1,3,5-tris((3,5-dihydroxybenzylthio)methyl)benzene | 943139-50-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 1,3,5-tris((3,5-dihydroxybenzylthio)methyl)benzene
• 英文别名: 5-[[3,5-Bis[(3,5-dihydroxyphenyl)methylsulfanylmethyl]phenyl]methylsulfanylmethyl]benzene-1,3-diol；5-[[3,5-bis[(3,5-dihydroxyphenyl)methylsulfanylmethyl]phenyl]methylsulfanylmethyl]benzene-1,3-diol
• CAS: 943139-50-2
• 化学式: C₃₀H₃₀O₆S₃
• 分子量: 582.763
• InChiKey: MMMHHXIIXGSHFF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  39
• 可旋转键数：
  12
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  197
• 氢给体数：
  6
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  1,3,5-tris((3,5-dihydroxybenzylthio)methyl)benzene 、 二溴甲烷 在 caesium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 8.0h， 以18%的产率得到4,6,12,14,33,35-Hexaoxa-21,29,39-trithiaheptacyclo[15.15.3.39,25.13,31.17,11.115,19.123,27]dotetraconta-1(32),2,7(42),8,10,15(41),16,18,23(37),24,26,31(36)-dodecaene
  参考文献：
  名称：

  Macrotricycles Featuring a π-Basic Tetrahedral Cavity:  Preference for NH₄⁺ Detected by Electrospray Ionization Mass Spectrometry

  摘要：

  Cation-pi interactions play an important role in biology. The title compounds are C-3-symmetric macrotricycles built from resorcinol, a pi electron-rich arene. They were prepared in up to 18% yield by intramolecular cyclization of 1,3,5-trisubstituted benzene tripods bearing pendant resorcinol groups, with methylene acetal bridges. Positive ESI-MS showed that these receptors recognize NH4+ over K+, and poorly respond to the large t-BuNH3+ cation, suggesting that they bind NH4+ intramolecularly, presumably via cation-pi interactions.

  DOI：

  10.1021/ol070498a
• 作为产物：
  描述：

  1,3,5-三(溴甲基)苯 在 sodium hydride 、 对甲苯磺酸 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 反应 2.0h， 生成 1,3,5-tris((3,5-dihydroxybenzylthio)methyl)benzene
  参考文献：
  名称：

  Macrotricycles Featuring a π-Basic Tetrahedral Cavity:  Preference for NH₄⁺ Detected by Electrospray Ionization Mass Spectrometry

  摘要：

  Cation-pi interactions play an important role in biology. The title compounds are C-3-symmetric macrotricycles built from resorcinol, a pi electron-rich arene. They were prepared in up to 18% yield by intramolecular cyclization of 1,3,5-trisubstituted benzene tripods bearing pendant resorcinol groups, with methylene acetal bridges. Positive ESI-MS showed that these receptors recognize NH4+ over K+, and poorly respond to the large t-BuNH3+ cation, suggesting that they bind NH4+ intramolecularly, presumably via cation-pi interactions.

  DOI：

  10.1021/ol070498a

文献信息

• Macrotricycles Featuring a π-Basic Tetrahedral Cavity:  Preference for NH₄⁺ Detected by Electrospray Ionization Mass Spectrometry
  作者：Anne Lélias-Vanderperre、Jean-Claude Chambron、Enrique Espinosa、Peran Terrier、Emmanuelle Leize-Wagner

  DOI：10.1021/ol070498a

  日期：2007.8.1

  Cation-pi interactions play an important role in biology. The title compounds are C-3-symmetric macrotricycles built from resorcinol, a pi electron-rich arene. They were prepared in up to 18% yield by intramolecular cyclization of 1,3,5-trisubstituted benzene tripods bearing pendant resorcinol groups, with methylene acetal bridges. Positive ESI-MS showed that these receptors recognize NH4+ over K+, and poorly respond to the large t-BuNH3+ cation, suggesting that they bind NH4+ intramolecularly, presumably via cation-pi interactions.