2-(2,4,6-Trimethoxy-phenyl)-[1,3]dioxan-5-ylamine | 642478-44-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 2-(2,4,6-Trimethoxy-phenyl)-[1,3]dioxan-5-ylamine
• 英文别名: 2-(2,4,6-Trimethoxyphenyl)-1,3-dioxan-5-amine；2-(2,4,6-trimethoxyphenyl)-1,3-dioxan-5-amine
• CAS: 642478-44-2
• 化学式: C₁₃H₁₉NO₅
• 分子量: 269.298
• InChiKey: IKNNEHXSXCURLI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  72.2
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2-(2,4,6-Trimethoxy-phenyl)-[1,3]dioxan-5-ylamine 、 [2-(2,2,2-trifluoroacetylamino)ethoxy]acetic acid 在 4-二甲氨基吡啶 、 N,N'-二环己基碳二亚胺 、 DPTS 作用下， 以 二氯甲烷 为溶剂， 以53%的产率得到2,2,2-trifluoro-N-(2-{[2-(2,4,6-trimethoxyphenyl)-[1,3]-5-dioxanylcarbamoyl]methoxy}ethyl)acetamide
  参考文献：
  名称：

  Stimuli-Responsive Supramolecular Assemblies of Linear-Dendritic Copolymers

  摘要：

  With the goal of developing a pH-responsive micelle system, linear-dendritic block copolymers comprising poly(ethylene oxide) and either a polylysine or polyester dendron were prepared and hydrophobic groups were attached to the dendrimer periphery by highly acid-sensitive cyclic acetals. These copolymers were designed to form stable micelles in aqueous solution at neutral pH but to disintegrate into unimers at mildly acidic pH following loss of the hydrophobic groups upon acetal hydrolysis. Micelle formation was demonstrated by encapsulation of the fluorescent probe Nile Red, and the micelle sizes were determined by dynamic light scattering. The structure of the dendrimer block, its generation, and the synthetic method for linking the acetal groups to its periphery all had an influence on the critical micelle concentration and the micelle size. The rate of hydrolysis of the acetals at the micelle core was measured for each system at pH 7.4 and pH 5, and it was found that all systems were stable at neutral pH but underwent significant hydrolysis at pH 5 over several hours. The rate of hydrolysis at pH 5 was dependent on the structure of the copolymer, most notably the hydrophobicity of the core-forming block. To demonstrate the potential of these systems for controlled release, the release of Nile Red as a "model payload" was examined. At pH 7.4, the fluorescence of micelle-encapsulated Nile Red was relatively constant, indicating it was retained in the micelle, while at pH 5, the fluorescence decreased, consistent with its release into the aqueous environment. The rate of release was strongly correlated with the rate of acetal hydrolysis and was therefore controlled by the chemical structure of the copolymer. The mechanism of Nile Red release was investigated by monitoring the change in size of the micelles over time at acidic pH. Dynamic light scattering measurement showed a size decrease over time, eventually reaching the size of a unimer, thus providing evidence for the proposed micelle disintegration.

  DOI：

  10.1021/ja0463738
• 作为产物：
  描述：

  在 potassium carbonate 作用下， 以 甲醇 为溶剂， 以79%的产率得到2-(2,4,6-Trimethoxy-phenyl)-[1,3]dioxan-5-ylamine
  参考文献：
  名称：

  A new approach towards acid sensitive copolymer micelles for drug delivery

  摘要：

  描述了一种新的胶束系统，能够在轻度酸性条件下选择性释放其内容物。

  DOI：

  10.1039/b304251k

文献信息

• Stimuli-Responsive Supramolecular Assemblies of Linear-Dendritic Copolymers
  作者：Elizabeth R. Gillies、Thomas B. Jonsson、Jean M. J. Fréchet

  DOI：10.1021/ja0463738

  日期：2004.9.1

  With the goal of developing a pH-responsive micelle system, linear-dendritic block copolymers comprising poly(ethylene oxide) and either a polylysine or polyester dendron were prepared and hydrophobic groups were attached to the dendrimer periphery by highly acid-sensitive cyclic acetals. These copolymers were designed to form stable micelles in aqueous solution at neutral pH but to disintegrate into unimers at mildly acidic pH following loss of the hydrophobic groups upon acetal hydrolysis. Micelle formation was demonstrated by encapsulation of the fluorescent probe Nile Red, and the micelle sizes were determined by dynamic light scattering. The structure of the dendrimer block, its generation, and the synthetic method for linking the acetal groups to its periphery all had an influence on the critical micelle concentration and the micelle size. The rate of hydrolysis of the acetals at the micelle core was measured for each system at pH 7.4 and pH 5, and it was found that all systems were stable at neutral pH but underwent significant hydrolysis at pH 5 over several hours. The rate of hydrolysis at pH 5 was dependent on the structure of the copolymer, most notably the hydrophobicity of the core-forming block. To demonstrate the potential of these systems for controlled release, the release of Nile Red as a "model payload" was examined. At pH 7.4, the fluorescence of micelle-encapsulated Nile Red was relatively constant, indicating it was retained in the micelle, while at pH 5, the fluorescence decreased, consistent with its release into the aqueous environment. The rate of release was strongly correlated with the rate of acetal hydrolysis and was therefore controlled by the chemical structure of the copolymer. The mechanism of Nile Red release was investigated by monitoring the change in size of the micelles over time at acidic pH. Dynamic light scattering measurement showed a size decrease over time, eventually reaching the size of a unimer, thus providing evidence for the proposed micelle disintegration.
• A new approach towards acid sensitive copolymer micelles for drug delivery
  作者：Elizabeth R. Gillies、Jean M. J. Fréchet

  DOI：10.1039/b304251k

  日期：——

  A new micellar system capable of selective release of its contents under mildly acidic conditions is described.

  描述了一种新的胶束系统，能够在轻度酸性条件下选择性释放其内容物。