tetrakis(3,5-dimethyl-1H-pyrazol-1-yl)methane | 1198745-65-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: tetrakis(3,5-dimethyl-1H-pyrazol-1-yl)methane
• 英文别名: tetrakis(3,5-dimethylpyrazol-1-yl)methane；C(pzMe2)4；3,5-Dimethyl-1-[tris(3,5-dimethylpyrazol-1-yl)methyl]pyrazole；3,5-dimethyl-1-[tris(3,5-dimethylpyrazol-1-yl)methyl]pyrazole
• CAS: 1198745-65-1
• 化学式: C₂₁H₂₈N₈
• 分子量: 392.507
• InChiKey: SMBRYFHWUGGOMV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  29
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  71.3
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  三(3,5-二甲基-1-吡唑基)甲烷 在 正丁基锂 、 碘 作用下， 以 四氢呋喃 、 环己烷 为溶剂， 反应 3.5h， 以27%的产率得到tetrakis(3,5-dimethyl-1H-pyrazol-1-yl)methane
  参考文献：
  名称：

  Towards the functionalization of the methine carbon of a sterically hindered tris(pyrazolyl)methane: is a radical pathway envisageable? Synthesis and structure of tetrakis(3,5-dimethylpyrazolyl)methane

  摘要：

  Iodine oxidation, at -80 degrees C, of the carbanion in [{C-(pz(Me2))(3)}Li+(THF)] (1) (with pZ(Me2)=3,5-dimethylpyrazolyl) yields the C-centred radical in [{C-center dot(pz(Me2))(3)}Li(THF)](+) (1(+)), which, upon warming to room temperature, produces the unprecedented tetrakis(3,5-dimethylpyrazolyl)methane C(pz(Me2)), (3), the X-ray structure of which revealing intramolecular C-H center dot center dot center dot pi interactions between each 5-Me group and an adjacent pyrazolyl ring. Oxidation of the radical by O-2 appears to lead to the novel ether (pz(Me2))(3)C-O-C(pz(Me2))(3) (2). (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2009.09.006

文献信息

• A structural study of new tetrakis(1H-pyrazol-1-yl)methanes
  作者：Vera L.M. Silva、Artur M.S. Silva、Rosa M. Claramunt、Concepción López、Dionisia Sanz、Lourdes Infantes、Ángela Martínez López、Felipe Reviriego、Ibon Alkorta、José Elguero

  DOI：10.1016/j.tet.2019.130690

  日期：2019.11

  Hückel in 1937 from carbon tetrachloride and prepared again several times and the 3,5-dimethyl substituted 2 obtained serendipitously by Pombeiro in 2009. We have now extended this group to include four new derivatives 8, 9, 11 and 12 bearing methyl groups. The X-ray crystal structure of the four compounds has been determined. They have been studied by NMR both in solution (1H, 13C, 15N) and in the solid

  四（1- ħ -吡唑-1-基）甲烷是其中只有两个是已知的非常罕见的化合物：未取代的1经典由休克尔在1937年从四氯化碳获得并再次制备几次和3,5-二甲基取代的2获得偶然通过Pombeiro在2009年我们现在已经扩展这个组包括四个新的衍生物8，9，11和12个的轴承甲基。已经确定了四种化合物的X射线晶体结构。已通过NMR在溶液（1 H，13 C，15 N）和固态（13 C和13 H ）中对它们进行了研究。15 N）。六种化合物（几何形状，能量和绝对屏蔽）的DFT计算已用于讨论实验观察结果。
• Towards the functionalization of the methine carbon of a sterically hindered tris(pyrazolyl)methane: is a radical pathway envisageable? Synthesis and structure of tetrakis(3,5-dimethylpyrazolyl)methane
  作者：Laurent Benisvy、Riccardo Wanke、Maxim L. Kuznetsov、M. Fátima C. Guedes da Silva、Armando J.L. Pombeiro

  DOI：10.1016/j.tet.2009.09.006

  日期：2009.11

  Iodine oxidation, at -80 degrees C, of the carbanion in [C-(pz(Me2))(3)}Li+(THF)] (1) (with pZ(Me2)=3,5-dimethylpyrazolyl) yields the C-centred radical in [C-center dot(pz(Me2))(3)}Li(THF)](+) (1(+)), which, upon warming to room temperature, produces the unprecedented tetrakis(3,5-dimethylpyrazolyl)methane C(pz(Me2)), (3), the X-ray structure of which revealing intramolecular C-H center dot center dot center dot pi interactions between each 5-Me group and an adjacent pyrazolyl ring. Oxidation of the radical by O-2 appears to lead to the novel ether (pz(Me2))(3)C-O-C(pz(Me2))(3) (2). (C) 2009 Elsevier Ltd. All rights reserved.