3-bromo-5-aminobenzyl 2-[2-(2-methoxyethoxy)ethoxy]ethyl ether | 318261-53-9

• 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: 3-bromo-5-aminobenzyl 2-[2-(2-methoxyethoxy)ethoxy]ethyl ether
• 英文别名: 3-Bromo-5-[2-[2-(2-methoxyethoxy)ethoxy]ethoxymethyl]aniline；3-bromo-5-[2-[2-(2-methoxyethoxy)ethoxy]ethoxymethyl]aniline
• CAS: 318261-53-9
• 化学式: C₁₄H₂₂BrNO₄
• 分子量: 348.237
• InChiKey: UPDCWPPZKWKAFU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  20
• 可旋转键数：
  11
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  62.9
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3-bromo-5-aminobenzyl 2-[2-(2-methoxyethoxy)ethoxy]ethyl ether 在 tris(dibenzylideneacetone)dipalladium (0) copper(l) iodide 、 亚硝酸特丁酯 、 三氟化硼乙醚 、 四丁基氟化铵 、 水 、 potassium carbonate 、 三乙胺 、 三苯基膦 、 碘甲烷 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 54.01h， 生成 1-Ethynyl-3-{2-[2-(2-methoxy-ethoxy)-ethoxy]-ethoxymethyl}-5-(3-{2-[2-(2-methoxy-ethoxy)-ethoxy]-ethoxymethyl}-phenylethynyl)-benzene
  参考文献：
  名称：

  Solvophobically Driven π-Stacking of Phenylene Ethynylene Macrocycles and Oligomers

  摘要：

  Phenylene ethynylene macrocycles and oligomers with three different side-chain linking groups (ester, benzyl ether, and phenyl ether) were synthesized to investigate their tendency to undergo solvent induced pi -stacked organization. H-1 NMR, UV, and fluorescence spectroscopies were used to probe two types of pi -stacked supramolecular organizations: the intramolecular conformational ordering of the oligomers, and the intermolecular aggregation of the macrocycles. One important conclusion is that solvent can play a very dramatic role in modulating the strength of the interactions that drive the association of these ct-stacked structures. The other important conclusion is that in a given solvent, the nature of the side chain linking group strongly influences the pi -stacking propensities. It was found that macrocycles and oligomers with the ether side chain linking group were prone to adopt pi -stacked structures in a range of solvents, whereas the corresponding macrocycles with benzyl ether and phenyl ether side chain linking groups showed only limited ability to pi -stack, even in the most polar solvent examined (DMSO). In the interest of manipulating the helix-coil folding transition of phenylene ethynylene oligomers, a heterosequence consisting of monomers with ester and benzyl ether side chain linkages was synthesized. The folding transition of the heterooligomer was intermediate to that observed for the corresponding homooligomers, suggesting that the backbone sequence can be used to tune the stability of conformations that are based on pi -stacked organizations.

  DOI：

  10.1021/ja002129e
• 作为产物：
  描述：

  3-溴-5-硝基苯甲酸 在 sodium hydroxide 、 硼烷四氢呋喃络合物 、 五氯化磷 、 四丁基碘化铵 、 甲烷 、 一水合肼 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 、 氯仿 为溶剂， 反应 63.0h， 生成 3-bromo-5-aminobenzyl 2-[2-(2-methoxyethoxy)ethoxy]ethyl ether
  参考文献：
  名称：

  Solvophobically Driven π-Stacking of Phenylene Ethynylene Macrocycles and Oligomers

  摘要：

  Phenylene ethynylene macrocycles and oligomers with three different side-chain linking groups (ester, benzyl ether, and phenyl ether) were synthesized to investigate their tendency to undergo solvent induced pi -stacked organization. H-1 NMR, UV, and fluorescence spectroscopies were used to probe two types of pi -stacked supramolecular organizations: the intramolecular conformational ordering of the oligomers, and the intermolecular aggregation of the macrocycles. One important conclusion is that solvent can play a very dramatic role in modulating the strength of the interactions that drive the association of these ct-stacked structures. The other important conclusion is that in a given solvent, the nature of the side chain linking group strongly influences the pi -stacking propensities. It was found that macrocycles and oligomers with the ether side chain linking group were prone to adopt pi -stacked structures in a range of solvents, whereas the corresponding macrocycles with benzyl ether and phenyl ether side chain linking groups showed only limited ability to pi -stack, even in the most polar solvent examined (DMSO). In the interest of manipulating the helix-coil folding transition of phenylene ethynylene oligomers, a heterosequence consisting of monomers with ester and benzyl ether side chain linkages was synthesized. The folding transition of the heterooligomer was intermediate to that observed for the corresponding homooligomers, suggesting that the backbone sequence can be used to tune the stability of conformations that are based on pi -stacked organizations.

  DOI：

  10.1021/ja002129e

文献信息

• Solvophobically Driven π-Stacking of Phenylene Ethynylene Macrocycles and Oligomers
  作者：Shreyasi Lahiri、Julie L. Thompson、Jeffrey S. Moore

  DOI：10.1021/ja002129e

  日期：2000.11.22

  Phenylene ethynylene macrocycles and oligomers with three different side-chain linking groups (ester, benzyl ether, and phenyl ether) were synthesized to investigate their tendency to undergo solvent induced pi -stacked organization. H-1 NMR, UV, and fluorescence spectroscopies were used to probe two types of pi -stacked supramolecular organizations: the intramolecular conformational ordering of the oligomers, and the intermolecular aggregation of the macrocycles. One important conclusion is that solvent can play a very dramatic role in modulating the strength of the interactions that drive the association of these ct-stacked structures. The other important conclusion is that in a given solvent, the nature of the side chain linking group strongly influences the pi -stacking propensities. It was found that macrocycles and oligomers with the ether side chain linking group were prone to adopt pi -stacked structures in a range of solvents, whereas the corresponding macrocycles with benzyl ether and phenyl ether side chain linking groups showed only limited ability to pi -stack, even in the most polar solvent examined (DMSO). In the interest of manipulating the helix-coil folding transition of phenylene ethynylene oligomers, a heterosequence consisting of monomers with ester and benzyl ether side chain linkages was synthesized. The folding transition of the heterooligomer was intermediate to that observed for the corresponding homooligomers, suggesting that the backbone sequence can be used to tune the stability of conformations that are based on pi -stacked organizations.