2,5-Dioctoxybenzene-1,4-diamine | 935510-49-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 2,5-Dioctoxybenzene-1,4-diamine
• CAS: 935510-49-9
• 化学式: C₂₂H₄₀N₂O₂
• 分子量: 364.572
• InChiKey: CWIUQQIUGQUOOQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.3
• 重原子数：
  26
• 可旋转键数：
  16
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  70.5
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2,5-Dioctoxybenzene-1,4-diamine 、 2-甲氧基间苯二甲酸 在 1-羟基苯并三唑 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 12.0h， 以70%的产率得到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
• 作为产物：
  描述：

  对苯二酚 在 palladium on activated charcoal 氢气 、 硝酸 、 potassium carbonate 、 溶剂黄146 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 20.0~100.0 ℃ 、101.33 kPa 条件下， 反应 9.0h， 生成 2,5-Dioctoxybenzene-1,4-diamine
  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

文献信息

• Hydrogen bonded arylamide-linked cholesteryl dimesogenic liquid crystals: a study of the length and side chain effects
  作者：Gui-Tao Wang、Xin Zhao、Zhan-Ting Li

  DOI：10.1016/j.tet.2010.11.046

  日期：2011.1

  Dimesogenic compounds 1a-c, 2a-i, and 3, that are composed of a hydrogen bonding-induced straight arylamide spacer and two appended cholesterol groups, have been designed and synthesized. The backbones of the rigid spacers of 1a-c, 2a-i, and 3 contain one, three, and five benzene units, which bear two, six, and ten alkoxyl (methoxyl, n-octoxyl, or n-dodecoxyl) groups, respectively. The thermal and optical properties of the compounds are investigated by using the differential scanning calorimetry (DSC), polarizing optical microscopy (POM), and powder X-ray diffraction (PXRD) analysis. It is revealed that la c exhibit one or two liquid crystalline (LC) phases, 2a-i exhibit no, one or two LC phases, while 3 exhibits one LC phase in a wide temperature range. Generally, the more and longer alkoxyl chains facilitate the formation of the LC phases at low temperature. Notably, compound 2g, which bears two methoxyl and four dodecoxyl groups, displays a blue-red color change during both the heating and cooling cycle. The result illustrates that dimesogens with large rigid spacers can exhibit different LC phases when long aliphatic chains are appended to balance the strong stacking of the rigid backbones. (C) 2010 Elsevier Ltd. All rights reserved.
• Dynamic [2]Catenanes Based on a Hydrogen Bonding-Mediated Bis-Zinc Porphyrin Foldamer Tweezer:  A Case Study
  作者：Jing Wu、Fang、Wen-Ya Lu、Jun-Li Hou、Chuang Li、Zong-Quan Wu、Xi-Kui Jiang、Zhan-Ting Li、Yi-Hua Yu

  DOI：10.1021/jo062523g

  日期：2007.4.1

  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.