ethyl 3-(1,3-dioxo-1,3-dihydro-isoindol-2-yl-methyl)-1H-pyrazole-5-carboxylate | 1257225-38-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异吲哚及其衍生物
• 英文名称: ethyl 3-(1,3-dioxo-1,3-dihydro-isoindol-2-yl-methyl)-1H-pyrazole-5-carboxylate
• 英文别名: ethyl 5-[(1,3-dioxoisoindol-2-yl)methyl]-1H-pyrazole-3-carboxylate
• CAS: 1257225-38-9
• 化学式: C₁₅H₁₃N₃O₄
• 分子量: 299.286
• InChiKey: ZLJTTYDEWMFOLB-UHFFFAOYSA-N

物化性质

• 熔点：
  164-165.5 °C
• 沸点：
  538.3±45.0 °C(Predicted)
• 密度：
  1.446±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  92.4
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  重氮乙酸乙酯 、 N-丙炔基邻苯二甲酸胺 以 甲苯 为溶剂， 反应 16.0h， 以60%的产率得到ethyl 3-(1,3-dioxo-1,3-dihydro-isoindol-2-yl-methyl)-1H-pyrazole-5-carboxylate
  参考文献：
  名称：

  A facile synthesis of pyrazoles with multi-point structural diversity by 1,3-dipolar cycloaddition

  摘要：

  We describe the synthesis of diverse pyrazoles by 1,3-dipolar cycloaddition of ethyl diazoacetate with various acetylenes in refluxing toluene. The product pyrazoles are useful starting points for preparing a diverse collection of trisubstituted pyrazole carboxamides. For aryl and heteroaryl alkynes a single product is obtained while alkyl alkynes afford a ca. 6:1 mixture of regioisomers. The observed regioselectivity for the cycloaddition step and the ease of reaction are consistent with predictions derived from computing the HOMO-LUMO energies of the reactants. (C) 2010 Published by Elsevier Ltd.

  DOI：

  10.1016/j.tetlet.2010.09.012

文献信息

• A facile synthesis of pyrazoles with multi-point structural diversity by 1,3-dipolar cycloaddition
  作者：Kwai Ming J. Cheung、Jóhannes Reynisson、Edward McDonald

  DOI：10.1016/j.tetlet.2010.09.012

  日期：2010.11

  We describe the synthesis of diverse pyrazoles by 1,3-dipolar cycloaddition of ethyl diazoacetate with various acetylenes in refluxing toluene. The product pyrazoles are useful starting points for preparing a diverse collection of trisubstituted pyrazole carboxamides. For aryl and heteroaryl alkynes a single product is obtained while alkyl alkynes afford a ca. 6:1 mixture of regioisomers. The observed regioselectivity for the cycloaddition step and the ease of reaction are consistent with predictions derived from computing the HOMO-LUMO energies of the reactants. (C) 2010 Published by Elsevier Ltd.