8⁴,1⁴-dimethylsulfanyl-7³,6²,5³,4²,3³,2²-hexa(18-azacrown-6-N-carbonylmethoxy)-p-octiphenyl | 256387-82-3

• 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: 8⁴,1⁴-dimethylsulfanyl-7³,6²,5³,4²,3³,2²-hexa(18-azacrown-6-N-carbonylmethoxy)-p-octiphenyl
• 英文别名: 2-[2-(4-Methylsulfanylphenyl)-5-[4-[4-[4-[4-[4-(4-methylsulfanylphenyl)-3-[2-oxo-2-(1,4,7,10,13-pentaoxa-16-azacyclooctadec-16-yl)ethoxy]phenyl]-2-[2-oxo-2-(1,4,7,10,13-pentaoxa-16-azacyclooctadec-16-yl)ethoxy]phenyl]-3-[2-oxo-2-(1,4,7,10,13-pentaoxa-16-azacyclooctadec-16-yl)ethoxy]phenyl]-2-[2-oxo-2-(1,4,7,10,13-pentaoxa-16-azacyclooctadec-16-yl)ethoxy]phenyl]-3-[2-oxo-2-(1,4,7,10,13-pentaoxa-16-azacyclooctadec-16-yl)ethoxy]phenyl]phenoxy]-1-(1,4,7,10,13-pentaoxa-16-azacyclooctadec-16-yl)ethanone
• CAS: 256387-82-3
• 化学式: C₁₃₄H₁₈₈N₆O₄₂S₂
• 分子量: 2619.11
• InChiKey: ZIOSMPONVOUTPQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  184
• 可旋转键数：
  27
• 环数：
  14.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  505
• 氢给体数：
  0
• 氢受体数：
  44

反应信息

• 作为反应物：
  描述：

  8⁴,1⁴-dimethylsulfanyl-7³,6²,5³,4²,3³,2²-hexa(18-azacrown-6-N-carbonylmethoxy)-p-octiphenyl 在 Oxone 作用下， 以 四氢呋喃 、 甲醇 、 水 为溶剂， 反应 14.0h， 以50%的产率得到1⁴-methylsulfanyl-8⁴-methylsulfonyl-7³,6²,5³,4²,3³,2²-hexa(18-azacrown-6-N-carbonylmethoxy)-p-octiphenyl
  参考文献：
  名称：

  Synthesis of Multiply Substituted, Ion Channel Forming Octi(p-phenylene)s:  Theme and Variations

  摘要：

  [GRAPHICS]To facilitate the access to unique models for biological processes, we examined six different synthetic routes to octi(p-phenylene) rods with lateral and terminal substitutents R-L and R-T. This systematic study allowed us to increase to overall yield for the synthesis of a new class of oligo(p-phenylene) ionophores about 20 times and to provide general insights into the practicability of synthetic routes to multiply substituted molecular rods.

  DOI：

  10.1021/ol991210n
• 作为产物：
  描述：

  4-甲硫基苯硼酸 、 6⁴,1⁴-diiodo-6³,5²,4³,3²,2³,1³-hexa(18-azacrown-6-N-carbonylmethoxy)-p-sexiphenyl 在 四(三苯基膦)钯 、 sodium carbonate 作用下， 以 水 、 甲苯 为溶剂， 反应 18.0h， 以40%的产率得到8⁴,1⁴-dimethylsulfanyl-7³,6²,5³,4²,3³,2²-hexa(18-azacrown-6-N-carbonylmethoxy)-p-octiphenyl
  参考文献：
  名称：

  Synthesis of Multiply Substituted, Ion Channel Forming Octi(p-phenylene)s:  Theme and Variations

  摘要：

  [GRAPHICS]To facilitate the access to unique models for biological processes, we examined six different synthetic routes to octi(p-phenylene) rods with lateral and terminal substitutents R-L and R-T. This systematic study allowed us to increase to overall yield for the synthesis of a new class of oligo(p-phenylene) ionophores about 20 times and to provide general insights into the practicability of synthetic routes to multiply substituted molecular rods.

  DOI：

  10.1021/ol991210n

文献信息

• Electrostatics of Cell Membrane Recognition:  Structure and Activity of Neutral and Cationic Rigid Push-Pull Rods in Isoelectric, Anionic, and Polarized Lipid Bilayer Membranes
  作者：Naomi Sakai、David Gerard、Stefan Matile

  DOI：10.1021/ja003141+

  日期：2001.3.1

  uncharged rigid push-pull rods in polarized bilayers. The similarly increased activity of cationic rigid push-pull rods with an electrostatic asymmetry comparable to that of alpha-helical bee toxin melittin (positive charge near negative axial dipole terminus) is shown by fluorescence-depth quenching experiments to originate from the stabilization of transmembrane rod orientation by the membrane potential

  报告了不同轴向静电不对称的刚棒离子载体的设计、合成以及结构和功能研究。所采用的设计策略强调存在（a）刚性支架以最小化构象复杂性，（b）单分子离子传导途径以最小化超结构复杂性并监测功能，（c）扩展荧光团以监测结构，（d ) 可变轴向杆偶极子，和 (e) 可变终端电荷以产生轴向不对称。等电、阴离子和极化双层膜的研究证实了极化双层中不带电的刚性推拉杆的活性普遍增加。荧光深度淬灭实验表明，具有静电不对称性的阳离子刚性推拉杆的活性类似增加，其静电不对称性与 α-螺旋蜜蜂毒素蜂毒肽（负轴向偶极子末端附近的正电荷）相当，源于跨膜杆的稳定性通过膜电位定向。结构研究表明，具有与 α 螺旋天然抗生素（靠近正轴向偶极子末端的正电荷）相当的静电不对称性的刚性推拉杆的活性降低，其起源于膜电位可比的杆“喷射”在哺乳动物质膜中发现的。
• Synthesis of Multiply Substituted, Ion Channel Forming Octi(<i>p</i>-phenylene)s:  Theme and Variations
  作者：Fabien Robert、Jean-Yves Winum、Naomi Sakai、David Gerard、Stefan Matile

  DOI：10.1021/ol991210n

  日期：2000.1.1

  [GRAPHICS]To facilitate the access to unique models for biological processes, we examined six different synthetic routes to octi(p-phenylene) rods with lateral and terminal substitutents R-L and R-T. This systematic study allowed us to increase to overall yield for the synthesis of a new class of oligo(p-phenylene) ionophores about 20 times and to provide general insights into the practicability of synthetic routes to multiply substituted molecular rods.