5(3)-isopropenyl-3(5)-ethoxycarbonylpyrazole | 54994-64-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 5(3)-isopropenyl-3(5)-ethoxycarbonylpyrazole
• 英文别名: 5-isopropenyl-1(2)H-pyrazole-3-carboxylic acid ethyl ester；ethyl 3-prop-1-en-2-yl-1H-pyrazole-5-carboxylate
• CAS: 54994-64-8
• 化学式: C₉H₁₂N₂O₂
• 分子量: 180.206
• InChiKey: RVXWZGFCZLLTBF-UHFFFAOYSA-N

物化性质

• 沸点：
  342.4±30.0 °C(Predicted)
• 密度：
  1.117±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  55
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  丙烯酸乙酯 、 N-(2-methylidenecyclopropyl)-N-nitrosourea 在 potassium carbonate 作用下， 以 二氯甲烷 为溶剂， 反应 2.5h， 以62%的产率得到5(3)-isopropenyl-3(5)-ethoxycarbonylpyrazole
  参考文献：
  名称：

  摘要：

  N-(1,3,3-Trideuterio-2-methylidenecyclopropyl)-N-nitrosourea was synthesized and its decomposition on treatment with K2CO3 in the presence of acrylonitrile and ethyl acrylate or on treatment with MeONa in the absence of unsaturated substrates was studied. The rate of decomposition of the nitrosourea is much lower than that of the nondeuterated analog. The use of acrylates for trapping the intermediate 3,3-dideuterio-1-diazo-2-methylidenecyclopropane results in the corresponding 2'-methylidenespiro[4,5-dihydropyrazole-5,1'-cyclopropanes] containing two deuterium atoms in the cyclopropane fragment. The resulting dihydropyrazoles are isomerized almost entirely over a period of 1-3 days to give a mixture (similar to1 : 1) of isopropenylpyrazoles in which both deuterium atoms occur either in the methyl or in the methylidene groups of the isopropenyl substituent. A possible mechanism of this transformation is considered.

  DOI：

  10.1023/a:1023910923663