ethyl 5-oxo-2,5-dihydro-1H-azepine-3-carboxylate | 1253040-25-3

• 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-2,5-dihydro-1H-azepine-3-carboxylate
• 英文别名: Ethyl 5-oxo-1,2-dihydroazepine-3-carboxylate；ethyl 5-oxo-1,2-dihydroazepine-3-carboxylate
• CAS: 1253040-25-3
• 化学式: C₉H₁₁NO₃
• 分子量: 181.191
• InChiKey: ITPUJAXOVJVCKD-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：

  ethyl 5-oxo-2,5-dihydro-1H-azepine-3-carboxylate 在 碳酸氢钠 、 potassium carbonate 、 间氯过氧苯甲酸 作用下， 以 二氯甲烷 、 水 、 二甲基亚砜 为溶剂， 反应 16.0h， 生成 ethyl 1-allyl-5-oxo-4,5-dihydro-1H-pyrrole-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：

  1-甲氧基-3-三甲基硅氧基-1,3-丁二烯 、 ethyl 2-azidoacrylate 在 silica gel 作用下， 以 二氯甲烷 为溶剂， 反应 19.92h， 以45%的产率得到ethyl 5-oxo-2,5-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.