17,23-dichloro-18,22-dinitro-2,5,8,11,14-pentaoxa-26-azatetracyclo[13.9.3.0^19,27.0^21,25]heptacosa-1(24),15,17,19(27),21(25),22-hexaene-20(26H)-one

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 17,23-dichloro-18,22-dinitro-2,5,8,11,14-pentaoxa-26-azatetracyclo[13.9.3.0^19,27.0^21,25]heptacosa-1(24),15,17,19(27),21(25),22-hexaene-20(26H)-one
• 英文别名: 3,21-Dichloro-2,22-dinitro-6,9,12,15,18-pentaoxa-25-azatetracyclo[21.3.1.05,26.019,24]heptacosa-1(26),2,4,19,21,23-hexaen-27-one
• 化学式: C₂₁H₁₉Cl₂N₃O₁₀
• 分子量: 544.302
• InChiKey: AEBLXGMAIJJVCD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  36
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  167
• 氢给体数：
  1
• 氢受体数：
  11

反应信息

• 作为产物：
  描述：

  四乙二醇二对甲苯磺酸酯 在 硝酸 、 乙酸酐 、 氯 、 potassium carbonate 、 溶剂黄146 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 17,23-dichloro-18,22-dinitro-2,5,8,11,14-pentaoxa-26-azatetracyclo[13.9.3.0^19,27.0^21,25]heptacosa-1(24),15,17,19(27),21(25),22-hexaene-20(26H)-one
  参考文献：
  名称：

  Synthesis and X-ray crystallographic studies of novel proton-ionizable nitro- and halogen-substituted acridono-18-crown-6 chromo- and fluorogenic ionophores

  摘要：

  Starting from acridono-18-crown-6 ligand I (Fig. 1) seven new proton-ionizable chromogenic and fluorogenic ionophores 2-8 (Fig. 1) containing NO2 group(s) and/or Br or Cl atom(s) in the aromatic rings were prepared by electrophilic substitution. The precursor macrocycle I was obtained by a modification of the reported procedure which made chromatography unnecessary in purification and gave higher yield. X-ray crystallographic studies of the complexes of acridono-18-crown-6 type ligands 1, 2, 3, 6 and 8 show that the protonionizable units are in the acridone tautomeric form and that the ligands invariably bind a water molecule in their cavities by multipodal hydrogen bonding. In two cases (6 and 8) an additional DMF solvent molecule is also bound at the crown perimeter in the solid state. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2003.09.086

文献信息

• Synthesis and X-ray crystallographic studies of novel proton-ionizable nitro- and halogen-substituted acridono-18-crown-6 chromo- and fluorogenic ionophores
  作者：Péter Huszthy、Borbála Vermes、Nikoletta Báthori、Mátyás Czugler

  DOI：10.1016/j.tet.2003.09.086

  日期：2003.11

  Starting from acridono-18-crown-6 ligand I (Fig. 1) seven new proton-ionizable chromogenic and fluorogenic ionophores 2-8 (Fig. 1) containing NO2 group(s) and/or Br or Cl atom(s) in the aromatic rings were prepared by electrophilic substitution. The precursor macrocycle I was obtained by a modification of the reported procedure which made chromatography unnecessary in purification and gave higher yield. X-ray crystallographic studies of the complexes of acridono-18-crown-6 type ligands 1, 2, 3, 6 and 8 show that the protonionizable units are in the acridone tautomeric form and that the ligands invariably bind a water molecule in their cavities by multipodal hydrogen bonding. In two cases (6 and 8) an additional DMF solvent molecule is also bound at the crown perimeter in the solid state. (C) 2003 Elsevier Ltd. All rights reserved.