dimethyl 5-methyl-1-phenyl-1H-pyrazole-3,4-dicarboxylate | 7189-00-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: dimethyl 5-methyl-1-phenyl-1H-pyrazole-3,4-dicarboxylate
• 英文别名: dimethyl 5-methyl-1-phenylpyrazole-3,4-dicarboxylate；5-methyl-1-phenyl-1H-pyrazole-3,4-dicarboxylic acid dimethyl ester；1-Phenyl-5-methyl-pyrazol-3,4-dicarbonsaeure-dimethylester；5-Methyl-1-phenylpyrazoldicarbonsaeure-(3,4)-dimethylester
• CAS: 7189-00-6
• 化学式: C₁₄H₁₄N₂O₄
• 分子量: 274.276
• InChiKey: IJWFVQJOKIBLCU-UHFFFAOYSA-N

物化性质

• 熔点：
  57-59.4 °C
• 沸点：
  194 °C(Press: 0.8 Torr)
• 密度：
  1.23±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  70.4
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  dimethyl 5-methyl-1-phenyl-1H-pyrazole-3,4-dicarboxylate 、 氢化铝锂 以81%的产率得到
  参考文献：
  名称：

  ANDERSON, W. K.;JONES, A. N., J. MED. CHEM., 1984, 27, N 12, 1559-1565

  摘要：

  DOI：
• 作为产物：
  描述：

  丁炔二酸二甲酯 、 5-methyl-1,4-diphenyl-1H-1,2,3-triazole 在 三氯化铝 、 silica gel 作用下， 反应 0.33h， 以57%的产率得到dimethyl 5-methyl-1-phenyl-1H-pyrazole-3,4-dicarboxylate
  参考文献：
  名称：

  Recyclable supported catalysts in microwave-assisted reactions: first Diels–Alder cycloaddition of a triazole ring

  摘要：

  We describe here the first example in which a 1,2,3-triazole ring acts as a diene towards DMAD in microwave-assisted solvent-free Diels-Alder cycloadditions. The extrusion of a molecule of a nitrile affords pyrazole derivatives as the products. The yields can be markedly increased by using a recyclable supported Lewis acid catalyst, which can be reused at least five times without a decrease in the yield. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2006.10.006

文献信息

• Rhodium-Catalyzed Addition–Cyclization of Hydrazines with Alkynes: Pyrazole Synthesis via Unexpected C–N Bond Cleavage
  作者：Deng Yuan Li、Xiao Feng Mao、Hao Jie Chen、Guo Rong Chen、Pei Nian Liu

  DOI：10.1021/ol501402p

  日期：2014.7.3

  Rhodium-catalyzed addition-cyclization of hydrazines with alkynes has been achieved to afford highly substituted pyrazoles under mild conditions. The cascade reaction involves two transformations: addition of the C-N bond of hydrazines to alkynes via unexpected C-N bond cleavage and intramolecular dehydration cyclization.
• GOTTHARDT H.; REITER F., CHEM. BER., 1979, 112, NO 4, 1206-1225
  作者：GOTTHARDT H.、 REITER F.

  DOI：——

  日期：——