1,3,5-tris[(4-bromo-3,5-dimethyl-1H-pyrazol-1-yl)methyl]-2,4,6-triethylbenzene | 436084-62-7

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 芳基卤化物
• 英文名称: 1,3,5-tris[(4-bromo-3,5-dimethyl-1H-pyrazol-1-yl)methyl]-2,4,6-triethylbenzene
• 英文别名: 1-[[3,5-Bis[(4-bromo-3,5-dimethylpyrazol-1-yl)methyl]-2,4,6-triethylphenyl]methyl]-4-bromo-3,5-dimethylpyrazole；1-[[3,5-bis[(4-bromo-3,5-dimethylpyrazol-1-yl)methyl]-2,4,6-triethylphenyl]methyl]-4-bromo-3,5-dimethylpyrazole
• CAS: 436084-62-7
• 化学式: C₃₀H₃₉Br₃N₆
• 分子量: 723.392
• InChiKey: RODAXTKBFSEZFY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.5
• 重原子数：
  39
• 可旋转键数：
  9
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  53.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  ammonium hexafluorophosphate 、 1,3,5-tris[(4-bromo-3,5-dimethyl-1H-pyrazol-1-yl)methyl]-2,4,6-triethylbenzene 以 氯仿 、 乙腈 为溶剂， 生成
  参考文献：
  名称：

  Tuning and Dissecting Electronic and Steric Effects in Ammonium Receptors:  Nonactin vs Artificial Receptors

  摘要：

  Ion selective electrodes (ISE) based on three different tripodal receptors (5, 6, and 7) have been investigated for sensing ammonium ion. Each receptor is based on three pyrazole groups that can accept three H-bonds from the bound ammonium ion. The receptor based on 4-bromo-3,5-dimethylpyrazole (6) is the most sensitive with a detection limit for ammonium ion of 2.5 x 10(-5) M at pH 8. The detection limits for the receptors based on 2,3-dimethylpyrazole (5) and unsubstitued pyrazole (7) are 1,0 x 10(-4) and 2.0 x 10(-4) M, respectively. The selectivities of the receptors 5, 6, and 7 for sensing ammonium ion over potassium ion (logK(NH4)(-)/(+)(K)) are -2.8, -2.3, and -1.7, respectively. In contrast, the detection limit and the selectivity of a nonactin-based ISE are 2.2 x 10(-5) M and -1.3, respectively. Crystallographic studies reveal that 6 accepts three H-bonds from the bound ammonium and singly protonated receptor 5 forms three H-bonds with the bound water molecule.

  DOI：

  10.1021/ja0174175
• 作为产物：
  描述：

  1,3,5-三(溴甲基)-2,4,6-三乙基苯 在 溴 、 sodium hydride 作用下， 以 四氢呋喃 、 氯仿 为溶剂， 反应 4.33h， 生成 1,3,5-tris[(4-bromo-3,5-dimethyl-1H-pyrazol-1-yl)methyl]-2,4,6-triethylbenzene
  参考文献：
  名称：

  Tuning and Dissecting Electronic and Steric Effects in Ammonium Receptors:  Nonactin vs Artificial Receptors

  摘要：

  Ion selective electrodes (ISE) based on three different tripodal receptors (5, 6, and 7) have been investigated for sensing ammonium ion. Each receptor is based on three pyrazole groups that can accept three H-bonds from the bound ammonium ion. The receptor based on 4-bromo-3,5-dimethylpyrazole (6) is the most sensitive with a detection limit for ammonium ion of 2.5 x 10(-5) M at pH 8. The detection limits for the receptors based on 2,3-dimethylpyrazole (5) and unsubstitued pyrazole (7) are 1,0 x 10(-4) and 2.0 x 10(-4) M, respectively. The selectivities of the receptors 5, 6, and 7 for sensing ammonium ion over potassium ion (logK(NH4)(-)/(+)(K)) are -2.8, -2.3, and -1.7, respectively. In contrast, the detection limit and the selectivity of a nonactin-based ISE are 2.2 x 10(-5) M and -1.3, respectively. Crystallographic studies reveal that 6 accepts three H-bonds from the bound ammonium and singly protonated receptor 5 forms three H-bonds with the bound water molecule.

  DOI：

  10.1021/ja0174175

文献信息

• Synthesis of Tripodal and Hexapodal Pyrazole- and Benzimidazole-Bearing Compounds
  作者：Monika Mazik、Niklas Koch

  DOI：10.1055/s-0033-1338518

  日期：——

  The syntheses of eight new tripodal and hexapodal benzimidazole- and pyrazole-bearing compounds, which are all potentially applicable for use as artificial receptors, are described. The prepared compounds contain either bromo-substituted heteroaromatic rings, able to participate in halogen-bonding interactions, or their analogues lacking the bromo substituents. Furthermore, the preparation of a new trisbenzimidazolium cage is included in this work. All used practical synthetic procedures are facilely accomplishable and provide the products in good to excellent yields. In addition, slightly modified, simplified synthetic procedures for five known tripodal compounds, which lead to better yields than those previously reported, are also detailed.
• Tuning and Dissecting Electronic and Steric Effects in Ammonium Receptors:  Nonactin vs Artificial Receptors
  作者：Jik Chin、Jinho Oh、Sang Yong Jon、Sang Hyun Park、Christian Walsdorff、Brent Stranix、Assaad Ghoussoub、Seok Jong Lee、Hyun Jei Chung、Su-Moon Park、Kimoon Kim

  DOI：10.1021/ja0174175

  日期：2002.5.1

  Ion selective electrodes (ISE) based on three different tripodal receptors (5, 6, and 7) have been investigated for sensing ammonium ion. Each receptor is based on three pyrazole groups that can accept three H-bonds from the bound ammonium ion. The receptor based on 4-bromo-3,5-dimethylpyrazole (6) is the most sensitive with a detection limit for ammonium ion of 2.5 x 10(-5) M at pH 8. The detection limits for the receptors based on 2,3-dimethylpyrazole (5) and unsubstitued pyrazole (7) are 1,0 x 10(-4) and 2.0 x 10(-4) M, respectively. The selectivities of the receptors 5, 6, and 7 for sensing ammonium ion over potassium ion (logK(NH4)(-)/(+)(K)) are -2.8, -2.3, and -1.7, respectively. In contrast, the detection limit and the selectivity of a nonactin-based ISE are 2.2 x 10(-5) M and -1.3, respectively. Crystallographic studies reveal that 6 accepts three H-bonds from the bound ammonium and singly protonated receptor 5 forms three H-bonds with the bound water molecule.