tert-butyl 2-(6-bromonaphthalen-2-yloxy)acetate | 1198771-82-2

• 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: tert-butyl 2-(6-bromonaphthalen-2-yloxy)acetate
• 英文别名: (6-Bromonaphthalen-2-yloxy)-acetic acid tert-butyl ester；tert-butyl 2-(6-bromonaphthalen-2-yl)oxyacetate
• CAS: 1198771-82-2
• 化学式: C₁₆H₁₇BrO₃
• 分子量: 337.213
• InChiKey: VDLRQXUQKPODIL-UHFFFAOYSA-N

物化性质

• 沸点：
  414.1±20.0 °C(Predicted)
• 密度：
  1.349±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  tert-butyl 2-(6-bromonaphthalen-2-yloxy)acetate 在 三氟乙酸 作用下， 以 氯仿 为溶剂， 反应 24.0h， 以92%的产率得到2-(6-bromonaphthalen-2-yloxy)acetic acid
  参考文献：
  名称：

  Self-Assembly Mechanism for a Naphthalene−Dipeptide Leading to Hydrogelation

  摘要：

  Suitably functionalized dipeptides have been shown to be effective hydrogelators. The design of the hydrogelators and the mechanism by which hydrogelation occurs are both currently not well understood. Here, we have utilized the hydrolysis of glucono-delta-lactone to gluconic acid as a means of adjusting the pH in a naphthalene-alanylvaline solution allowing the specific targeting of the final pH. In addition, this method allows the assembly process to be characterized. We show that assembly begins as charge is removed from the C-terminus of the dipeptide. The removal of charge allows lateral assembly of the molecules leading to pi-pi stacking (shown by CD) and beta-sheet formation (as shown by IR and X-ray fiber diffraction). This leads to the formation of fibrous structures. Electron microscopy reveals that thin fibers form initially, with low persistence length. Lateral association then occurs to give bundles of fibers with higher persistence length. This results in the initially weak hydrogel becoming stronger with time. The final mechanical properties of the hydrogels are very similar irrespective of the amount of GdL added; rather, the time taken to achieving the final gel is determined by the GdL concentration. However, differences are observed between the networks under strain, implying that the kinetics of assembly do impart different final materials' properties. Overall, this study provides detailed understanding of the assembly process that leads to hydrogelation.

  DOI：

  10.1021/la903694a
• 作为产物：
  描述：

  6-溴-2-萘酚 、 氯乙酸叔丁酯 在 potassium carbonate 作用下， 以 丙酮 为溶剂， 以79%的产率得到tert-butyl 2-(6-bromonaphthalen-2-yloxy)acetate
  参考文献：
  名称：

  Self-Assembly Mechanism for a Naphthalene−Dipeptide Leading to Hydrogelation

  摘要：

  Suitably functionalized dipeptides have been shown to be effective hydrogelators. The design of the hydrogelators and the mechanism by which hydrogelation occurs are both currently not well understood. Here, we have utilized the hydrolysis of glucono-delta-lactone to gluconic acid as a means of adjusting the pH in a naphthalene-alanylvaline solution allowing the specific targeting of the final pH. In addition, this method allows the assembly process to be characterized. We show that assembly begins as charge is removed from the C-terminus of the dipeptide. The removal of charge allows lateral assembly of the molecules leading to pi-pi stacking (shown by CD) and beta-sheet formation (as shown by IR and X-ray fiber diffraction). This leads to the formation of fibrous structures. Electron microscopy reveals that thin fibers form initially, with low persistence length. Lateral association then occurs to give bundles of fibers with higher persistence length. This results in the initially weak hydrogel becoming stronger with time. The final mechanical properties of the hydrogels are very similar irrespective of the amount of GdL added; rather, the time taken to achieving the final gel is determined by the GdL concentration. However, differences are observed between the networks under strain, implying that the kinetics of assembly do impart different final materials' properties. Overall, this study provides detailed understanding of the assembly process that leads to hydrogelation.

  DOI：

  10.1021/la903694a