4,13-bis[12-[13-(4-nitrobenzyl)-4,13-diaza-18-crown-6-4-yl]dodecyl]-4,13-diaza-18-crown-6 | 179084-81-2

• 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: 4,13-bis[12-[13-(4-nitrobenzyl)-4,13-diaza-18-crown-6-4-yl]dodecyl]-4,13-diaza-18-crown-6
• 英文别名: 7,16-Bis[12-[16-[(4-nitrophenyl)methyl]-1,4,10,13-tetraoxa-7,16-diazacyclooctadec-7-yl]dodecyl]-1,4,10,13-tetraoxa-7,16-diazacyclooctadecane；7,16-bis[12-[16-[(4-nitrophenyl)methyl]-1,4,10,13-tetraoxa-7,16-diazacyclooctadec-7-yl]dodecyl]-1,4,10,13-tetraoxa-7,16-diazacyclooctadecane
• CAS: 179084-81-2
• 化学式: C₇₄H₁₃₂N₈O₁₆
• 分子量: 1389.91
• InChiKey: YYGQAOWDJRBRAU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10
• 重原子数：
  98
• 可旋转键数：
  30
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.84
• 拓扑面积：
  222
• 氢给体数：
  0
• 氢受体数：
  22

反应信息

• 作为产物：
  描述：

  二氮杂18-冠醚-6 在 丁腈 、 sodium carbonate 、 potassium iodide 作用下， 反应 12.0h， 生成 4,13-bis[12-[13-(4-nitrobenzyl)-4,13-diaza-18-crown-6-4-yl]dodecyl]-4,13-diaza-18-crown-6
  参考文献：
  名称：

  Synthetic Transmembrane Channels:  Functional Characterization Using Solubility Calculations, Transport Studies, and Substituent Effects

  摘要：

  Dibenzyldiaza-18-crown-6 (PhCH2[N18N]CH2Ph, 1), di(dodecyldiaza-18-crown-6 (C12H25[N18N]C12H25, 2), HOOC(CH2)(11)[N18N](CH2)(11)COOH (3), (18N)(CH2)(12)[N18N](CH2)(12)[N18] (4), [N18N](CH2)(12)[N18N](CH2)(12)[N18N] (5), C12H25[N18N](CH2)(12)[N18N](CH2)(12)[N18N]C12H25 (6), PhCH2[N18N](CH2)(12)[N18N](CH2)(12)[N18N]CH2Ph (7), 4-(p-MeOC6H4CH2[N18N]C-12)(2)[N18N] (8), (p-NO2C6H4CH2[N18N]C-12)(2)[N18N] (9), and [chol-O-(CH2)(2)[N18N]C-12](2)[N18N] (10) were studied. Octanol-water partition coefficients were determined for 1, 6, 7, 8, 10, and 3-cholestanyl-OCOCH2[N18N](CH2)(12)[N18N](CH2)(12)[N18N]COCH2O-3-cholestanyl (11). All were found to favor octanol, and by implication the phospholipid bilayer membrane, by at least 10(4)-fold. Transport of Na+ was assessed in both a phospholipid bilayer and in a bulk CHCl3 membrane phase. Addition of ionophores to the latter was found in some cases to strongly enhance CHCl3 phase hydration. An attempt to correlate transport rates determined in the two systems failed, suggesting that the carrier mechanism, required in the CHCl3 phase, does not apply to the tris(macrocyclic) compounds in the bilayer. Sodium transport rates were also assessed for these compounds by using the bilayer clamp technique. Although Na+ flux rates thus determined for 7-9 in the phospholipid bilayer did not correlate with results obtained by the Na-23-NMR technique, the traces are similar to those obtained with protein channels, further supporting the function of tris(macrocycle)s as channel formers.

  DOI：

  10.1021/ja962694a

文献信息

• Synthetic Transmembrane Channels:  Functional Characterization Using Solubility Calculations, Transport Studies, and Substituent Effects
  作者：Oscar Murillo、Iwao Suzuki、Ernesto Abel、Clare L. Murray、Eric S. Meadows、Takashi Jin、George W. Gokel

  DOI：10.1021/ja962694a

  日期：1997.6.1

  Dibenzyldiaza-18-crown-6 (PhCH2[N18N]CH2Ph, 1), di(dodecyldiaza-18-crown-6 (C12H25[N18N]C12H25, 2), HOOC(CH2)(11)[N18N](CH2)(11)COOH (3), (18N)(CH2)(12)[N18N](CH2)(12)[N18] (4), [N18N](CH2)(12)[N18N](CH2)(12)[N18N] (5), C12H25[N18N](CH2)(12)[N18N](CH2)(12)[N18N]C12H25 (6), PhCH2[N18N](CH2)(12)[N18N](CH2)(12)[N18N]CH2Ph (7), 4-(p-MeOC6H4CH2[N18N]C-12)(2)[N18N] (8), (p-NO2C6H4CH2[N18N]C-12)(2)[N18N] (9), and [chol-O-(CH2)(2)[N18N]C-12](2)[N18N] (10) were studied. Octanol-water partition coefficients were determined for 1, 6, 7, 8, 10, and 3-cholestanyl-OCOCH2[N18N](CH2)(12)[N18N](CH2)(12)[N18N]COCH2O-3-cholestanyl (11). All were found to favor octanol, and by implication the phospholipid bilayer membrane, by at least 10(4)-fold. Transport of Na+ was assessed in both a phospholipid bilayer and in a bulk CHCl3 membrane phase. Addition of ionophores to the latter was found in some cases to strongly enhance CHCl3 phase hydration. An attempt to correlate transport rates determined in the two systems failed, suggesting that the carrier mechanism, required in the CHCl3 phase, does not apply to the tris(macrocyclic) compounds in the bilayer. Sodium transport rates were also assessed for these compounds by using the bilayer clamp technique. Although Na+ flux rates thus determined for 7-9 in the phospholipid bilayer did not correlate with results obtained by the Na-23-NMR technique, the traces are similar to those obtained with protein channels, further supporting the function of tris(macrocycle)s as channel formers.