ethyl 4-methyl-3-oxo-3,4-dihydro-2H-1,4-benzoxazine-2-carboxylate | 211994-50-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并恶嗪类
• 英文名称: ethyl 4-methyl-3-oxo-3,4-dihydro-2H-1,4-benzoxazine-2-carboxylate
• 英文别名: Ethyl 4-methyl-3-oxo-1,4-benzoxazine-2-carboxylate
• CAS: 211994-50-2
• 化学式: C₁₂H₁₃NO₄
• 分子量: 235.24
• InChiKey: HTHWMMMCFQDZCT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  55.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  ethyl 4-methyl-3-oxo-3,4-dihydro-2H-1,4-benzoxazine-2-carboxylate 在 potassium fluoride 、 sodium hydroxide 作用下， 以 1,4-二氧六环 、 N,N-二甲基甲酰胺 为溶剂， 反应 72.0h， 生成 benzyl 4-methyl-3-oxo-3,4-dihydro-2H-1,4-benzoxazine-2-carboxylate
  参考文献：
  名称：

  Selective Alkylation of 3-Oxo-3,4-Dihydro-2H-1,4-Benzoxazine-2-Carboxylates

  摘要：

  Selective N-alkylation of 3-oxo-3,4-dihydro-2H-1,4-benzoxazine-2-carboxylates is achieved under phase transfer catalysis. Alkylation of 4-alkyl-3-oxo-3,4-dihydro-2H-l,4-benzoxazine-2-carboxylates at position 2 using sodium hydride as a base affords 2,4-dialkyl-3-oxo-3,4-dihydro-2H- 1,4-benzoxazine-2-carboxylates.

  DOI：

  10.1080/00397919808004847
• 作为产物：
  描述：

  溴代丙二酸二乙酯 在 palladium on activated charcoal 、 苄基三乙基氯化铵 potassium fluoride 、 氢气 、 potassium carbonate 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 14.0h， 生成 ethyl 4-methyl-3-oxo-3,4-dihydro-2H-1,4-benzoxazine-2-carboxylate
  参考文献：
  名称：

  Selective Alkylation of 3-Oxo-3,4-Dihydro-2H-1,4-Benzoxazine-2-Carboxylates

  摘要：

  Selective N-alkylation of 3-oxo-3,4-dihydro-2H-1,4-benzoxazine-2-carboxylates is achieved under phase transfer catalysis. Alkylation of 4-alkyl-3-oxo-3,4-dihydro-2H-l,4-benzoxazine-2-carboxylates at position 2 using sodium hydride as a base affords 2,4-dialkyl-3-oxo-3,4-dihydro-2H- 1,4-benzoxazine-2-carboxylates.

  DOI：

  10.1080/00397919808004847

文献信息

• A synthesis of alkyl 4-alkyl-2-hydroxy-3-oxo-3,4-dihydro-2H-1,4-benzoxazine-2-carboxylates
  作者：Petra Štefanič、Matej Breznik、Nina Lah、Ivan Leban、Janez Plavec、Danijel Kikelj

  DOI：10.1016/s0040-4039(01)00954-6

  日期：2001.7

  Reaction of ethyl 4-alkyl-3-oxo-3,4-dihydro-2H-1,4-benzoxazine-2-carboxylates with sodium hydride in dioxane affords ethyl 4-alkyl-2-hydroxy-3-oxo-3,4-dihydro-2H-1,4-benzoxazine-2-carboxylates. The structure of the products was unambiguously established by X-ray analysis as well as by H-1-C-13 and H-1-N-15 NMR correlation spectroscopy. (C) 2001 Published by Elsevier Science Ltd.
• Synthesis of alkyl 4-alkyl-2-hydroxy-3-oxo-3,4-dihydro-2H-1,4-benzoxazine-2-carboxylates as peptidomimetic building blocks
  作者：Petra Štefanič、Katja Turnšek、Danijel Kikelj

  DOI：10.1016/s0040-4020(03)01102-5

  日期：2003.9

  A general synthesis of new alkyl 4-alkyl-2-hydroxy-3-oxo-3,4-dihydro-2H-1,4-benzoxazine-2-carboxylate peptidomimetic building blocks from the corresponding alkyl 3-oxo-3,4-dihydro-2H-1,4-benzoxazine-2-carboxylates through carbanion oxidation is described. (C) 2003 Elsevier Ltd. All rights reserved.