1,4-bis((4-nitro-3,5-dimethyl-1H-pyrazol-1-yl)methyl)benzene | 1170237-93-0

• 分子结构分类: 有机化合物 - 有机1,3-偶极化合物 - 烯丙基型1,3-偶极有机化合物
• 英文名称: 1,4-bis((4-nitro-3,5-dimethyl-1H-pyrazol-1-yl)methyl)benzene
• 英文别名: 1-[[4-[(3,5-Dimethyl-4-nitropyrazol-1-yl)methyl]phenyl]methyl]-3,5-dimethyl-4-nitropyrazole
• CAS: 1170237-93-0
• 化学式: C₁₈H₂₀N₆O₄
• 分子量: 384.395
• InChiKey: UYJRTWGDPSYGTB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  28
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  127
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  对二甲苯 在 溴 、 potassium hydroxide 作用下， 以 二甲基亚砜 为溶剂， 反应 6.0h， 生成 1,4-bis((4-nitro-3,5-dimethyl-1H-pyrazol-1-yl)methyl)benzene
  参考文献：
  名称：

  Synthesis, structural, and biological evaluation of the arene-linked pyrazolyl methane ligands and their d9/d10 metal complexes

  摘要：

  A series of the p-bis[(1-pyrazolyl)methyl] benzene ligands (L-1-L-6) in the DMSO system were synthesized. In the mean time, by using the ligands as a linker, a new family of transition metal coordination polymers, namely, [Cu-2(L-1)(2)Cl-4] (1), [Cu-2(L-2)(2)Cl-4] (2), [Ag(L-2)(NO3)] (3). [Zn-2(L-2)(2)(SCN)(4)] (4) and [Cd-2(L-2)(SCN)(4)] (5) [L-1 = 1,4-bis((1H-pyrazol-1-yl)methyl)benzene; L-2 = 1,4-bis(3,5-dimethyl-1H-pyrazol-1-yl)methyl)benzene] have been constructed by the reaction of the p-bis[(1-pyrazolyl)methyl]benzene and corresponding to the transition metal compounds in a mixed solution of CH3OH/C2H5OH at mild temperature condition. All the coordination polymers and p-bis[(1-pyrazolyl)methyl]benzene ligands were characterized by elemental analysis, IR spectroscopy, H-1 NMR and C-13 NMR, and some of them were characterized by UV spectroscopy, thermogravimetric analysis, X-ray powder and X-ray single-crystal diffraction. Structural analyses reveal that the ligands L-3-L-5 (L-3 = 1,4-bis((4-iodo-1H-pyrazol-1-yl)methyl)benzene, L-4 = 1,4-bis((4-iodo-3,5-dimethyl-1H-pyrazol-1-yl)methyl)benzene, L-5 = 1,4-bis((4-nitro-1H-pyrazol-1-yl)methyl) benzene,L-6 = 1,4-bis((4-nitro-3,5-dimethyl-1H-pyrazol-1-yl) methyl) benzene) are discrete organic compound molecules and the complexes 1-5 are 1D M-L-M coordination polymers, which are further interlinked via hydrogen bonds resulting in 2D or even 3D supermolecular networks. The luminescent properties of the coordination polymers 3,4 and 5 were examined by luminescence spectra. The analytic results indicate that different metal complexes with the same ligand have different influence on the characteristic photoluminescence. Furthermore, the cytotoxicity of the ligands L-1-L-6 and complexes 1-5 were evaluated against hepG2 cells. For the ligands of L-1-L-6, the different substituents of the pyrazole ring slightly influenced the cytotoxicity of the cell. It is found that nitro-compounds have shown the highest cytotoxicity under the same concentration condition. The cytotoxic activity of the complexes 1-5 are strongly increased by the introduction of the transition metals. (c) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.poly.2012.08.016

