ethyl 4-(4-cyanobenzyl)-3-oxo-3,4-dihydro-2H-1,4-benzoxazine-2-carboxylate | 365541-58-8

• 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-(4-cyanobenzyl)-3-oxo-3,4-dihydro-2H-1,4-benzoxazine-2-carboxylate
• 英文别名: Ethyl 4-[(4-cyanophenyl)methyl]-3-oxo-1,4-benzoxazine-2-carboxylate；ethyl 4-[(4-cyanophenyl)methyl]-3-oxo-1,4-benzoxazine-2-carboxylate
• CAS: 365541-58-8
• 化学式: C₁₉H₁₆N₂O₄
• 分子量: 336.347
• InChiKey: LHTKXDVAQWXKTE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  25
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  79.6
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  ethyl 4-(4-cyanobenzyl)-3-oxo-3,4-dihydro-2H-1,4-benzoxazine-2-carboxylate 在 sodium hydride 作用下， 以 1,4-二氧六环 为溶剂， 反应 5.0h， 生成 ethyl 4-(4-cyanobenzyl)-2-hydroxy-3-oxo-3,4-dihydro-2H-1,4-benzoxazine-2-carboxylate
  参考文献：
  名称：

  A synthesis of alkyl 4-alkyl-2-hydroxy-3-oxo-3,4-dihydro-2H-1,4-benzoxazine-2-carboxylates

  摘要：

  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.

  DOI：

  10.1016/s0040-4039(01)00954-6
• 作为产物：
  描述：

  ethyl 3-oxo-3,4-dihydro-2H-1,4-benzoxazine-2-carboxylate 、 对氰基溴化苄 在 苄基三乙基氯化铵 、 potassium carbonate 作用下， 以 乙腈 为溶剂， 以20%的产率得到ethyl 4-(4-cyanobenzyl)-3-oxo-3,4-dihydro-2H-1,4-benzoxazine-2-carboxylate
  参考文献：
  名称：

  A synthesis of alkyl 4-alkyl-2-hydroxy-3-oxo-3,4-dihydro-2H-1,4-benzoxazine-2-carboxylates

  摘要：

  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.

  DOI：

  10.1016/s0040-4039(01)00954-6

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.