2-chloro-N-(N-oxide-pyridin-4-ylmethyl)acetamide | 1415817-93-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 2-chloro-N-(N-oxide-pyridin-4-ylmethyl)acetamide
• 英文别名: 2-chloro-N-[(1-oxidopyridin-1-ium-4-yl)methyl]acetamide
• CAS: 1415817-93-4
• 化学式: C₈H₉ClN₂O₂
• 分子量: 200.625
• InChiKey: LNMNVQPLHFLHSR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.4
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  54.6
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-chloro-N-(N-oxide-pyridin-4-ylmethyl)acetamide 在 六氟磷酸钾 作用下， 以 乙醇 、 水 为溶剂， 反应 35.0h， 生成 1-methyl-3-(2-oxo-2-(N-(N-oxide-pyridin-4-ylmethyl))-ylamine)ethyl-imidazolium hexafluorophosphate
  参考文献：
  名称：

  Methyltrioxorhenium-catalyzed epoxidation of olefins with hydrogen peroxide as an oxidant and pyridine N-oxide ionic liquids as additives

  摘要：

  Four ionic liquids (ILs) with both a pyridine N-oxide moiety and an imidazolium moiety combined by an amide spacer were synthesized through a series of reactions including amidation, peroxidation, quaterization and anion exchange reaction. Their structures were fully characterized by H-1 NMR, FT-IR, UV-vis and HR-MS. The ionic liquids were used respectively as additives in the methyltrioxorhenium (MTO) catalyzed epoxidation of olefins with 30% H2O2 as an oxidant. The catalytic results displayed that the ILs had excellent performances in suppressing epoxide ring-opening reaction, which led to the significant improvement of the selectivity of the MTO-catalyzed epoxidation with low loadings compared to other substances as additives. The coexistence of the pyridine N-oxide and imidazolium moieties in the structures of ILs is necessary in improving the MTO-catalyzed epoxidation reaction. It was also displayed that the improvement degree on the selectivity of epoxidation depended on the type of anion of the ILs, but not the position of the substituent with imidazolium moiety in the ring of pyridine N-oxide. Meanwhile, the results also showed that the introduction of the ILs caused the decrease of the epoxidation rate, but this side effect was small compared to those of other substances used as additives. (c) 2012 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.molcata.2012.09.017
• 作为产物：
  描述：

  2-chloro-N-(pyridin-4-ylmethyl)acetamide 在 双氧水 、 溶剂黄146 、 尿素 作用下， 反应 10.0h， 生成 2-chloro-N-(N-oxide-pyridin-4-ylmethyl)acetamide
  参考文献：
  名称：

  Methyltrioxorhenium-catalyzed epoxidation of olefins with hydrogen peroxide as an oxidant and pyridine N-oxide ionic liquids as additives

  摘要：

  Four ionic liquids (ILs) with both a pyridine N-oxide moiety and an imidazolium moiety combined by an amide spacer were synthesized through a series of reactions including amidation, peroxidation, quaterization and anion exchange reaction. Their structures were fully characterized by H-1 NMR, FT-IR, UV-vis and HR-MS. The ionic liquids were used respectively as additives in the methyltrioxorhenium (MTO) catalyzed epoxidation of olefins with 30% H2O2 as an oxidant. The catalytic results displayed that the ILs had excellent performances in suppressing epoxide ring-opening reaction, which led to the significant improvement of the selectivity of the MTO-catalyzed epoxidation with low loadings compared to other substances as additives. The coexistence of the pyridine N-oxide and imidazolium moieties in the structures of ILs is necessary in improving the MTO-catalyzed epoxidation reaction. It was also displayed that the improvement degree on the selectivity of epoxidation depended on the type of anion of the ILs, but not the position of the substituent with imidazolium moiety in the ring of pyridine N-oxide. Meanwhile, the results also showed that the introduction of the ILs caused the decrease of the epoxidation rate, but this side effect was small compared to those of other substances used as additives. (c) 2012 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.molcata.2012.09.017