4-ethoxycarbonyl-3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazine-3-nitrile

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-ethoxycarbonyl-3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazine-3-nitrile
• 英文别名: Ethyl 3-cyano-2,3-dihydropyrido[3,2-b][1,4]oxazine-4-carboxylate；ethyl 3-cyano-2,3-dihydropyrido[3,2-b][1,4]oxazine-4-carboxylate
• 化学式: C₁₁H₁₁N₃O₃
• 分子量: 233.227
• InChiKey: VWPDBHBIUGRIDT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  75.4
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 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 、 乙腈 为溶剂， 反应 6.25h， 生成 4-ethoxycarbonyl-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.