4-nitrobenzaldehyde N-methyl-N-phenylhydrazone | 790-48-7

• 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: 4-nitrobenzaldehyde N-methyl-N-phenylhydrazone
• 英文别名: 4-nitro-benzaldehyde-(methyl-phenyl-hydrazone)；4-Nitro-benzaldehyd-(methyl-phenyl-hydrazon)；p-Nitro-benzaldehyd-(N-methyl-N-phenyl-hydrazon)；p-Nitrobenzaldehyd-(N-methyl-N-phenyl)-hydrazon；1-Methyl-2-p-nitrobenzyliden-1-phenylhydrazin；4-Nitrobenzaldehyd-N-methyl-N-phenylhydrazon；N-methyl-N-[(4-nitrophenyl)methylideneamino]aniline
• CAS: 790-48-7
• 化学式: C₁₄H₁₃N₃O₂
• 分子量: 255.276
• InChiKey: UYKWINPUYBGLDJ-UHFFFAOYSA-N

物化性质

• 熔点：
  130 °C
• 沸点：
  400.3±47.0 °C(Predicted)
• 密度：
  1.15±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  61.4
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  氟三溴甲烷 、 4-nitrobenzaldehyde N-methyl-N-phenylhydrazone 在 tris(triphenylphosphine)ruthenium(II) chloride 、 potassium carbonate 作用下， 以 二乙二醇二甲醚 为溶剂， 反应 15.0h， 以40%的产率得到4-fluoro-3-(4-nitrophenyl)-1H-1-phenylpyrazole
  参考文献：
  名称：

  Ruthenium-Catalyzed Tandem C–H Fluoromethylation/Cyclization of N-Alkylhydrazones with CBr₃F: Access to 4-Fluoropyrazoles

  摘要：

  4-Fluoropyrazoles are accessible in a single step from readily available aldehyde-derived N-alkylhydrazones through double C-H fluoroalkylation with tribromofluoromethane (CBr3F). RuCl2(PPh3)(3) has been proven to be the most efficient catalyst for this transformation when compared to a range of other Cu-, Pd-, or Fe-based catalyst systems.

  DOI：

  10.1021/acs.joc.7b00085
• 作为产物：
  描述：

  N-[叔丁基(二苯基)甲硅烷基]-1-苯基甲胺 在 次氯酸叔丁酯 、 间氯过氧苯甲酸 、 potassium hydroxide 作用下， 以 二氯甲烷 、 氯仿 、 乙腈 为溶剂， 反应 94.5h， 生成 4-nitrobenzaldehyde N-methyl-N-phenylhydrazone
  参考文献：
  名称：

  N-Silyloxaziridines: Synthesis and Use for Electrophilic Amination

  摘要：

  N-Silyloxaziridines were synthesized for the first time. Their tert-butyldiphenylsilyl (TBDPS) derivatives were stable reagents that were prepared on a multigram scale in three steps and in 44% overall yield from the corresponding benzylamines. They were mild electrophilic aminating reagents that reacted at room temperature with diversely substituted primary and secondary amines to produce N-monoalkyl or N,N-dialkyl benzaldehyde hydrazones in 44-87% yield.

  DOI：

  10.1021/jo302182t

文献信息

• Labhardt; v. Zembrzuski, Chemische Berichte, 1899, vol. 32, p. 3062
  作者：Labhardt、v. Zembrzuski

  DOI：——

  日期：——
• Ciusa; Padoa, Atti della Accademia Nazionale dei Lincei, Classe di Scienze Fisiche, Matematiche e Naturali, Rendiconti, 1909, vol. <5> 18 II, p. 622
  作者：Ciusa、Padoa

  DOI：——

  日期：——
• <i>N</i>-Silyloxaziridines: Synthesis and Use for Electrophilic Amination
  作者：Nicolas Richy、Mohammed Ghoraf、Joëlle Vidal

  DOI：10.1021/jo302182t

  日期：2012.12.7

  N-Silyloxaziridines were synthesized for the first time. Their tert-butyldiphenylsilyl (TBDPS) derivatives were stable reagents that were prepared on a multigram scale in three steps and in 44% overall yield from the corresponding benzylamines. They were mild electrophilic aminating reagents that reacted at room temperature with diversely substituted primary and secondary amines to produce N-monoalkyl or N,N-dialkyl benzaldehyde hydrazones in 44-87% yield.
• Ruthenium-Catalyzed Tandem C–H Fluoromethylation/Cyclization of <i>N</i>-Alkylhydrazones with CBr₃F: Access to 4-Fluoropyrazoles
  作者：Alexis Prieto、Didier Bouyssi、Nuno Monteiro

  DOI：10.1021/acs.joc.7b00085

  日期：2017.3.17

  4-Fluoropyrazoles are accessible in a single step from readily available aldehyde-derived N-alkylhydrazones through double C-H fluoroalkylation with tribromofluoromethane (CBr3F). RuCl2(PPh3)(3) has been proven to be the most efficient catalyst for this transformation when compared to a range of other Cu-, Pd-, or Fe-based catalyst systems.