1-(tert-butyl)-5-(2-nitrophenyl)-1H-pyrazole | 1335517-34-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 1-(tert-butyl)-5-(2-nitrophenyl)-1H-pyrazole
• CAS: 1335517-34-4
• 化学式: C₁₃H₁₅N₃O₂
• 分子量: 245.281
• InChiKey: VXGYESFFRPBUCA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.21
• 重原子数：
  18.0
• 可旋转键数：
  2.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  60.96
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  1-(tert-butyl)-5-(2-nitrophenyl)-1H-pyrazole 在 palladium 10% on activated carbon 、 氢气 作用下， 以 乙醇 为溶剂， 20.0 ℃ 、300.01 kPa 条件下， 反应 3.0h， 以92%的产率得到5-(2-aminophenyl)-1-(tert-butyl)-1H-pyrazole
  参考文献：
  名称：

  A Simple Synthesis of 5-(2-Aminophenyl)-1H-pyrazoles

  摘要：

  AbstractA four‐step synthesis of 1‐substituted 5‐(2‐aminophenyl)‐1H‐pyrazoles 5 as a novel type of histamine analogs and versatile building blocks for further transformations was developed. The synthesis starts from commercially available 2‐nitroacetophenone (12), which is converted into the enamino ketone 13 as the key intermediate. Cyclization of the key intermediate 13 with monosubstituted hydrazines 14a–14l afforded the 5‐(2‐nitrophenyl)‐1H‐pyrazoles 17a–17l. Finally, catalytic hydrogenation of the nitro compounds 17a, 17c–17e, and 17g–17j furnished the title compounds 5a, 5c–5e, and 5g–5j, respectively, in good yields. As demonstrated by some further transformations, additional functionalization of compounds 17 and 5 is feasible, either by electrophilic substitution at C(4) of the pyrazole ring, or at the NH2 group.

  DOI：

  10.1002/hlca.201100055
• 作为产物：
  描述：

  邻硝基苯乙酮 以 丙醇 、 甲苯 为溶剂， 反应 8.5h， 生成 1-(tert-butyl)-5-(2-nitrophenyl)-1H-pyrazole
  参考文献：
  名称：

  A Simple Synthesis of 5-(2-Aminophenyl)-1H-pyrazoles

  摘要：

  AbstractA four‐step synthesis of 1‐substituted 5‐(2‐aminophenyl)‐1H‐pyrazoles 5 as a novel type of histamine analogs and versatile building blocks for further transformations was developed. The synthesis starts from commercially available 2‐nitroacetophenone (12), which is converted into the enamino ketone 13 as the key intermediate. Cyclization of the key intermediate 13 with monosubstituted hydrazines 14a–14l afforded the 5‐(2‐nitrophenyl)‐1H‐pyrazoles 17a–17l. Finally, catalytic hydrogenation of the nitro compounds 17a, 17c–17e, and 17g–17j furnished the title compounds 5a, 5c–5e, and 5g–5j, respectively, in good yields. As demonstrated by some further transformations, additional functionalization of compounds 17 and 5 is feasible, either by electrophilic substitution at C(4) of the pyrazole ring, or at the NH2 group.

  DOI：

  10.1002/hlca.201100055