4-acetyl-3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazine-3-nitrile | 882984-51-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-acetyl-3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazine-3-nitrile
• 英文别名: 4-Acetyl-2,3-dihydropyrido[3,2-b][1,4]oxazine-3-carbonitrile；4-acetyl-2,3-dihydropyrido[3,2-b][1,4]oxazine-3-carbonitrile
• CAS: 882984-51-2
• 化学式: C₁₀H₉N₃O₂
• 分子量: 203.2
• InChiKey: LXEDDMBBDKADET-UHFFFAOYSA-N

物化性质

• 熔点：
  110-112 °C
• 沸点：
  522.1±50.0 °C(Predicted)
• 密度：
  1.35±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  15
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  66.2
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-acetyl-3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazine-3-nitrile 在 N-溴代丁二酰亚胺(NBS) 、 偶氮二异丁腈 、 sodium iodide 作用下， 以 四氯化碳 、 丙酮 为溶剂， 反应 25.0h， 生成 4-acetyl-4H-pyrido[3,2-b][1,4]oxazine-3-nitrile
  参考文献：
  名称：

  Synthesis of substituted 3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazine as new scaffolds for potential bioactive compounds

  摘要：

  The title compounds having different substituents on the heterocyclic framework were prepared by several methods from 2-acetamido-3-hydroxypyridine. The condensation of 2-protected-amino-3-hydroxypyridine with 2-chloroacrylonitrile or ethyl 2,3-dibromopropionate provided in several cases two isomeric pyrido-oxazines. Whereas the reaction of 2-acetamido-3-hydroxypyridine with methyl 2,3-dibromopropionate or with alpha-halocarbonyl compounds gave exclusively the 2-substituted pyrido-oxazine, in a one-step operation. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2005.11.071
• 作为产物：
  描述：

  2-氨基-3-羟基吡啶 在 potassium carbonate 、 三乙胺 作用下， 以 二氯甲烷 、 丙酮 为溶剂， 反应 36.25h， 生成 4-acetyl-3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazine-3-nitrile
  参考文献：
  名称：

  Synthesis of substituted 3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazine as new scaffolds for potential bioactive compounds

  摘要：

  The title compounds having different substituents on the heterocyclic framework were prepared by several methods from 2-acetamido-3-hydroxypyridine. The condensation of 2-protected-amino-3-hydroxypyridine with 2-chloroacrylonitrile or ethyl 2,3-dibromopropionate provided in several cases two isomeric pyrido-oxazines. Whereas the reaction of 2-acetamido-3-hydroxypyridine with methyl 2,3-dibromopropionate or with alpha-halocarbonyl compounds gave exclusively the 2-substituted pyrido-oxazine, in a one-step operation. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2005.11.071

文献信息

• Synthesis of substituted 3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazine as new scaffolds for potential bioactive compounds
  作者：N. Henry、I. Sánchez、A. Sabatié、V. Bénéteau、G. Guillaumet、M.D. Pujol

  DOI：10.1016/j.tet.2005.11.071

  日期：2006.3

  The title compounds having different substituents on the heterocyclic framework were prepared by several methods from 2-acetamido-3-hydroxypyridine. The condensation of 2-protected-amino-3-hydroxypyridine with 2-chloroacrylonitrile or ethyl 2,3-dibromopropionate provided in several cases two isomeric pyrido-oxazines. Whereas the reaction of 2-acetamido-3-hydroxypyridine with methyl 2,3-dibromopropionate or with alpha-halocarbonyl compounds gave exclusively the 2-substituted pyrido-oxazine, in a one-step operation. (c) 2005 Elsevier Ltd. All rights reserved.