diphenylbis(3,5-dimethylpyrazol-1-yl)methane | 153625-25-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: diphenylbis(3,5-dimethylpyrazol-1-yl)methane
• 英文别名: diphenylbis(3,5-dimethylpyrazolyl)methane；Pz''2C(C6H5)2；1H-Pyrazole, 1,1'-(diphenylmethylene)bis[3,5-dimethyl-；1-[(3,5-dimethylpyrazol-1-yl)-diphenylmethyl]-3,5-dimethylpyrazole
• CAS: 153625-25-3
• 化学式: C₂₃H₂₄N₄
• 分子量: 356.47
• InChiKey: VSEMISMYWHRJJB-UHFFFAOYSA-N

物化性质

• 沸点：
  539.3±50.0 °C(Predicted)
• 密度：
  1.10±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  27
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  35.6
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  diphenylbis(3,5-dimethylpyrazol-1-yl)methane 、 molybdenum hexacarbonyl 以 乙二醇二甲醚 为溶剂， 以74%的产率得到
  参考文献：
  名称：

  Synthesis and application of diphenylbis (3,5-dimethylpyrazol-1-yl)methane to form η2-arene complexes of molybdenum

  摘要：

  The neutral nitrogen-bidentate ligand, diphenylbis(3,5-dimethylpyrazol-1-yl)methane, Ph(2)CPz'(2), can readily be obtained by the reaction of Ph(2)CCl(2), with excess HPz' in a mixed-solvent system of toluene and triethylamine. It reacts with [Mo(CO)(6)] in 1,2-dimethoxyethane to give the eta(2)-arene complex, [Mo(Ph(2)CPz'(2))(CO)(3)] (1). This eta(2)-ligation appears to stabilize the coordination of Ph(2)CPz'(2) in forming [Mo(Ph(2)CPz'(2))(CO)(2)(N2C6H4NO2-p)][BPh(4)] (2) and [Mo(Ph(2)CPz'(2),)(CO)(2)(N(2)Ph)][BF4] (3) from the reaction of 1 with the appropriate diazonium salt but the stabilization seems not strong enough when [Mo{P(OMe)(3)}(3)(CO)(3)] is formed from the reaction of 1 with P(OMe)(3). The solid-state structures of 1 and 3 have been determined by X-ray crystallography: 1-CH2,Cl-2, monoclinic, P2(1)/n, a = 11.814(3), b = 11.7929(12), c = 19.460(6) Angstrom, beta = 95.605(24)degrees, V = 2698.2(11) Angstrom(3), Z = 4, D-calc = 1.530 g/cm(3), R = 0.044, R(w) = 0.036 based on 3218 reflections with I> 2 sigma(I); 2 (3)-1/2 hexane-1/2 CH3OH-1/2 H2O-1 CH2Cl2, monoclinic, C2/c, a = 41.766(10), b = 20.518(4), c = 16.784(3) Angstrom, beta = 101.871(18)degrees, V = 14076(5) Angstrom(3), Z = 8, D-calc = 1.457 g/cm(3), R = 0.064, R(w) = 0.059 based on 5865 reflections with I> 2 sigma(I). Two independent cations were found in the asymmetric unit of the crystals of 3. The average distance between the Mo and the two eta(2)-ligated carbon atoms is 2.574 Angstrom in 1 and 2.581 and 2.608 Angstrom in 3. The unfavourable disposition of the eta(2)-phenyl group with respect to the metal centre in 3 and the rigidity of the eta(2)-arene ligation excludes the possibility of any appreciable agostic C-H --> Mo interaction.

  DOI：

  10.1016/0022-328x(93)83147-n
• 作为产物：
  描述：

  3,5-二甲基吡唑 、 二氯二苯甲烷 在 三乙胺 作用下， 以 甲苯 为溶剂， 反应 72.0h， 以74%的产率得到diphenylbis(3,5-dimethylpyrazol-1-yl)methane
  参考文献：
  名称：

  Synthesis and application of diphenylbis (3,5-dimethylpyrazol-1-yl)methane to form η2-arene complexes of molybdenum

