3-(2-cyanophenyl)-2-(4-methoxybenzyl)-5-(4-methylphenyl)pyrazole-1-oxide

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 3-(2-cyanophenyl)-2-(4-methoxybenzyl)-5-(4-methylphenyl)pyrazole-1-oxide
• 英文别名: 2-[2-[(4-Methoxyphenyl)methyl]-5-(4-methylphenyl)-1-oxidopyrazol-1-ium-3-yl]benzonitrile
• 化学式: C₂₅H₂₁N₃O₂
• 分子量: 395.461
• InChiKey: FANZRUZLPKVGJY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  30
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  63.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  3-bromo-2-(4-methoxybenzyl)pyrazole 1-oxide 在 异丙基氯化镁 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 为溶剂， 反应 11.0h， 生成 3-(2-cyanophenyl)-2-(4-methoxybenzyl)-5-(4-methylphenyl)pyrazole-1-oxide
  参考文献：
  名称：

  Sequential Functionalization of Pyrazole 1-Oxides via Regioselective Metalation:  Synthesis of 3,4,5-Trisubstituted 1-Hydroxypyrazoles

  摘要：

  A range of 3,5-diarylated and 3,4,5-triarylated 2-(4-methoxybenzyl)pyrazole I-oxides have been prepared by regioselective deprotonation at C-5 or bromine-magnesium exchange at C-3 or C-4 followed by transmetalation with ZnCl2 and palladium(0)-catalyzed cross-coupling. Furthermore, the metalated pyrazole 1-oxides could be trapped with electrophiles. The sequential metalation/functionalization of the pyrazole I-oxides may follow the order C-5, C-3, C-4, or alternatively the order C-3, C-5, C-4. The 4-methoxybenzyl group of the functionalized 2-(4-methoxybenzyl)pyrazole 1-oxides could be removed by treatment with TFA and i-Pr3SiH in CH2Cl2, providing the corresponding functionalized 1-hydroxypyrazoles.

  DOI：

  10.1021/jo015997i

文献信息

• Sequential Functionalization of Pyrazole 1-Oxides via Regioselective Metalation:  Synthesis of 3,4,5-Trisubstituted 1-Hydroxypyrazoles
  作者：Anna Sif Paulson、Jørgen Eskildsen、Per Vedsø、Mikael Begtrup

  DOI：10.1021/jo015997i

  日期：2002.5.1

  A range of 3,5-diarylated and 3,4,5-triarylated 2-(4-methoxybenzyl)pyrazole I-oxides have been prepared by regioselective deprotonation at C-5 or bromine-magnesium exchange at C-3 or C-4 followed by transmetalation with ZnCl2 and palladium(0)-catalyzed cross-coupling. Furthermore, the metalated pyrazole 1-oxides could be trapped with electrophiles. The sequential metalation/functionalization of the pyrazole I-oxides may follow the order C-5, C-3, C-4, or alternatively the order C-3, C-5, C-4. The 4-methoxybenzyl group of the functionalized 2-(4-methoxybenzyl)pyrazole 1-oxides could be removed by treatment with TFA and i-Pr3SiH in CH2Cl2, providing the corresponding functionalized 1-hydroxypyrazoles.