ethyl 5-oxo-4,5-dihydro-1H-azepine-3-carboxylate | 1253040-27-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吖庚因类
• 英文名称: ethyl 5-oxo-4,5-dihydro-1H-azepine-3-carboxylate
• 英文别名: Ethyl 5-oxo-1,4-dihydroazepine-3-carboxylate
• CAS: 1253040-27-5
• 化学式: C₉H₁₁NO₃
• 分子量: 181.191
• InChiKey: LWJJJFPVSNPKRE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  55.4
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  正溴丁烷 、 ethyl 5-oxo-4,5-dihydro-1H-azepine-3-carboxylate 在 potassium carbonate 作用下， 以 二甲基亚砜 为溶剂， 反应 24.0h， 以87%的产率得到ethyl 1-butyl-5-oxo-4,5-dihydro-1H-azepine-3-carboxylate
  参考文献：
  名称：

  Reactions of azepinones with electrophiles

  摘要：

  Azepinones are available via a one-pot cycloaddition-ring expansion reaction sequence in good yield. The reactions of azepinones with alkyl halides and epoxides were studied. We report herein protocols for the alkylation of azepinones at nitrogen with alkyl halides and epoxides and the isomerizations that occur in the presence of a base. We also report an unexpected ring contraction under oxidative conditions. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2010.12.091
• 作为产物：
  描述：

  (+/-)-(2R,6R)-ethyl 2-methoxy-4-(trimethylsilyloxy)-1-azabicyclo[4.1.0]hept-3-ene-6-carboxylate 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 以60%的产率得到ethyl 5-oxo-4,5-dihydro-1H-azepine-3-carboxylate
  参考文献：
  名称：

  On the preparation of azepinones

  摘要：

  We report here a simple and efficient preparation of 1H-azepin-5(2H)-ones and their unexpectedly facile isomerization to 1H-azepin-5(4H)-ones under mildly basic reaction conditions. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2010.08.003

文献信息

• On the preparation of azepinones
  作者：Galyna G. Dubinina、Wesley Y. Yoshida、William J. Chain

  DOI：10.1016/j.tetlet.2010.08.003

  日期：2010.10

  We report here a simple and efficient preparation of 1H-azepin-5(2H)-ones and their unexpectedly facile isomerization to 1H-azepin-5(4H)-ones under mildly basic reaction conditions. (C) 2010 Elsevier Ltd. All rights reserved.
• Reactions of azepinones with electrophiles
  作者：Galyna G. Dubinina、William J. Chain

  DOI：10.1016/j.tetlet.2010.12.091

  日期：2011.2

  Azepinones are available via a one-pot cycloaddition-ring expansion reaction sequence in good yield. The reactions of azepinones with alkyl halides and epoxides were studied. We report herein protocols for the alkylation of azepinones at nitrogen with alkyl halides and epoxides and the isomerizations that occur in the presence of a base. We also report an unexpected ring contraction under oxidative conditions. (C) 2010 Elsevier Ltd. All rights reserved.