文献信息

• Molecular design and the optimum synthetic route of the compounds with multi-pyrazole and its derivatives and the potential application in antibacterial agents
  作者：Ji-Xiao Wang、Zi-Ran Zhu、Feng-Ying Bai、Xin-Yu Wang、Xiao-Xi Zhang、Yong-Heng Xing

  DOI：10.1016/j.poly.2015.06.020

  日期：2015.10

  Molecular design and efficient synthetic procedures have been developed for pyrazole and its derivatives with different linkers. In particular, twelve compounds with -I or -NO2 substituted groups on the pyrazole ring were synthesized for the first time. These compounds are characterized by element analysis, IR, HNMR, M.P. and X-ray diffraction. In addition, some compounds and corresponding complexes were also assayed in vitro for their ability to inhibit the growth of representative Gram-positive bacteria, Gram-negative bacteria and the fungus. It was worthwhile to note that some compounds could be used as potential antibacterial agents. (C) 2015 Elsevier Ltd. All rights reserved.
• Synthesis, structural, and biological evaluation of the arene-linked pyrazolyl methane ligands and their d9/d10 metal complexes
  作者：Xin-Yu Wang、Shu-Qing Liu、Chun-Yan Zhang、Ge Song、Feng-Ying Bai、Yong-Heng Xing、Zhan Shi

  DOI：10.1016/j.poly.2012.08.016

  日期：2012.10

  A series of the p-bis[(1-pyrazolyl)methyl] benzene ligands (L-1-L-6) in the DMSO system were synthesized. In the mean time, by using the ligands as a linker, a new family of transition metal coordination polymers, namely, [Cu-2(L-1)(2)Cl-4] (1), [Cu-2(L-2)(2)Cl-4] (2), [Ag(L-2)(NO3)] (3). [Zn-2(L-2)(2)(SCN)(4)] (4) and [Cd-2(L-2)(SCN)(4)] (5) [L-1 = 1,4-bis((1H-pyrazol-1-yl)methyl)benzene; L-2 = 1,4-bis(3,5-dimethyl-1H-pyrazol-1-yl)methyl)benzene] have been constructed by the reaction of the p-bis[(1-pyrazolyl)methyl]benzene and corresponding to the transition metal compounds in a mixed solution of CH3OH/C2H5OH at mild temperature condition. All the coordination polymers and p-bis[(1-pyrazolyl)methyl]benzene ligands were characterized by elemental analysis, IR spectroscopy, H-1 NMR and C-13 NMR, and some of them were characterized by UV spectroscopy, thermogravimetric analysis, X-ray powder and X-ray single-crystal diffraction. Structural analyses reveal that the ligands L-3-L-5 (L-3 = 1,4-bis((4-iodo-1H-pyrazol-1-yl)methyl)benzene, L-4 = 1,4-bis((4-iodo-3,5-dimethyl-1H-pyrazol-1-yl)methyl)benzene, L-5 = 1,4-bis((4-nitro-1H-pyrazol-1-yl)methyl) benzene,L-6 = 1,4-bis((4-nitro-3,5-dimethyl-1H-pyrazol-1-yl) methyl) benzene) are discrete organic compound molecules and the complexes 1-5 are 1D M-L-M coordination polymers, which are further interlinked via hydrogen bonds resulting in 2D or even 3D supermolecular networks. The luminescent properties of the coordination polymers 3,4 and 5 were examined by luminescence spectra. The analytic results indicate that different metal complexes with the same ligand have different influence on the characteristic photoluminescence. Furthermore, the cytotoxicity of the ligands L-1-L-6 and complexes 1-5 were evaluated against hepG2 cells. For the ligands of L-1-L-6, the different substituents of the pyrazole ring slightly influenced the cytotoxicity of the cell. It is found that nitro-compounds have shown the highest cytotoxicity under the same concentration condition. The cytotoxic activity of the complexes 1-5 are strongly increased by the introduction of the transition metals. (c) 2012 Elsevier Ltd. All rights reserved.