1-N,3-N-bis(4-amino-2,5-dioctoxyphenyl)-2-methoxybenzene-1,3-dicarboxamide | 935510-50-2

• 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: 1-N,3-N-bis(4-amino-2,5-dioctoxyphenyl)-2-methoxybenzene-1,3-dicarboxamide
• CAS: 935510-50-2
• 化学式: C₅₃H₈₄N₄O₇
• 分子量: 889.273
• InChiKey: AXBKTZQBTMYJEA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  15.8
• 重原子数：
  64
• 可旋转键数：
  37
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  156
• 氢给体数：
  4
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  1-N,3-N-bis(4-amino-2,5-dioctoxyphenyl)-2-methoxybenzene-1,3-dicarboxamide 、 2-Pentyloxy-5-[(1Z,4Z,9Z,15Z)-10,15,20-tris-(3,5-di-tert-butyl-phenyl)-porphyrin-5-yl]-benzoic acid 在 4-二甲氨基吡啶 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 12.0h， 以46%的产率得到
  参考文献：
  名称：

  Dynamic [2]Catenanes Based on a Hydrogen Bonding-Mediated Bis-Zinc Porphyrin Foldamer Tweezer:  A Case Study

  摘要：

  This paper describes the self-assembly of a new class of three-component dynamic [2]catenanes, which are driven or stabilized by intramolecular hydrogen bonding, coordination, and electrostatic interaction. One of the component molecules 2, consisting of an aromatic oligoamide spacer and two peripheral zinc porphyrin units, was designed to adopt a folded preorganized conformation, which is stabilized by consecutive intramolecular three-centered hydrogen bonds. Component molecule 3 is a linear secondary ammonium bearing two peripheral pyridine units, which was designed to form a 1:1 complex with 24-crown-8 (5). The H-1 NMR and UV-vis experiments in CDCl3-CD3CN (4:1 v/v) revealed that, due to the preorganized U-shaped feature, 2 could efficiently bind 3 through the cooperative zinc-pyridine coordination to generate highly stable 1:1 complex 2 center dot 3. Adding 5 to the 1:1 solution of 2 and 3 led to the formation of dynamic three-component [2]catenane 2 center dot 3 center dot 5 as a result of the threading of 3 through 5. H-1 NMR studies indicated that in the 1:1:1 solution (3 mM) [2]catenane 2 center dot 3 center dot 5 was generated in 55% yield at 25 degrees C. The yield was increased with the reduction of the temperature and [2]catenane could be produced quantitatively in a 1:1:2 solution ([2] = 3 mM) at -13 degrees C. Replacing 3 with 1,2-bis(4,4'-bipyridinium)ethane (4) in the three-component solution could also give rise to similar dynamic [2]catenane 2 center dot 4 center dot 5 albeit in slightly lower yield.

  DOI：

  10.1021/jo062523g
• 作为产物：
  描述：

  对苯二酚 在 palladium on activated charcoal 氢气 、 硝酸 、 potassium carbonate 、 1-羟基苯并三唑 、 溶剂黄146 、 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 20.0~100.0 ℃ 、101.33 kPa 条件下， 反应 21.0h， 生成 1-N,3-N-bis(4-amino-2,5-dioctoxyphenyl)-2-methoxybenzene-1,3-dicarboxamide
  参考文献：
  名称：

  Dynamic [2]Catenanes Based on a Hydrogen Bonding-Mediated Bis-Zinc Porphyrin Foldamer Tweezer:  A Case Study

  摘要：

  This paper describes the self-assembly of a new class of three-component dynamic [2]catenanes, which are driven or stabilized by intramolecular hydrogen bonding, coordination, and electrostatic interaction. One of the component molecules 2, consisting of an aromatic oligoamide spacer and two peripheral zinc porphyrin units, was designed to adopt a folded preorganized conformation, which is stabilized by consecutive intramolecular three-centered hydrogen bonds. Component molecule 3 is a linear secondary ammonium bearing two peripheral pyridine units, which was designed to form a 1:1 complex with 24-crown-8 (5). The H-1 NMR and UV-vis experiments in CDCl3-CD3CN (4:1 v/v) revealed that, due to the preorganized U-shaped feature, 2 could efficiently bind 3 through the cooperative zinc-pyridine coordination to generate highly stable 1:1 complex 2 center dot 3. Adding 5 to the 1:1 solution of 2 and 3 led to the formation of dynamic three-component [2]catenane 2 center dot 3 center dot 5 as a result of the threading of 3 through 5. H-1 NMR studies indicated that in the 1:1:1 solution (3 mM) [2]catenane 2 center dot 3 center dot 5 was generated in 55% yield at 25 degrees C. The yield was increased with the reduction of the temperature and [2]catenane could be produced quantitatively in a 1:1:2 solution ([2] = 3 mM) at -13 degrees C. Replacing 3 with 1,2-bis(4,4'-bipyridinium)ethane (4) in the three-component solution could also give rise to similar dynamic [2]catenane 2 center dot 4 center dot 5 albeit in slightly lower yield.

  DOI：

  10.1021/jo062523g