(4E,5Z)-5-[bis(trimethylsilyl)hydrazin-1-ylidene]-1,3-(bis(trimethylsilyl)-4-(2-trimethylsilyl)hydrazin-1-ylidene)pyrazole | 1402147-99-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 亚胺内酰胺
• 英文名称: (4E,5Z)-5-[bis(trimethylsilyl)hydrazin-1-ylidene]-1,3-(bis(trimethylsilyl)-4-(2-trimethylsilyl)hydrazin-1-ylidene)pyrazole
• 英文别名: (4E,5Z)-5-[bis(trimethylsilyl)hydrazinylidene]-1,3-bis(trimethylsilyl)-4-(trimethylsilylhydrazinylidene)pyrazole
• CAS: 1402147-99-2
• 化学式: C₁₈H₄₆N₆Si₅
• 分子量: 487.031
• InChiKey: PCAISLAFOWLTDX-YZXPOQMXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.44
• 重原子数：
  29.0
• 可旋转键数：
  7.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  55.59
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为产物：
  描述：

  Bis(trimethylsilyl)aminoisocyanid 在 三氟甲磺酸 、 三(五氟苯基)硼烷 作用下， 以 正己烷 、 氘代苯 为溶剂， 反应 242.0h， 生成 (4E,5Z)-5-[bis(trimethylsilyl)hydrazin-1-ylidene]-1,3-(bis(trimethylsilyl)-4-(2-trimethylsilyl)hydrazin-1-ylidene)pyrazole
  参考文献：
  名称：

  Catalytic Trimerization of Bis-silylated Diazomethane

  摘要：

  (Me3Si)(2)CNN isomerizes upon addition of traces of [Me3Si](+) ions to give (Me3Si)(2)NNC, which then undergoes an unusual trimerization reaction to give exclusively 4-diazenyl-3-hydrazinylpyrazole. As catalyst the isonitrilium ion, [(Me3Si)(2)NNC-(SiMe3)](+), was identified and fully characterized. Experiments and computations indicate a three-step reaction including isomerization of diazomethane, a C-C or N-C coupling, and a formal cycloaddition reaction. The kinetics and thermodynamics are discussed on the basis of DFT calculations.

  DOI：

  10.1021/ja308104k

文献信息

• Catalytic Trimerization of Bis-silylated Diazomethane
  作者：Muhammad Farooq Ibad、Peter Langer、Fabian Reiß、Axel Schulz、Alexander Villinger

  DOI：10.1021/ja308104k

  日期：2012.10.24

  (Me3Si)(2)CNN isomerizes upon addition of traces of [Me3Si](+) ions to give (Me3Si)(2)NNC, which then undergoes an unusual trimerization reaction to give exclusively 4-diazenyl-3-hydrazinylpyrazole. As catalyst the isonitrilium ion, [(Me3Si)(2)NNC-(SiMe3)](+), was identified and fully characterized. Experiments and computations indicate a three-step reaction including isomerization of diazomethane, a C-C or N-C coupling, and a formal cycloaddition reaction. The kinetics and thermodynamics are discussed on the basis of DFT calculations.