5-methoxy-m-xylylene bisphosphonic acid tetramethyl ester | 367927-25-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 5-methoxy-m-xylylene bisphosphonic acid tetramethyl ester
• 英文别名: 1,3-Bis(dimethoxyphosphorylmethyl)-5-methoxybenzene
• CAS: 367927-25-1
• 化学式: C₁₃H₂₂O₇P₂
• 分子量: 352.261
• InChiKey: CLTYFUZWXAFDAI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  22
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  80.3
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  四丁基氢氧化铵 、 5-methoxy-m-xylylene bisphosphonic acid tetramethyl ester 以 水 为溶剂， 反应 168.0h， 以100%的产率得到
  参考文献：
  名称：

  Optimization of a Synthetic Arginine Receptor. Systematic Tuning of Noncovalent Interactions

  摘要：

  The simple arginine binder I could be optimized by strengthening pi -cation as well as electrostatic interactions. Electron-donating or -withdrawing substituents in the 5-position provide experimental evidence for T-cation interactions, because binding energies increase by up to 0.6 kcal/mol due to a single benzene - guanidinium interaction. Even more effective is the introduction of a third phosphonate functionality at the correct distance, so that the guanidinium cation is recognized by optimal electrostatic and hydrogen bond interactions. Monte Carlo simulations and NOESY experiments confirm the expected complex geometries. The optimized host molecule 8 binds arginine half an order of magnitude more efficiently than the parent molecule.

  DOI：

  10.1021/jo0156161
• 作为产物：
  描述：

  3,5-二甲基苯甲醚 在 偶氮二异丁腈 N-溴代丁二酰亚胺(NBS) 作用下， 以 四氯化碳 为溶剂， 反应 3.0h， 生成 5-methoxy-m-xylylene bisphosphonic acid tetramethyl ester
  参考文献：
  名称：

  Optimization of a Synthetic Arginine Receptor. Systematic Tuning of Noncovalent Interactions

  摘要：

  The simple arginine binder I could be optimized by strengthening pi -cation as well as electrostatic interactions. Electron-donating or -withdrawing substituents in the 5-position provide experimental evidence for T-cation interactions, because binding energies increase by up to 0.6 kcal/mol due to a single benzene - guanidinium interaction. Even more effective is the introduction of a third phosphonate functionality at the correct distance, so that the guanidinium cation is recognized by optimal electrostatic and hydrogen bond interactions. Monte Carlo simulations and NOESY experiments confirm the expected complex geometries. The optimized host molecule 8 binds arginine half an order of magnitude more efficiently than the parent molecule.

  DOI：

  10.1021/jo0156161

文献信息

• Optimization of a Synthetic Arginine Receptor. Systematic Tuning of Noncovalent Interactions
  作者：Stephan Rensing、Markus Arendt、Andreas Springer、Thomas Grawe、Thomas Schrader

  DOI：10.1021/jo0156161

  日期：2001.8.1

  The simple arginine binder I could be optimized by strengthening pi -cation as well as electrostatic interactions. Electron-donating or -withdrawing substituents in the 5-position provide experimental evidence for T-cation interactions, because binding energies increase by up to 0.6 kcal/mol due to a single benzene - guanidinium interaction. Even more effective is the introduction of a third phosphonate functionality at the correct distance, so that the guanidinium cation is recognized by optimal electrostatic and hydrogen bond interactions. Monte Carlo simulations and NOESY experiments confirm the expected complex geometries. The optimized host molecule 8 binds arginine half an order of magnitude more efficiently than the parent molecule.