2-methoxy-4-nitro-5-chloro-N-<2-diethylaminoethyl>benzamide | 22459-75-2

• 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: 2-methoxy-4-nitro-5-chloro-N-<2-diethylaminoethyl>benzamide
• 英文别名: N(2-Diethylaminoethyl)-2-methoxy-4-nitro-5-chlorbenzamid；5-Chloro-N-[2-(diethylamino)ethyl]-2-methoxy-4-nitrobenzamide；5-chloro-N-[2-(diethylamino)ethyl]-2-methoxy-4-nitrobenzamide
• CAS: 22459-75-2
• 化学式: C₁₄H₂₀ClN₃O₄
• 分子量: 329.783
• InChiKey: PVUYBBJPARWTJY-UHFFFAOYSA-N

物化性质

• 熔点：
  85 °C
• 沸点：
  449.6±45.0 °C(Predicted)
• 密度：
  1.233±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  22
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  87.4
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-methoxy-4-nitro-5-chloro-N-<2-diethylaminoethyl>benzamide 在 氯化铵 、 锌 作用下， 以 乙醇 、 水 为溶剂， 反应 0.08h， 以75%的产率得到5-chloro-N-[2-(diethylamino)ethyl]-4-(hydroxyamino)-2-methoxybenzamide
  参考文献：
  名称：

  Identification and full characterization of a new metabolite of metoclopramide

  摘要：

  The metabolism of metoclopramide 1 has been reinvestigated by HPLC coupled with mass spectrometry. The urine of healthy volunteers showed the presence of a new metabolite 2 derived from the enzymatic oxidation of the primary aromatic amino group of 1 to the hydroxylamino moiety. The structure of the new metabolite was ascertained by its fragmentation pattern in the mass spectrometer and unambiguously secured by an independent synthesis. In addition, the tertiary amine group of 1 was selectively oxidized to the corresponding N-oxide. This compound and its ring oxidation metabolites were not detected in the urine of the tested volunteers.

  DOI：

  10.1016/0223-5234(96)88294-8
• 作为产物：
  描述：

  4-氨基-5-氯-2-甲氧基苯甲酸 在 sodium perborate 、 氯化亚砜 、 溶剂黄146 作用下， 反应 4.0h， 生成 2-methoxy-4-nitro-5-chloro-N-<2-diethylaminoethyl>benzamide
  参考文献：
  名称：

  Identification and full characterization of a new metabolite of metoclopramide

  摘要：

  The metabolism of metoclopramide 1 has been reinvestigated by HPLC coupled with mass spectrometry. The urine of healthy volunteers showed the presence of a new metabolite 2 derived from the enzymatic oxidation of the primary aromatic amino group of 1 to the hydroxylamino moiety. The structure of the new metabolite was ascertained by its fragmentation pattern in the mass spectrometer and unambiguously secured by an independent synthesis. In addition, the tertiary amine group of 1 was selectively oxidized to the corresponding N-oxide. This compound and its ring oxidation metabolites were not detected in the urine of the tested volunteers.

  DOI：

  10.1016/0223-5234(96)88294-8

文献信息

• Identification and full characterization of a new metabolite of metoclopramide
  作者：V Maurich、M De Amici、C De Micheli、P Rossato

  DOI：10.1016/0223-5234(96)88294-8

  日期：1995.1

  The metabolism of metoclopramide 1 has been reinvestigated by HPLC coupled with mass spectrometry. The urine of healthy volunteers showed the presence of a new metabolite 2 derived from the enzymatic oxidation of the primary aromatic amino group of 1 to the hydroxylamino moiety. The structure of the new metabolite was ascertained by its fragmentation pattern in the mass spectrometer and unambiguously secured by an independent synthesis. In addition, the tertiary amine group of 1 was selectively oxidized to the corresponding N-oxide. This compound and its ring oxidation metabolites were not detected in the urine of the tested volunteers.