2-Prop-2-ynylamino-benzooxazole-5-carbonitrile | 177268-17-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并恶唑类
• 英文名称: 2-Prop-2-ynylamino-benzooxazole-5-carbonitrile
• 英文别名: 2-(Prop-2-ynylamino)-1,3-benzoxazole-5-carbonitrile
• CAS: 177268-17-6
• 化学式: C₁₁H₇N₃O
• 分子量: 197.196
• InChiKey: OZXQQIMIQOMLOR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  61.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-Prop-2-ynylamino-benzooxazole-5-carbonitrile 在 silver tetrafluoroborate 作用下， 以 氘代乙腈 为溶剂， 生成 2H-9-Oxa-1,4a-diaza-fluorene-6-carbonitrile
  参考文献：
  名称：

  Facile Rearrangements of Alkynylamino Heterocycles with Noble Metal Cations

  摘要：

  A number of 2-(alkynylamino)-substituted heterocycles have been synthesized. These heterocycles rearrange in the presence of silver(I) and gold(I) salts to give novel 2H-pyrimido[2,1-b]benzoxazoles, 2H-pyrimido[2,1-b]benzothiazoles, and a 2H-pyrimido[2,1-b]benzoselenazole. Two of the the 2H-pyrimido[2,1-b]benzoxazoles were isolated in good yield. The kinetics of the silver tetrafluoroborate-catalyzed rearrangements of selected (alkynylamino)benzoxazoles and benzothiazoles have been examined by H-1 NMR in CD3CN. Factors affecting the electron densities of the triple bond and of the nitrogen atom in the heterocycle are important in influencing the rate of rearrangement.

  DOI：

  10.1021/jo952101z
• 作为产物：
  描述：

  4-羟基苯甲腈 在 palladium on activated charcoal 吡啶 、 氯化亚砜 、 氢气 、 硝酸 、 溶剂黄146 、 三乙胺 、 N,N-二甲基甲酰胺 作用下， 以 乙醇 、 乙酸乙酯 、 乙腈 为溶剂， 反应 3.33h， 生成 2-Prop-2-ynylamino-benzooxazole-5-carbonitrile
  参考文献：
  名称：

  Facile Rearrangements of Alkynylamino Heterocycles with Noble Metal Cations

  摘要：

  A number of 2-(alkynylamino)-substituted heterocycles have been synthesized. These heterocycles rearrange in the presence of silver(I) and gold(I) salts to give novel 2H-pyrimido[2,1-b]benzoxazoles, 2H-pyrimido[2,1-b]benzothiazoles, and a 2H-pyrimido[2,1-b]benzoselenazole. Two of the the 2H-pyrimido[2,1-b]benzoxazoles were isolated in good yield. The kinetics of the silver tetrafluoroborate-catalyzed rearrangements of selected (alkynylamino)benzoxazoles and benzothiazoles have been examined by H-1 NMR in CD3CN. Factors affecting the electron densities of the triple bond and of the nitrogen atom in the heterocycle are important in influencing the rate of rearrangement.

  DOI：

  10.1021/jo952101z