bis[8-(4-tert-butoxycarbonylamidobenzoyl)octyl] 5-hydroxyisophthalate | 501088-86-4

• 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: bis[8-(4-tert-butoxycarbonylamidobenzoyl)octyl] 5-hydroxyisophthalate
• 英文别名: Bis[8-[4-[(2-methylpropan-2-yl)oxycarbonylamino]benzoyl]oxyoctyl] 5-hydroxybenzene-1,3-dicarboxylate
• CAS: 501088-86-4
• 化学式: C₄₈H₆₄N₂O₁₃
• 分子量: 877.042
• InChiKey: HHPKUKFJAUORTK-UHFFFAOYSA-N

物化性质

• 沸点：
  857.4±65.0 °C(Predicted)
• 密度：
  1.189±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  10.5
• 重原子数：
  63
• 可旋转键数：
  32
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  202
• 氢给体数：
  3
• 氢受体数：
  13

反应信息

• 作为反应物：
  描述：

  对苯二甲酰氯 、 bis[8-(4-tert-butoxycarbonylamidobenzoyl)octyl] 5-hydroxyisophthalate 在 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 12.0h， 以75%的产率得到bis(3,5-bis[8-(4-tert-butoxycarbonylamidobenzoyl)octyl]carboxyphenyl) terephthalate
  参考文献：
  名称：

  Ion Channels from Linear and Branched Bola-Amphiphiles

  摘要：

  The synthesis and characterization of the ion channel activity of three new bola-amphiphiles is described. These compounds are conceptually derived from a previously reported bis-cyclophane bola-amphiphile through opening of the cyclophanes to acyclic structures and were found to readily form ion channels in planar bilayer membranes as assessed by bilayer clamp single-channel analysis. All three compounds behaved very similarly: the dominant channels formed by all three are Ohmic with specific conductance of 10 +/- 1 pS (NaCl electrolyte) and 39 +/- 1 pS (CsCl electrolyte). Singleion permeability ratios, determined from dissymmetric electrolyte experiments, showed the selectivity P(Cs+) > P(Na+) > P(Cl-). Less frequently, lower conductance channels were also observed to act independently of the dominant channels. The lifetimes of the dominant channels range from 70 to 280 ms for the three compounds with some very long-lived openings (20-40 s) observed for two of the three. The lower conductance states have shorter lifetimes. This study demonstrates that bis-macrocyclic compounds are not essential for channel formation by bola-amphiphiles, and opens a new class of channel-forming compounds for structure- activity optimization.

  DOI：

  10.1021/jo026415f
• 作为产物：
  描述：

  5-苄氧基异邻苯二甲酸 在 palladium on activated charcoal 磺酰氯 、 氢气 、 三乙胺 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 90.0 ℃ 、413.7 kPa 条件下， 反应 32.0h， 生成 bis[8-(4-tert-butoxycarbonylamidobenzoyl)octyl] 5-hydroxyisophthalate
  参考文献：
  名称：

  Ion Channels from Linear and Branched Bola-Amphiphiles

  摘要：

  The synthesis and characterization of the ion channel activity of three new bola-amphiphiles is described. These compounds are conceptually derived from a previously reported bis-cyclophane bola-amphiphile through opening of the cyclophanes to acyclic structures and were found to readily form ion channels in planar bilayer membranes as assessed by bilayer clamp single-channel analysis. All three compounds behaved very similarly: the dominant channels formed by all three are Ohmic with specific conductance of 10 +/- 1 pS (NaCl electrolyte) and 39 +/- 1 pS (CsCl electrolyte). Singleion permeability ratios, determined from dissymmetric electrolyte experiments, showed the selectivity P(Cs+) > P(Na+) > P(Cl-). Less frequently, lower conductance channels were also observed to act independently of the dominant channels. The lifetimes of the dominant channels range from 70 to 280 ms for the three compounds with some very long-lived openings (20-40 s) observed for two of the three. The lower conductance states have shorter lifetimes. This study demonstrates that bis-macrocyclic compounds are not essential for channel formation by bola-amphiphiles, and opens a new class of channel-forming compounds for structure- activity optimization.

  DOI：

  10.1021/jo026415f