  摘要：

  The neutral nitrogen-bidentate ligand, diphenylbis(3,5-dimethylpyrazol-1-yl)methane, Ph(2)CPz'(2), can readily be obtained by the reaction of Ph(2)CCl(2), with excess HPz' in a mixed-solvent system of toluene and triethylamine. It reacts with [Mo(CO)(6)] in 1,2-dimethoxyethane to give the eta(2)-arene complex, [Mo(Ph(2)CPz'(2))(CO)(3)] (1). This eta(2)-ligation appears to stabilize the coordination of Ph(2)CPz'(2) in forming [Mo(Ph(2)CPz'(2))(CO)(2)(N2C6H4NO2-p)][BPh(4)] (2) and [Mo(Ph(2)CPz'(2),)(CO)(2)(N(2)Ph)][BF4] (3) from the reaction of 1 with the appropriate diazonium salt but the stabilization seems not strong enough when [Mo{P(OMe)(3)}(3)(CO)(3)] is formed from the reaction of 1 with P(OMe)(3). The solid-state structures of 1 and 3 have been determined by X-ray crystallography: 1-CH2,Cl-2, monoclinic, P2(1)/n, a = 11.814(3), b = 11.7929(12), c = 19.460(6) Angstrom, beta = 95.605(24)degrees, V = 2698.2(11) Angstrom(3), Z = 4, D-calc = 1.530 g/cm(3), R = 0.044, R(w) = 0.036 based on 3218 reflections with I> 2 sigma(I); 2 (3)-1/2 hexane-1/2 CH3OH-1/2 H2O-1 CH2Cl2, monoclinic, C2/c, a = 41.766(10), b = 20.518(4), c = 16.784(3) Angstrom, beta = 101.871(18)degrees, V = 14076(5) Angstrom(3), Z = 8, D-calc = 1.457 g/cm(3), R = 0.064, R(w) = 0.059 based on 5865 reflections with I> 2 sigma(I). Two independent cations were found in the asymmetric unit of the crystals of 3. The average distance between the Mo and the two eta(2)-ligated carbon atoms is 2.574 Angstrom in 1 and 2.581 and 2.608 Angstrom in 3. The unfavourable disposition of the eta(2)-phenyl group with respect to the metal centre in 3 and the rigidity of the eta(2)-arene ligation excludes the possibility of any appreciable agostic C-H --> Mo interaction.

  DOI：

  10.1016/0022-328x(93)83147-n

文献信息

• Synthesis and Characterization of a Series of (Diphenyldipyrazolylmethane)copper Complexes as Possible Precursors to Type I Blue Copper Protein Active Site Models
  作者：Janet L. Shaw、Thomas B. Cardon、Gary A. Lorigan、Christopher J. Ziegler

  DOI：10.1002/ejic.200300547

  日期：2004.3

  A series of copper complexes employing the neutral, bidentate, pyrazole-based ligand diphenyldipyrazolylmethane was synthesized and fully characterized by various techniques, including elemental analysis, EPR, and structure elucidation by single-crystal X-ray diffraction. The structures of compounds 3−8 reveal variable coordination environments at the copper center, ranging from square pyramidal to

  合成了一系列采用中性、双齿、吡唑基配体二苯基二吡唑基甲烷的铜配合物，并通过各种技术进行了充分表征，包括元素分析、EPR 和单晶 X 射线衍射结构解析。化合物 3-8 的结构揭示了铜中心的不同配位环境，范围从方形锥体到四面体，这取决于吡唑外围的空间体积和反离子的身份。与使用带负电荷的吡唑基硼酸盐或 β-二酮亚胺盐观察到的那些化合物相比，这些化合物的循环伏安法数据显示出正偏移的还原电位。这些结果表明，这些化合物可能会产生（硫醇）铜复合物，从而更准确地再现在蓝铜蛋白的电子转移过程中观察到的还原电位。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004)
• Synthesis and characterization of a series of diphenyldipyrazolylmethane complexes with zinc(II)
  作者：Janet L. Shaw、Kevin P. Gwaltney、Nikky Keer

  DOI：10.1016/j.ica.2008.10.024

  日期：2009.5

  The zinc(II) coordination chemistry of a series of diphenyldipyrazolylmethane ligands was explored using H-1 NMR and single crystal X-ray diffraction. Unsubstituted diphenyldipyrazolylmethane (dpdpm), diphenylbis(3-methylpyrazolyl) methane (dpdp'm), and diphenylbis(3,5-dimethylpyrazolyl) methane (dpdp '' m) were reacted with Zn(NO3)(2) to afford Zn(dpdpm)(NO3) 2, Zn(dpdp'm)(NO3)(2) and Zn(Pz '')(2)(NO3)(2) where Pz '' = 3,5-dimethylpyrazole, respectively. All attempts to isolate Zn(dpdp '' m)(NO3)(2) with the intact dpdp '' m ligand were unsuccessful due to decomposition of the ligand. These bidentate ligands support the formation of 1:1 ligand to metal complexes and structurally model the two histidine coordination mode common in zinc proteins. Published by Elsevier B. V.