4-Oxo-5,6,7,8-tetrahydro-4H-cyclohepta[b]furan-3-carboxylic acid (2-fluoro-4-methoxy-phenyl)-amide | 225240-81-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 4-Oxo-5,6,7,8-tetrahydro-4H-cyclohepta[b]furan-3-carboxylic acid (2-fluoro-4-methoxy-phenyl)-amide
• 英文别名: N-(2-Fluoro-4-methoxyphenyl)-4-oxo-5,6,7,8-tetrahydro-4H-cyclohepta[b]furan-3-carboxamide；N-(2-fluoro-4-methoxyphenyl)-4-oxo-5,6,7,8-tetrahydrocyclohepta[b]furan-3-carboxamide
• CAS: 225240-81-3
• 化学式: C₁₇H₁₆FNO₄
• 分子量: 317.317
• InChiKey: QOBQEJNQDPECSX-UHFFFAOYSA-N

物化性质

• 沸点：
  411.3±45.0 °C(Predicted)
• 密度：
  1.320±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  23
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  68.5
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4-Oxo-5,6,7,8-tetrahydro-4H-cyclohepta[b]furan-3-carboxylic acid (2-fluoro-4-methoxy-phenyl)-amide 在 N-甲基吡咯烷酮 、 ammonium acetate 作用下， 反应 24.0h， 以43%的产率得到4-oxo-1,4,5,6,7,8-hexahydrocyclohepta[b]pyrrole-3-carboxylic acid (2-fluoro-4-methoxyphenyl)amide
  参考文献：
  名称：

  Structural Determination of a Process Impurity in a Furan−Pyrrole Heteroatom Exchange Reaction

  摘要：

  Electron-deficient pyrrole (1) was derivatized by diazotization with p-nitrobenzene diazonium chloride. Reduction of the diazo intermediates gave 2- and 1-aminopyrroles (3 and 4). The 2-aminopyrrole (3) was determined to be the process impurity formed during a furan-pyrrole heteroatom exchange reaction. An oxidative mechanism for the impurity formation was hypothesized. Nitrogen sparging of the reaction mixture prior to heating eliminated formation of 3.

  DOI：

  10.1021/op010227u
• 作为产物：
  描述：

  呋喃 、 糠酰胺 、 甲基叔丁基醚 、 2-氟-4-甲氧基苯胺 、 氯甲酸乙酯 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 生成 4-Oxo-5,6,7,8-tetrahydro-4H-cyclohepta[b]furan-3-carboxylic acid (2-fluoro-4-methoxy-phenyl)-amide
  参考文献：
  名称：

  Method of synthesis of pyrrole amides

  摘要：

  一种制备选择性结合到GABAa受体的吡咯羧酰胺的方法；包括将1,3-环戊二酮与溴乙醋酸酯反应，然后将生成的产物与酸卤化物反应，再与芳香胺反应，最后在高温下与铵源反应。

  公开号：

  US06262272B1

文献信息

• Method of synthesis of pyrrole amides
  申请人：Pfizer Inc

  公开号：US06262272B1

  公开（公告）日：2001-07-17

  A method for preparing pyrrole-carboxyamides which selectively bind to GABAa receptors; which comprises reacting 1,3-cycloakane-diones with bromoethylacetate followed by reaction of the resulting product with an acid halide followed by reaction with an aromatic amine and finally with an amonium source at an elevated temperature.

  一种制备选择性结合到GABAa受体的吡咯羧酰胺的方法；包括将1,3-环戊二酮与溴乙醋酸酯反应，然后将生成的产物与酸卤化物反应，再与芳香胺反应，最后在高温下与铵源反应。
• Structural Determination of a Process Impurity in a Furan−Pyrrole Heteroatom Exchange Reaction
  作者：Bryan Li、Narasimhan Kasthurikrishnan、John A. Ragan、Gregory R. Young

  DOI：10.1021/op010227u

  日期：2002.1.1

  Electron-deficient pyrrole (1) was derivatized by diazotization with p-nitrobenzene diazonium chloride. Reduction of the diazo intermediates gave 2- and 1-aminopyrroles (3 and 4). The 2-aminopyrrole (3) was determined to be the process impurity formed during a furan-pyrrole heteroatom exchange reaction. An oxidative mechanism for the impurity formation was hypothesized. Nitrogen sparging of the reaction mixture prior to heating eliminated formation of 3.