1-{4,4-bis[4-(4-methoxycarbonylbenzyloxy)phenyl]piperidin-1-yl}ethanone | 425364-79-0

• 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: 1-{4,4-bis[4-(4-methoxycarbonylbenzyloxy)phenyl]piperidin-1-yl}ethanone
• 英文别名: Methyl 4-[[4-[1-acetyl-4-[4-[(4-methoxycarbonylphenyl)methoxy]phenyl]piperidin-4-yl]phenoxy]methyl]benzoate
• CAS: 425364-79-0
• 化学式: C₃₇H₃₇NO₇
• 分子量: 607.703
• InChiKey: MPOKXYFJTDNBMD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.3
• 重原子数：
  45
• 可旋转键数：
  12
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  91.4
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  1-{4,4-bis[4-(4-methoxycarbonylbenzyloxy)phenyl]piperidin-1-yl}ethanone 在 sodium tetrahydroborate 、 草酰氯 、 二甲基亚砜 、 lithium chloride 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 为溶剂， 反应 24.25h， 生成 1-{4,4-bis[4-(4-formylbenzyloxy)phenyl]piperidin-1-yl}ethanone
  参考文献：
  名称：

  Investigation of Synthetic Hosts That Model Cation-π Sites Found at Protein Binding Domains

  摘要：

  Small cyclophanes containing aromatic groups and dialkyl ammonium ions were created as model systems of the cation-pi complexes found at some protein binding domains. The hosts had different shapes in order to investigate the effect the arrangement of ammonium ions to aromatic surfaces has on their reactivity. pK(a) values of the hosts were substantially different in DMSO or (95/5) DMSO/D2O solutions, which showed that the ions existed in different environments of the hosts. Electrostatic charges, as determined by density functional calculations, revealed that the magnitude of a cationic charge depends on its position relative to an aromatic ring. Association constants of the hosts bound to the sodium salt of N-acetyl phenylalanine in d(6)-DMSO and in (95/5) d(6)-DMSO/D2O solutions were inversely proportional to the magnitude of the hosts' acidity constants. These results suggest that the magnitude of the positive charge for cationic groups of cation-pi complexes is reduced by being associated with electron-rich faces of aromatic rings. The aromatic rings, however, lessen the desolvation penalty that must be overcome for ligand binding, giving an overall more favorable association.

  DOI：

  10.1021/jo011124c
• 作为产物：
  描述：

  4-溴甲基苯甲酸甲酯 、 1-(4,4-bis(4-hydroxyphenyl)piperidin-1-yl)ethanone 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 以94%的产率得到1-{4,4-bis[4-(4-methoxycarbonylbenzyloxy)phenyl]piperidin-1-yl}ethanone
  参考文献：
  名称：

  Investigation of Synthetic Hosts That Model Cation-π Sites Found at Protein Binding Domains

  摘要：

  Small cyclophanes containing aromatic groups and dialkyl ammonium ions were created as model systems of the cation-pi complexes found at some protein binding domains. The hosts had different shapes in order to investigate the effect the arrangement of ammonium ions to aromatic surfaces has on their reactivity. pK(a) values of the hosts were substantially different in DMSO or (95/5) DMSO/D2O solutions, which showed that the ions existed in different environments of the hosts. Electrostatic charges, as determined by density functional calculations, revealed that the magnitude of a cationic charge depends on its position relative to an aromatic ring. Association constants of the hosts bound to the sodium salt of N-acetyl phenylalanine in d(6)-DMSO and in (95/5) d(6)-DMSO/D2O solutions were inversely proportional to the magnitude of the hosts' acidity constants. These results suggest that the magnitude of the positive charge for cationic groups of cation-pi complexes is reduced by being associated with electron-rich faces of aromatic rings. The aromatic rings, however, lessen the desolvation penalty that must be overcome for ligand binding, giving an overall more favorable association.

  DOI：

  10.1021/jo011124c

文献信息

• Investigation of Synthetic Hosts That Model Cation-π Sites Found at Protein Binding Domains
  作者：Vadims Dvornikovs、David B. Smithrud

  DOI：10.1021/jo011124c

  日期：2002.4.1

  Small cyclophanes containing aromatic groups and dialkyl ammonium ions were created as model systems of the cation-pi complexes found at some protein binding domains. The hosts had different shapes in order to investigate the effect the arrangement of ammonium ions to aromatic surfaces has on their reactivity. pK(a) values of the hosts were substantially different in DMSO or (95/5) DMSO/D2O solutions, which showed that the ions existed in different environments of the hosts. Electrostatic charges, as determined by density functional calculations, revealed that the magnitude of a cationic charge depends on its position relative to an aromatic ring. Association constants of the hosts bound to the sodium salt of N-acetyl phenylalanine in d(6)-DMSO and in (95/5) d(6)-DMSO/D2O solutions were inversely proportional to the magnitude of the hosts' acidity constants. These results suggest that the magnitude of the positive charge for cationic groups of cation-pi complexes is reduced by being associated with electron-rich faces of aromatic rings. The aromatic rings, however, lessen the desolvation penalty that must be overcome for ligand binding, giving an overall more favorable association.