4-benzoylamino-4-oxo-butyric acid methyl ester | 550310-34-4

• 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-benzoylamino-4-oxo-butyric acid methyl ester
• 英文别名: Methyl 4-benzamido-4-oxobutanoate
• CAS: 550310-34-4
• 化学式: C₁₂H₁₃NO₄
• 分子量: 235.24
• InChiKey: QYTYKINCMCNSQU-UHFFFAOYSA-N

物化性质

• 沸点：
  404.3±37.0 °C(Predicted)
• 密度：
  1?+-.0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  17
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  72.5
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  methyl 4-benzamidobutanoate 在 水 、 Selectfluor 、 copper(I) bromide 作用下， 以 乙腈 为溶剂， 反应 1.0h， 以82%的产率得到4-benzoylamino-4-oxo-butyric acid methyl ester
  参考文献：
  名称：

  Copper mediated oxidation of amides to imides by Selectfluor

  摘要：

  The combination of Selectfluor and copper(I) bromide has shown a strong oxidation ability, readily oxidizing amides into the corresponding imides in acetonitrile at room temperature in less than 1 h. This transformation under mild conditions gives good to excellent chemical yields. A possible reaction mechanism is proposed. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2011.02.059

文献信息

• Copper mediated oxidation of amides to imides by Selectfluor
  作者：Zhuang Jin、Bo Xu、Gerald B. Hammond

  DOI：10.1016/j.tetlet.2011.02.059

  日期：2011.4

  The combination of Selectfluor and copper(I) bromide has shown a strong oxidation ability, readily oxidizing amides into the corresponding imides in acetonitrile at room temperature in less than 1 h. This transformation under mild conditions gives good to excellent chemical yields. A possible reaction mechanism is proposed. (C) 2011 Elsevier Ltd. All rights reserved.
• Replacement of BF4− by PF6− makes Selectfluor greener
  作者：Zhuang Jin、Bo Xu、Stephen G. DiMagno、Gerald B. Hammond

  DOI：10.1016/j.jfluchem.2012.05.010

  日期：2012.11

  A combination of F-TEDA-PF6 and CuBr (0.1 equiv.) provides a potent oxidant that readily oxidizes amides to provide imides at room temperature. Replacement of BF4-, the anion of Selectfluor (F-TEDA-BF4), by PF6-, dramatically reduces CuBr loading in this oxidative reaction. A possible rationale for this dramatic counterion effect is provided. (C) 2012 Elsevier B.V. All rights reserved.