N1,N3-dihexyl-5-iodoisophthalamide | 1262899-03-5

• 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: N1,N3-dihexyl-5-iodoisophthalamide
• 英文别名: 1-N,3-N-dihexyl-5-iodobenzene-1,3-dicarboxamide
• CAS: 1262899-03-5
• 化学式: C₂₀H₃₁IN₂O₂
• 分子量: 458.383
• InChiKey: PMPJAHASAFFBCV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  25
• 可旋转键数：
  12
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  58.2
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  ferrocene boronic acid 、 N1,N3-dihexyl-5-iodoisophthalamide 在 (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride 作用下， 以 sodium hydroxide 、 乙二醇二甲醚 为溶剂， 以59%的产率得到N1,N3-dihexyl-5-ferrocenylisophthalamide
  参考文献：
  名称：

  A ferrocene functionalized rotaxanehost system capable of the electrochemical recognition of chloride

  摘要：

  通过氯阴离子模板化和闭环偏析法制备了一种二茂铁附加的轮烷。去除氯模板后，通过 1H NMR 光谱和电化学实验证明，这种轮烷对氯离子具有选择性，而对碱性较强的氧阴离子则没有选择性，这与无环类似物形成了明显的对比--这是第一个基于溶液的氧化还原活性互锁主系统的例子，该系统能够通过电化学识别阴离子。

  DOI：

  10.1039/c0ob00458h
• 作为产物：
  描述：

  正己胺 、 5-iodoisophthaloyl dichloride 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 16.0h， 以1.44 g的产率得到N1,N3-dihexyl-5-iodoisophthalamide
  参考文献：
  名称：

  A ferrocene functionalized rotaxanehost system capable of the electrochemical recognition of chloride

  摘要：

  通过氯阴离子模板化和闭环偏析法制备了一种二茂铁附加的轮烷。去除氯模板后，通过 1H NMR 光谱和电化学实验证明，这种轮烷对氯离子具有选择性，而对碱性较强的氧阴离子则没有选择性，这与无环类似物形成了明显的对比--这是第一个基于溶液的氧化还原活性互锁主系统的例子，该系统能够通过电化学识别阴离子。

  DOI：

  10.1039/c0ob00458h

文献信息

• A Halogen‐Bond‐Driven Artificial Chloride‐Selective Channel Constructed from 5‐Iodoisophthalamide‐based Molecules
  作者：Rashmi Sharma、Susmita Sarkar、Sandip Chattopadhayay、Jagannath Mondal、Pinaki Talukdar

  DOI：10.1002/anie.202319919

  日期：2024.5.6

  Despite considerable emphasis on advancing artificial ion channels, progress is constrained by the limited availability of small molecules with the necessary attributes of self‐assembly and ion selectivity. In this study, a library of small molecules based on 5‐haloisophthalamide and a non‐halogenated isophthalamide were examined for their ion transport properties across the lipid bilayer membranes, and the finding demonstrates that the di‐hexyl‐substituted 5‐iodoisophthalamide derivative exhibits the highest level of activity. Furthermore, it was established that the highest active compound facilitates the selective chloride transport that occurs via an antiport‐mediated mechanism. The crystal structure of the compound unveils a distinctive self‐assembly of molecules, forming a zig‐zag channel pore that is well‐suited for the permeation of anions. Planar bilayer conductance measurements proved the formation of chloride selective channels. A molecular dynamics simulation study, relying on the self‐assembled component derived from the crystal structure, affirmed the paramount significance of intermolecular hydrogen bonding in the formation of supramolecular barrel‐rosette structures that span the bilayer. Furthermore, it was demonstrated that the transport of chloride across the lipid bilayer membrane is facilitated by the synergistic effects of halogen bonding and hydrogen bonding within the channel.