1,3,5-tris(2-N-methylaminoethoxy)benzene | 784213-08-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 1,3,5-tris(2-N-methylaminoethoxy)benzene
• CAS: 784213-08-7
• 化学式: C₁₅H₂₇N₃O₃
• 分子量: 297.398
• InChiKey: DZYSNNWXSVIYAT-UHFFFAOYSA-N

物化性质

• 沸点：
  435.3±45.0 °C(predicted)
• 密度：
  1.036±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.48
• 重原子数：
  21.0
• 可旋转键数：
  12.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  63.78
• 氢给体数：
  3.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  β-D-galactopyranosyl-(1->4)-β-D-glucopyranosyl-(1->6)-D-galactopyranose 、 1,3,5-tris(2-N-methylaminoethoxy)benzene 在 sodium cyanoborohydride 、 溶剂黄146 作用下， 以 various solvent(s) 为溶剂， 反应 168.0h， 以93%的产率得到(2S,3R,4S,5R)-1-[2-[3,5-bis[2-[[(2S,3R,4S,5R)-6-[(2R,3R,4R,5S,6R)-3,4-dihydroxy-6-(hydroxymethyl)-5-[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-2,3,4,5-tetrahydroxyhexyl]-methylamino]ethoxy]phenoxy]ethyl-methylamino]-6-[(2R,3R,4R,5S,6R)-3,4-dihydroxy-6-(hydroxymethyl)-5-[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxyhexane-2,3,4,5-tetrol
  参考文献：
  名称：

  A Self-Assembled Multivalent Pseudopolyrotaxane for Binding Galectin-1

  摘要：

  A self-assembled pseudopolyrotaxane consisting of lactoside-displaying cyclodextrin (CD) "beads" threaded onto a linear polyviologen "string" was investigated for its ability to inhibit galectin-1-mediated T-cell agglutination. The CDs of the pseudopolyrotaxane are able to spin around the axis of the polymer chain as well as to move back and forth along its backbone to alter the presentation of its ligand. This supramolecular superstructure incorporates all the advantages of polymeric structures, such as the ability to span large distances, along with a distinctively dynamic presentation of its lactoside ligands to afford a neoglycoconjugate that can adjust to the relative stereochemistries of the lectin's binding sites. The pseudopolyrotaxane exhibited a valency-corrected 10-fold enhancement over native lactose in the agglutination assay, which was greater than the enhancements observed for lactoside-bearing trivalent glycoclusters and a lactoside-bearing chitosan polymer tested using the same assay. The experimental results indicate that supramolecular architectures, such as the pseudo polyrotaxane, provide tools for investigating protein-carbohydrate interactions.

  DOI：

  10.1021/ja0491073
• 作为产物：
  描述：

  2,2',2''-(benzene-1,3,5-triyltris(oxy))tris(ethan-1-ol) 在 palladium on activated charcoal 氢气 、 potassium carbonate 作用下， 以 四氢呋喃 、 吡啶 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 48.0h， 生成 1,3,5-tris(2-N-methylaminoethoxy)benzene
  参考文献：
  名称：

  A Self-Assembled Multivalent Pseudopolyrotaxane for Binding Galectin-1

  摘要：

  A self-assembled pseudopolyrotaxane consisting of lactoside-displaying cyclodextrin (CD) "beads" threaded onto a linear polyviologen "string" was investigated for its ability to inhibit galectin-1-mediated T-cell agglutination. The CDs of the pseudopolyrotaxane are able to spin around the axis of the polymer chain as well as to move back and forth along its backbone to alter the presentation of its ligand. This supramolecular superstructure incorporates all the advantages of polymeric structures, such as the ability to span large distances, along with a distinctively dynamic presentation of its lactoside ligands to afford a neoglycoconjugate that can adjust to the relative stereochemistries of the lectin's binding sites. The pseudopolyrotaxane exhibited a valency-corrected 10-fold enhancement over native lactose in the agglutination assay, which was greater than the enhancements observed for lactoside-bearing trivalent glycoclusters and a lactoside-bearing chitosan polymer tested using the same assay. The experimental results indicate that supramolecular architectures, such as the pseudo polyrotaxane, provide tools for investigating protein-carbohydrate interactions.

  DOI：

  10.1021/ja0491073