(E)-ethyl 7-(2-dimethylaminovinyl)pyrazolo<1,5-a>pyrimidin-6-carboxylate | 148191-33-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡唑并嘧啶类
• 英文名称: (E)-ethyl 7-(2-dimethylaminovinyl)pyrazolo<1,5-a>pyrimidin-6-carboxylate
• 英文别名: 6-ethoxycarbonyl-7-(2-dimethylaminovinyl)pyrazolo<1,5-a>pyrimidine；(E)-ethyl 7-(2-dimethylaminovinyl)pyrazolo[1,5-a]pyrimidin-6-carboxylate；ethyl 7-[(E)-2-(dimethylamino)vinyl]pyrazolo[1,5-a]pyrimidine-6-carboxylate；ethyl 7-[(E)-2-(dimethylamino)ethenyl]pyrazolo[1,5-a]pyrimidine-6-carboxylate
• CAS: 148191-33-7
• 化学式: C₁₃H₁₆N₄O₂
• 分子量: 260.296
• InChiKey: YNSCSRJISOVTFF-SOFGYWHQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  59.7
• 氢给体数：
  0
• 氢受体数：
  5

安全信息

• 危险等级：
  IRRITANT

反应信息

• 作为反应物：
  描述：

  (E)-ethyl 7-(2-dimethylaminovinyl)pyrazolo<1,5-a>pyrimidin-6-carboxylate 在 ammonium acetate 作用下， 以 溶剂黄146 为溶剂， 反应 1.0h， 以78%的产率得到吡唑并[1,5-A]吡啶并[3,4-E]嘧啶-6(7H)-酮
  参考文献：
  名称：

  Synthesis and preliminary evaluation of pyrazolo[1,5-a]pyrido[3,4-e]pyrimidin-6(7H)-ones and related compounds, as benzodiazepine receptor ligands and anticonvulsant agents

  摘要：

  DOI：

  10.1016/0223-5234(92)90033-w
• 作为产物：
  描述：

  N,N-二甲基甲酰胺 、 乙基7-甲基吡唑并[1,5-a]嘧啶-6-羧酸酯 在 哌啶 作用下， 以 N,N-二甲基乙酰胺 为溶剂， 以78%的产率得到(E)-ethyl 7-(2-dimethylaminovinyl)pyrazolo<1,5-a>pyrimidin-6-carboxylate
  参考文献：
  名称：

  Synthesis and preliminary evaluation of pyrazolo[1,5-a]pyrido[3,4-e]pyrimidin-6(7H)-ones and related compounds, as benzodiazepine receptor ligands and anticonvulsant agents

  摘要：

  DOI：

  10.1016/0223-5234(92)90033-w

文献信息

• Chemistry of substituted pyrazolo[1,5-a]pyrimidines. Part 5. 7-Oxo-6-[pyrazol-3′(5′)-yl]-4,7-dihydropyrazolo[1,5-a]pyrimidines from 6-ethoxycarbonyl-7-(2-dimethylaminovinyl)pyrazolo[1,5-a]-pyrimidines: elucidation of the reaction mechanism through NMR spectroscopy and X-ray diffraction analysis
  作者：Stefano Chimichi、Fabrizio Bruni、Barbara Cosimelli、Silvia Selleri、Giovanni Valle

  DOI：10.1039/p29960001147

  日期：——

  The reaction of 6-ethoxycarbonyl-7-(2-dimethylaminovinyl)pyrazolo[1,5-alpha]pyrimidines 1a,b with hydrazine hydrate in acetic acid solution gave rise to 7-oxo-6-[pyrazol-3'(5')-yl]-4,7-dihydropyrazolo[1,5-alpha]pyrimidines 3a,b, a result very similar to the intramolecular cyclization previously reported for the corresponding 6-acetyl derivatives 1c,d. Treatment of compounds 3a,b with dimethyl sulfate gave rise to a mixture of the N-methyl derivatives 4a,b and 5a,b whose structures have; been unambiguously established on the basis of NMR spectroscopy and confirmed by the X-ray structure of compound 4a, The same reaction carried out with methylhydrazine led to a mixture of 6-(1'-methylpyrazol-3'-yl)-7-oxo- 6a,b and 6-(1'-methylpyrazol-5'-yl)-7-oxo-4,7-dihydropyrazolo-[1,5-alpha]pyrimidine 7a,b in which the former were predominant, When the reaction was carried out in ethanol, a different regioselectivity was observed leading to the isolation of the open-chain intermediate compounds 11-13 which in turn give rise, predominantly, to the pyrazolopyrimidine derivative 7a. A reaction pathway based on the X-ray structure of compound 11 is proposed.
• Synthesis and preliminary evaluation of pyrazolo[1,5-a]pyrido[3,4-e]pyrimidin-6(7H)-ones and related compounds, as benzodiazepine receptor ligands and anticonvulsant agents
  作者：S Selleri、F Bruni、A Costanzo、G Guerrini、P Malmberg Aiello、G Iavarone、C Martini

  DOI：10.1016/0223-5234(92)90033-w

  日期：1992.12