1-(methoxymethyl)-5-methyl-1H-pyrazole-3,4-dicarboxylic acid dimethyl ester | 125541-65-3

• 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-(methoxymethyl)-5-methyl-1H-pyrazole-3,4-dicarboxylic acid dimethyl ester
• 英文别名: dimethyl 1-(methoxymethyl)-5-methylpyrazole-3,4-dicarboxylate
• CAS: 125541-65-3
• 化学式: C₁₀H₁₄N₂O₅
• 分子量: 242.232
• InChiKey: WIPFMOANTTXBSM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.37
• 重原子数：
  17.0
• 可旋转键数：
  4.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  79.65
• 氢给体数：
  0.0
• 氢受体数：
  7.0

反应信息

• 作为产物：
  描述：

  dimethyl 5-(methoxymethyl)-5-methylpyrazole-3,4-dicarboxylate 生成 1-(methoxymethyl)-5-methyl-1H-pyrazole-3,4-dicarboxylic acid dimethyl ester
  参考文献：
  名称：

  MAJCHRZAK, MICHAEL W.;JEFFERSON, ELIZABETH;WARKENTIN, JOHN, J. AMER. CHEM. SOC., 112,(1990) N, C. 2449-2451

  摘要：

  DOI：

文献信息

• Studies of formal [1,5]-sigmatropic thermal rearrangements of dimethyl 3-alkyl-3-methyl-3H-pyrazole-4,5-dicarboxylates and dimethyl 4-alkyl-5-methyl-4H-pyrazole-3,4-dicarboxylates
  作者：Elizabeth A. Jefferson、John Warkentin

  DOI：10.1021/ja00042a007

  日期：1992.7

  Studies of the thermal rearrangements of 3H-pyrazoles, 10a-e, in benzene/toluene, chloroform, and methanol solvents are described. The mechanism for rearrangement appears to be two-step, involving discrete ion-pair intermediates. Large rate enhancements for these rearrangements in methanol and cation trapping by methanol are consistent with the proposed mechanism. Observed rate constants for the rearrangements of 3H-pyrazoles 10c, 10d, and 10e in benzene-d6 were determined. Insight into the sense of rearrangement by an ion-pair mechanism is also provided by analysis of the H-1 NMR spectra of the product mixtures. 3H-Pyrazoles 10b and 10e rearrange to afford 4H-pyrazoles 13b and 13e, respectively, and the thermal rearrangements of these pyrazoles in benzene-d6 and methanol are described. Rate constants for the rearrangements of these more stable pyrazole isomers in benzene-d6 were also determined. Cation-trapping experiments with methanol suggest that the 4H-pyrazoles also rearrange by a two-step mechanism, involving discrete ion-pair intermediates. Furthermore, it appears that different ion-pair intermediates are formed from the 3H-pyrazoles 10b and 10e, compared to the 4H-pyrazoles 13b and 13e, on the basis of cation-trapping experiments.