsulphonyl]-[5,6]-[4-nitrobenz]-1-aza-cyclodec-3,7-diyne 在 potassium carbonate 、 苯硫酚 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.67h， 以20%的产率得到[5,6]-(4-nitrobenz)-1-azacyclodec-3,7-diyne
  参考文献：
  名称：

  Benzofused N-substituted cyclic enediynes: Activation and DNA-cleavage potential

  摘要：

  The effect of electron withdrawal on the reactivity of N-substituted cyclic enediynes has been studied. These were synthesized via an intramolecular Mitsunobu reaction. The electron withdrawing effect of the nitro groups or the positive charge on the free ammonium salts was found to lower the cyclization temperature for Bergman cyclization. The ammonium salts cleave ds-DNA at nanomolar concentrations. (c) 2008 Published by Elsevier Ltd.

  DOI：

  10.1016/j.bmc.2008.02.044

文献信息

• Benzofused N-substituted cyclic enediynes: Activation and DNA-cleavage potential
  作者：Amit Basak、Moumita Kar

  DOI：10.1016/j.bmc.2008.02.044

  日期：2008.4

  The effect of electron withdrawal on the reactivity of N-substituted cyclic enediynes has been studied. These were synthesized via an intramolecular Mitsunobu reaction. The electron withdrawing effect of the nitro groups or the positive charge on the free ammonium salts was found to lower the cyclization temperature for Bergman cyclization. The ammonium salts cleave ds-DNA at nanomolar concentrations. (c) 2008 Published by Elsevier Ltd.