1,3,5-Tris(pyrazol-1-ylmethyl)benzene | 172606-25-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 1,3,5-Tris(pyrazol-1-ylmethyl)benzene
• 英文别名: 1,3,5-Tris((1H-pyrazol-1-yl)methyl)benzene；1-[[3,5-bis(pyrazol-1-ylmethyl)phenyl]methyl]pyrazole
• CAS: 172606-25-6
• 化学式: C₁₈H₁₈N₆
• 分子量: 318.381
• InChiKey: IRBWFDAPHKEMOR-UHFFFAOYSA-N

物化性质

• 沸点：
  571.1±50.0 °C(Predicted)
• 密度：
  1.24±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  24
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.17
• 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：

  copper(II) perchlorate hexahydrate 、 1,3,5-Tris(pyrazol-1-ylmethyl)benzene 以 甲醇 为溶剂， 生成
  参考文献：
  名称：

  Syntheses and molecular structures of copper(II) complexes with 1,3,5-tris(pyrazol-1-ylmethyl)benzene

  摘要：

  A new trifunctional ligand, 1,3,5-tris(pyrazol-1-ylmethyl)benzene (L), has been prepared. It reacts with 1 equivalent of copper(II) perchlorate to form the complex [CuL2(ClO4)2(H2O)2] 1 and with 1.5 equivalents of copper(II) chloride to form [{Cu3L2Cl6(H2O)2}n] 3. The macromolecular complex [{Cu2L2Cl2(ClO4)2(H2O)4}n] 2 was formed by the reaction of 1 with 1 equivalent of CuCl2. Complex 3 can also be prepared from 2 with 1 equivalent of CuCl2 or from 1 with 2 equivalents of CuCl2. The mixed-metal complex [{Cu2CoL2Cl6(H2O)3}n] 4 was prepared from 2 with cobalt(II) chloride. The molecular structures of complexes 1, 2 and 4 have been characterized by X-ray diffraction: 1, monoclinic, space group P2(1), a = 10.255(1), b = 20.218(3), c = 10.316(2) angstrom, beta = 106.21(1)-degrees, Z = 2; 2, monoclinic, space group P2(1)/c, a = 11.288(2), b = 13.633(3), c = 15.173(3) angstrom, beta = 104.635(15)-degrees, Z = 2; 4, monoclinic, space group C2/c, a = 7.473(3), b = 22.137(7), c = 28.155(10) angstrom, beta = 96.21(3)-degrees, Z = 4. The co-ordination sphere of copper(II) in 1 and 2 is distorted square pyramidal and 2-4 have polymeric structures.

  DOI：

  10.1039/dt9930000687
• 作为产物：
  描述：

  吡唑 、 1,3,5-三(溴甲基)苯 在 四丁基氢氧化铵 sodium hydroxide 作用下， 以 苯 为溶剂， 反应 24.0h， 以64%的产率得到1,3,5-Tris(pyrazol-1-ylmethyl)benzene
  参考文献：
  名称：

  Poly(pyrazol-1-ylmethyl)Benzenes: New Multidentate Ligands

  摘要：

  通过吡唑与聚(溴甲基)苯的相转移催化烷基化反应，合成了十二种新的多齿聚(吡唑-1-基甲基)苯配体(5)-(16)，并完全分配了它们的 1H 和 13C n.m.r. 光谱。对 1,4-双（3,5-二甲基吡唑-1-基甲基）-2,3,5,6-四甲基苯的二质子化形式的四氯钯盐和六(吡唑-1-基甲基)苯进行了 X 射线晶体结构测定。

  DOI：

  10.1071/ch9951587

文献信息

• Structural Examination of Halogen-Bonded Co-Crystals of Tritopic Acceptors
  作者：Stefan Andree、Abhijeet Sinha、Christer Aakeröy

  DOI：10.3390/molecules23010163

  日期：——

  A series of tritopic N-heterocyclic compounds containing electrostatically and geometrically equivalent binding sites were synthesized and subjected to systematic co-crystallizations with selected perfluoroiodoarenes in order to map out their structural landscapes. More than 70% of the attempted reactions produced a co-crystal as indicated by IR spectroscopy. Four new crystal structures are reported and in all of them, at least one potential binding site on the acceptor is left vacant. The absence of halogen bonds to all sites can be ascribed primarily due to deactivation of the σ-hole on the iodo-arene donors and partially due to steric hindrance. The tritopic acceptors containing 5,6-dimethylbenzimidazole derivatives yield discrete tetrameric aggregates in the solid state, whereas the pyrazole and imidazole analogues assemble into halogen-bonded 1-D chains.

  一系列含有静电和几何等效结合位点的三亚甲基N-杂环化合物被合成，并经过系统的与选择的全氟碘芳烃共结晶，以绘制它们的结构景观。超过70%的尝试反应通过红外光谱表明产生了共结晶体。报道了四个新的晶体结构，在所有这些结构中，受体上至少有一个潜在的结合位点是空缺的。所有位点缺乏卤键主要归因于碘芳烃供体上σ孔的失活，部分归因于立体位阻。含有5,6-二甲基苯并咪唑衍生物的三亚甲基受体在固态中形成离散的四聚体聚集体，而吡唑和咪唑类似物组装成卤键结合的一维链。
• Self-Assembly of Ball-Shaped Molecular Complexes in Water
  作者：Thomas Grawe、Thomas Schrader、Reza Zadmard、Arno Kraft

  DOI：10.1021/jo025513y

  日期：2002.5.1

  We present a simple and versatile access to spheroidal molecular assemblies with pronounced stability in highly polar solvents. These complexes are composed of doubly and triply charged complementary building blocks based on ammonium or amidinium cations and phosphonate anions. Their high thermodynamic stability is best explained by the formation of a cyclic array of alternating positive and negative charges interconnected by a regular network of hydrogen bonds. Association constants reach 10(6) M-1 in methanol and often surpass 10(3) M-1 in water. The broad range of binding energies correlates well with the varying degree of preorganization of both complex partners. As a byproduct of these investigations, new recognition motifs for histidine and arginine esters and the unsubstituted guanidinium ion are proposed. The additional introduction of methyl groups in the 2-, 4-, and 6-positions of the central benzene ring in either cations or anions causes a marked drop in the corresponding K-a values of 1 order of magnitude; the related rotational barriers were estimated at 0.3-2.1 kcal/mol. Spontaneous formation of defined 2:1 complexes from three components has also been observed.