7,16-bis(5-chloro-2-hydroxy-3-nitrobenzyl)-1,4,10,13-tetraoxa-7,16-diazacyclooctadecane

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 7,16-bis(5-chloro-2-hydroxy-3-nitrobenzyl)-1,4,10,13-tetraoxa-7,16-diazacyclooctadecane
• 英文别名: 4-Chloro-2-[[16-[(5-chloro-2-hydroxy-3-nitrophenyl)methyl]-1,4,10,13-tetraoxa-7,16-diazacyclooctadec-7-yl]methyl]-6-nitrophenol
• 化学式: C₂₆H₃₄Cl₂N₄O₁₀
• 分子量: 633.483
• InChiKey: UBAAZDQDFZBWAY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  42
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  176
• 氢给体数：
  2
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  7,16-bis(5-chloro-2-hydroxy-3-nitrobenzyl)-1,4,10,13-tetraoxa-7,16-diazacyclooctadecane 在 platinum(IV) oxide 氢气 作用下， 以 甲醇 为溶剂， 反应 5.0h， 以98%的产率得到7,16-bis(3-amino-5-chloro-2-hydroxybenzyl)-1,4,10,13-tetraoxa-7,16-diazacyclooctadecane
  参考文献：
  名称：

  Diaza-18-Crown-6 Ligands Containing Two Aminophenol Side Arms:  New Heterobinuclear Metal Ion Receptors

  摘要：

  Three diaza-18-crown-6 ligands substituted with two aminophenol side arms were synthesized as possible heterobinuclear metal ion receptors. Bis(p-aminophenol)-substituted diaza-18-crown-6 ligand (13) was prepared by treating the diazacrown with alpha-bromo-4-nitro-o-cresol in the presence of N,N-diisopropylethylamine followed by reduction of the nitro groups. Bis(o-aminophenol)substituted diaza-18-crown-6 ligands (11 and 12) were prepared in two steps by the aminomethylation of either an o-nitrophenol or o-(trifluoroacetamido)phenol followed by reduction of the nitro groups or hydrolysis of the trifluoroacetamide groups. All new bisphenol-armed diazacrown ligands were purified by ultrasonication in MeOH followed by filtration and drying. Interaction of the ligands with Na+, K+, Ag+, and Cu2+ was evaluated by a calorimetric titration technique at 25 degrees C in MeOH. The complexes of Ag+ and Cu2+ much more stable than those of Na+ and K+. Heterobinuclear complexes were observed for 11-Cu2+- Na+ and 12-Cu2+-Na+ but not for 13-Cu2+-Na+ or for 12-Cu2+-Ag+.

  DOI：

  10.1021/jo9816212
• 作为产物：
  描述：

  聚合甲醛 、 4-氯-2-硝基苯酚 、 二氮杂18-冠醚-6 以 苯 为溶剂， 反应 20.0h， 以41%的产率得到7,16-bis(5-chloro-2-hydroxy-3-nitrobenzyl)-1,4,10,13-tetraoxa-7,16-diazacyclooctadecane
  参考文献：
  名称：

  Diaza-18-Crown-6 Ligands Containing Two Aminophenol Side Arms:  New Heterobinuclear Metal Ion Receptors

  摘要：

  Three diaza-18-crown-6 ligands substituted with two aminophenol side arms were synthesized as possible heterobinuclear metal ion receptors. Bis(p-aminophenol)-substituted diaza-18-crown-6 ligand (13) was prepared by treating the diazacrown with alpha-bromo-4-nitro-o-cresol in the presence of N,N-diisopropylethylamine followed by reduction of the nitro groups. Bis(o-aminophenol)substituted diaza-18-crown-6 ligands (11 and 12) were prepared in two steps by the aminomethylation of either an o-nitrophenol or o-(trifluoroacetamido)phenol followed by reduction of the nitro groups or hydrolysis of the trifluoroacetamide groups. All new bisphenol-armed diazacrown ligands were purified by ultrasonication in MeOH followed by filtration and drying. Interaction of the ligands with Na+, K+, Ag+, and Cu2+ was evaluated by a calorimetric titration technique at 25 degrees C in MeOH. The complexes of Ag+ and Cu2+ much more stable than those of Na+ and K+. Heterobinuclear complexes were observed for 11-Cu2+- Na+ and 12-Cu2+-Na+ but not for 13-Cu2+-Na+ or for 12-Cu2+-Ag+.

  DOI：

  10.1021/jo9816212

文献信息

• Diaza-18-Crown-6 Ligands Containing Two Aminophenol Side Arms:  New Heterobinuclear Metal Ion Receptors
  作者：Ning Su、Jerald S. Bradshaw、Xian Xin Zhang、Paul B. Savage、Krzysztof E. Krakowiak、Reed M. Izatt

  DOI：10.1021/jo9816212

  日期：1999.5.1

  Three diaza-18-crown-6 ligands substituted with two aminophenol side arms were synthesized as possible heterobinuclear metal ion receptors. Bis(p-aminophenol)-substituted diaza-18-crown-6 ligand (13) was prepared by treating the diazacrown with alpha-bromo-4-nitro-o-cresol in the presence of N,N-diisopropylethylamine followed by reduction of the nitro groups. Bis(o-aminophenol)substituted diaza-18-crown-6 ligands (11 and 12) were prepared in two steps by the aminomethylation of either an o-nitrophenol or o-(trifluoroacetamido)phenol followed by reduction of the nitro groups or hydrolysis of the trifluoroacetamide groups. All new bisphenol-armed diazacrown ligands were purified by ultrasonication in MeOH followed by filtration and drying. Interaction of the ligands with Na+, K+, Ag+, and Cu2+ was evaluated by a calorimetric titration technique at 25 degrees C in MeOH. The complexes of Ag+ and Cu2+ much more stable than those of Na+ and K+. Heterobinuclear complexes were observed for 11-Cu2+- Na+ and 12-Cu2+-Na+ but not for 13-Cu2+-Na+ or for 12-Cu2+-Ag+.