3,5-bis[2-(2-{2-[2-(adamantan-1-yloxy)ethoxy]ethoxy}ethoxy)ethoxy]-4-methoxy-1-nitrobenzene | 1313583-18-4

• 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: 3,5-bis[2-(2-{2-[2-(adamantan-1-yloxy)ethoxy]ethoxy}ethoxy)ethoxy]-4-methoxy-1-nitrobenzene
• CAS: 1313583-18-4
• 化学式: C₄₃H₆₇NO₁₃
• 分子量: 806.004
• InChiKey: DLJSFTAFDKADRR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.43
• 重原子数：
  57.0
• 可旋转键数：
  30.0
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  144.67
• 氢给体数：
  0.0
• 氢受体数：
  13.0

反应信息

• 作为反应物：
  描述：

  3,5-bis[2-(2-{2-[2-(adamantan-1-yloxy)ethoxy]ethoxy}ethoxy)ethoxy]-4-methoxy-1-nitrobenzene 在 palladium 10% on activated carbon 、 氢气 作用下， 以 甲醇 为溶剂， 20.0 ℃ 、100.0 kPa 条件下， 反应 4.0h， 以93%的产率得到3,5-bis[2-(2-{2-[2-(adamantan-1-yloxy)ethoxy]ethoxy}ethoxy)ethoxy]-4-methoxyaniline
  参考文献：
  名称：

  Probing Multivalent Interactions in a Synthetic Host–Guest Complex by Dynamic Force Spectroscopy

  摘要：

  Multivalency is present in many biological and synthetic systems. Successful application of multivalency depends on a correct understanding of the thermodynamics and kinetics of this phenomenon. In this Article, we address the stability and strength of multivalent bonds with force spectroscopy techniques employing a synthetic adamantane/beta-cyclodextrin model system. Comparing the experimental findings to theoretical predictions for the rupture force and the kinetic off-rate, we find that when the valency of the complex is increased from mono- to di- to trivalent, there is a transition from quasi-equilibrium, with a constant rupture force of 99 pN, to a kinetically dependent state, with loading-rate-dependent rupture forces from 140 to 184 pN (divalent) and 175 to 210 pN (trivalent). Additional binding geometries, parallel monovalent ruptures, single-bound divalent ruptures, and single- and double-bound trivalent ruptures are identified. The experimental kinetic off-rates of the multivalent complexes show that the stability of the complexes is significantly enhanced with the number of bonds, in agreement with the predictions of a noncooperative multivalent model.

  DOI：

  10.1021/ja2016125
• 作为产物：
  描述：

  2-甲氧基间苯二酚 在 硝酸 、 silica gel 、 caesium carbonate 作用下， 以 二氯甲烷 、 丙酮 为溶剂， 反应 48.08h， 生成 3,5-bis[2-(2-{2-[2-(adamantan-1-yloxy)ethoxy]ethoxy}ethoxy)ethoxy]-4-methoxy-1-nitrobenzene
  参考文献：
  名称：

  Probing Multivalent Interactions in a Synthetic Host–Guest Complex by Dynamic Force Spectroscopy

  摘要：

  Multivalency is present in many biological and synthetic systems. Successful application of multivalency depends on a correct understanding of the thermodynamics and kinetics of this phenomenon. In this Article, we address the stability and strength of multivalent bonds with force spectroscopy techniques employing a synthetic adamantane/beta-cyclodextrin model system. Comparing the experimental findings to theoretical predictions for the rupture force and the kinetic off-rate, we find that when the valency of the complex is increased from mono- to di- to trivalent, there is a transition from quasi-equilibrium, with a constant rupture force of 99 pN, to a kinetically dependent state, with loading-rate-dependent rupture forces from 140 to 184 pN (divalent) and 175 to 210 pN (trivalent). Additional binding geometries, parallel monovalent ruptures, single-bound divalent ruptures, and single- and double-bound trivalent ruptures are identified. The experimental kinetic off-rates of the multivalent complexes show that the stability of the complexes is significantly enhanced with the number of bonds, in agreement with the predictions of a noncooperative multivalent model.

  DOI：

  10.1021/ja2016125