4-(benzylaminomethyl)thiophenol | 724452-17-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯硫酚类
• 英文名称: 4-(benzylaminomethyl)thiophenol
• 英文别名: 4-[(Benzylamino)methyl]benzenethiol
• CAS: 724452-17-9
• 化学式: C₁₄H₁₅NS
• 分子量: 229.346
• InChiKey: GRUXFRNAPFRPAW-UHFFFAOYSA-N

物化性质

• 沸点：
  364.4±22.0 °C(Predicted)
• 密度：
  1.122±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  13
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  六氟苯 、 4-(benzylaminomethyl)thiophenol 在 sodium hydride 作用下， 以 various solvent(s) 为溶剂， 反应 72.0h， 以58%的产率得到hexakis[4-(benzylaminomethyl)phenylthio]benzene
  参考文献：
  名称：

  Polyvalent Interactions in Unnatural Recognition Processes

  摘要：

  The synthesis of two cluster compounds, one containing six secondary dialkylammonium ion centers and the other possessing six benzo-m-phenylene[25]crown-8 (BMP25C8) macrocycles, both appended to hexakis(thiophenyl)benzene cores, is described. The binding of these clusters with complementary mono- and divalent ligands is investigated with NMR spectroscopy to probe polyvalency in these unnatural recognition systems. The ability of the two different families of clusters to bind complementary monovalent ligands is compared with that of the monovalent receptor pair, namely the dibenzylammonium ion and BMP25C8. This comparison is made possible by determining an average association constant (K-AVE) for the binding of each recognition site on the cluster with the corresponding monovalent ligand. We have found that the clustering of recognition sites together in one molecule is detrimental to their individual abilities to bind monovalent ligands. In the case of the polyvalent interaction between the hexakisBMP25C8 cluster and divalent dialkylammonium ions, an association constant, K-POLY, was calculated from the value of K-AVE determined for the complexation of the individual component recognition sites. This polyvalent interaction is significantly stronger than that associated with the averaged monovalent interactions.

  DOI：

  10.1021/jo030283o
• 作为产物：
  描述：

  1,2-bis[4-(formyl)phenyl]disulfane 在 sodium tetrahydroborate 作用下， 以 四氢呋喃 、 甲醇 、 甲苯 为溶剂， 生成 4-(benzylaminomethyl)thiophenol
  参考文献：
  名称：

  Polyvalent Interactions in Unnatural Recognition Processes

  摘要：

  The synthesis of two cluster compounds, one containing six secondary dialkylammonium ion centers and the other possessing six benzo-m-phenylene[25]crown-8 (BMP25C8) macrocycles, both appended to hexakis(thiophenyl)benzene cores, is described. The binding of these clusters with complementary mono- and divalent ligands is investigated with NMR spectroscopy to probe polyvalency in these unnatural recognition systems. The ability of the two different families of clusters to bind complementary monovalent ligands is compared with that of the monovalent receptor pair, namely the dibenzylammonium ion and BMP25C8. This comparison is made possible by determining an average association constant (K-AVE) for the binding of each recognition site on the cluster with the corresponding monovalent ligand. We have found that the clustering of recognition sites together in one molecule is detrimental to their individual abilities to bind monovalent ligands. In the case of the polyvalent interaction between the hexakisBMP25C8 cluster and divalent dialkylammonium ions, an association constant, K-POLY, was calculated from the value of K-AVE determined for the complexation of the individual component recognition sites. This polyvalent interaction is significantly stronger than that associated with the averaged monovalent interactions.

  DOI：

  10.1021/jo030283o

文献信息

• Polyvalent Interactions in Unnatural Recognition Processes
  作者：James N. Lowe、David A. Fulton、Sheng-Hsien Chiu、Arkadij M. Elizarov、Stuart J. Cantrill、Stuart J. Rowan、J. Fraser Stoddart

  DOI：10.1021/jo030283o

  日期：2004.6.1

  The synthesis of two cluster compounds, one containing six secondary dialkylammonium ion centers and the other possessing six benzo-m-phenylene[25]crown-8 (BMP25C8) macrocycles, both appended to hexakis(thiophenyl)benzene cores, is described. The binding of these clusters with complementary mono- and divalent ligands is investigated with NMR spectroscopy to probe polyvalency in these unnatural recognition systems. The ability of the two different families of clusters to bind complementary monovalent ligands is compared with that of the monovalent receptor pair, namely the dibenzylammonium ion and BMP25C8. This comparison is made possible by determining an average association constant (K-AVE) for the binding of each recognition site on the cluster with the corresponding monovalent ligand. We have found that the clustering of recognition sites together in one molecule is detrimental to their individual abilities to bind monovalent ligands. In the case of the polyvalent interaction between the hexakisBMP25C8 cluster and divalent dialkylammonium ions, an association constant, K-POLY, was calculated from the value of K-AVE determined for the complexation of the individual component recognition sites. This polyvalent interaction is significantly stronger than that associated with the averaged monovalent interactions.