32-Methoxy-8-nitro-18,21,26,29-tetraoxa-1,4,12,15-tetraaza-tricyclo[13.8.8.1^6,10]dotriaconta-6,8,10(32)-triene-3,13-dione | 185455-08-7

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 大环内酰胺类
• 英文名称: 32-Methoxy-8-nitro-18,21,26,29-tetraoxa-1,4,12,15-tetraaza-tricyclo[13.8.8.1^6,10]dotriaconta-6,8,10(32)-triene-3,13-dione
• 英文别名: 32-Methoxy-8-nitro-18,21,26,29-tetraoxa-1,4,12,15-tetrazatricyclo[13.8.8.16,10]dotriaconta-6,8,10(32)-triene-3,13-dione
• CAS: 185455-08-7
• 化学式: C₂₅H₃₉N₅O₉
• 分子量: 553.613
• InChiKey: GXLFGRWMAFCLDG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1
• 重原子数：
  39
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.68
• 拓扑面积：
  157
• 氢给体数：
  2
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  32-Methoxy-8-nitro-18,21,26,29-tetraoxa-1,4,12,15-tetraaza-tricyclo[13.8.8.1^6,10]dotriaconta-6,8,10(32)-triene-3,13-dione 在 lithium iodide 作用下， 以 吡啶 为溶剂， 以70%的产率得到32-hydroxy-8-nitro-18,21,26,29-tetraoxa-1,4,12,15-tetraazatricyclo[13.8.8.1^6,10]dotriaconta-6,8,10(32)-triene-3,13-dione
  参考文献：
  名称：

  Synthesis of Proton-Ionizable p-Nitrophenol-Containing Tetraazacrown and Diazadithiacrown Ethers from an Aromatic Building Block Prepared via the Einhorn Reaction

  摘要：

  A series of p-nitroanisole-containing tetraazacrown (14-18), diazacryptand (22), and diazadithia-crown (23-25) macrocycles has been prepared by treating the appropriate secondary diamine, diazacrown, or dimercaptan with 2,6-bis[(2 -chloroacetamido)methyl]-4-nitroanisole (BB). Five of these p-nitroanisole-containing macrocycles were reported earlier. Four new bis(p-nitroanisole)-containing macrocycles resulting from a 2 + 2 macrocyclization of diamine or dimercaptan with BE were also isolated. Six of the p-nitroanisole-containing macrocycles (16, 17, 22-25) were converted to the p-nitrophenol-containing macrocycles (27-32) on treatment with LiI in refluxing pyridine. Thermodynamic quantities (log K, Delta H, and T Delta S) for the interactions of four new compounds (24, 27, 31, and 32) with Na+, K+, Ba2+, Ag+, and Pb2+ were evaluated by calorimetric titration at 25.0 degrees C in either 70% or absolute methanol solution. The compounds show strong interactions with Ag+ and Pb2+ but very weak interactions with Na+, K+, and Ba2+. Ligand 31 exhibited high selectivity for Ag+ over Pb2+. X-ray crystal structures were obtained for diazadithia macrocycle 23 and the Ag+-31 complex.

  DOI：

  10.1021/jo980414z
• 作为产物：
  描述：

  二氮杂18-冠醚-6 、 2-chloro-N-[[3-[[(2-chloroacetyl)amino]methyl]-2-methoxy-5-nitrophenyl]methyl]acetamide 在 sodium carbonate 作用下， 以 乙腈 为溶剂， 以62%的产率得到32-Methoxy-8-nitro-18,21,26,29-tetraoxa-1,4,12,15-tetraaza-tricyclo[13.8.8.1^6,10]dotriaconta-6,8,10(32)-triene-3,13-dione
  参考文献：
  名称：

  Einhorn Reaction for the Synthesis of Aromatic Building Blocks for Macrocyclization

  摘要：

  DOI：

  10.1021/jo9617070

文献信息

• Einhorn Reaction for the Synthesis of Aromatic Building Blocks for Macrocyclization
  作者：Victor N. Pastushok、Kejiang Hu、Jerald S. Bradshaw、N. Kent Dalley、Andrei V. Bordunov、Nikolai G. Lukyanenko

  DOI：10.1021/jo9617070

  日期：1997.1.1
• Synthesis of Proton-Ionizable <i>p</i>-Nitrophenol-Containing Tetraazacrown and Diazadithiacrown Ethers from an Aromatic Building Block Prepared via the Einhorn Reaction
  作者：Kejiang Hu、Jerald S. Bradshaw、Victor N. Pastushok、Krzysztof E. Krakowiak、N. Kent Dalley、Xian Xin Zhang、Reed M. Izatt

  DOI：10.1021/jo980414z

  日期：1998.7.1

  A series of p-nitroanisole-containing tetraazacrown (14-18), diazacryptand (22), and diazadithia-crown (23-25) macrocycles has been prepared by treating the appropriate secondary diamine, diazacrown, or dimercaptan with 2,6-bis[(2 -chloroacetamido)methyl]-4-nitroanisole (BB). Five of these p-nitroanisole-containing macrocycles were reported earlier. Four new bis(p-nitroanisole)-containing macrocycles resulting from a 2 + 2 macrocyclization of diamine or dimercaptan with BE were also isolated. Six of the p-nitroanisole-containing macrocycles (16, 17, 22-25) were converted to the p-nitrophenol-containing macrocycles (27-32) on treatment with LiI in refluxing pyridine. Thermodynamic quantities (log K, Delta H, and T Delta S) for the interactions of four new compounds (24, 27, 31, and 32) with Na+, K+, Ba2+, Ag+, and Pb2+ were evaluated by calorimetric titration at 25.0 degrees C in either 70% or absolute methanol solution. The compounds show strong interactions with Ag+ and Pb2+ but very weak interactions with Na+, K+, and Ba2+. Ligand 31 exhibited high selectivity for Ag+ over Pb2+. X-ray crystal structures were obtained for diazadithia macrocycle 23 and the Ag+-31 complex.