4-Triphenylgermylphenol | 1261245-93-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 4-Triphenylgermylphenol
• 英文别名: 4-triphenylgermylphenol
• CAS: 1261245-93-5
• 化学式: C₂₄H₂₀GeO
• 分子量: 397.012
• InChiKey: QFDXAFGZBMGESH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.77
• 重原子数：
  26
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  4-溴苯酚 、 三苯基氯化锗 在 正丁基锂 作用下， 以 四氢呋喃 、 正戊烷 为溶剂， 反应 5.5h， 以54%的产率得到4-Triphenylgermylphenol
  参考文献：
  名称：

  Increased Hydrophobicity and Estrogenic Activity of Simple Phenols with Silicon and Germanium-Containing Substituents

  摘要：

  Here, we report the systematic synthesis and characterization of simple phenols bearing a trialkyl(aryl)silyl or trialkyl(aryl)germyl functional group as a hydrophobic substituent. These silicon and germanium analogues exhibited higher hydrophobicity than the corresponding carbon analogues, with a difference in log P value of approximately 0.6, independent of the alkyl(aryl) species. Trimethylsilylphenol and trimethylgermylphenol exhibited smaller pK(a) values than the corresponding carbon analogue or unsubstituted phenol, indicating that trialkylsilyl and trialkylgermyl functional groups have a negative substituent constant (sigma). The trialkylsilyl- and trialkylgermylphenols exhibited more potent estrogenic activity as compared with the carbon analogues. The substituent parameters and structure-activity relationship reported here may be helpful for drug discovery utilizing the heavier group 14 elements.

  DOI：

  10.1021/jm3013757

文献信息

• Increased Hydrophobicity and Estrogenic Activity of Simple Phenols with Silicon and Germanium-Containing Substituents
  作者：Shinya Fujii、Yu Miyajima、Hiroyuki Masuno、Hiroyuki Kagechika

  DOI：10.1021/jm3013757

  日期：2013.1.10

  Here, we report the systematic synthesis and characterization of simple phenols bearing a trialkyl(aryl)silyl or trialkyl(aryl)germyl functional group as a hydrophobic substituent. These silicon and germanium analogues exhibited higher hydrophobicity than the corresponding carbon analogues, with a difference in log P value of approximately 0.6, independent of the alkyl(aryl) species. Trimethylsilylphenol and trimethylgermylphenol exhibited smaller pK(a) values than the corresponding carbon analogue or unsubstituted phenol, indicating that trialkylsilyl and trialkylgermyl functional groups have a negative substituent constant (sigma). The trialkylsilyl- and trialkylgermylphenols exhibited more potent estrogenic activity as compared with the carbon analogues. The substituent parameters and structure-activity relationship reported here may be helpful for drug discovery utilizing the heavier group 14 elements.