ethyl 4-ethyl-3-oxo-3,4-dihydro-2H-1,4-benzoxazine-2-carboxylate | 211994-51-3

• 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-ethyl-3-oxo-3,4-dihydro-2H-1,4-benzoxazine-2-carboxylate
• 英文别名: Ethyl 4-ethyl-3-oxo-1,4-benzoxazine-2-carboxylate
• CAS: 211994-51-3
• 化学式: C₁₃H₁₅NO₄
• 分子量: 249.266
• InChiKey: JWVZWCQUEXIWKJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 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-ethyl-3-oxo-3,4-dihydro-2H-1,4-benzoxazine-2-carboxylate 在 4 A molecular sieve 、 氧气 、 sodium hydride 作用下， 以75%的产率得到ethyl 4-ethyl-2-hydroxy-3-oxo-3,4-dihydro-2H-1,4-benzoxazine-2-carboxylate
  参考文献：
  名称：

  Synthesis of alkyl 4-alkyl-2-hydroxy-3-oxo-3,4-dihydro-2H-1,4-benzoxazine-2-carboxylates as peptidomimetic building blocks

  摘要：

  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.

  DOI：

  10.1016/s0040-4020(03)01102-5
• 作为产物：
  描述：

  diethyl 2-(2'-nitrophenoxy)malonate 在 palladium on activated charcoal 、 苄基三乙基氯化铵 氢气 、 potassium carbonate 作用下， 以 乙醇 、 乙腈 为溶剂， 反应 8.0h， 生成 ethyl 4-ethyl-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.