1-(2-二甲基氨基甲基-4-甲氧基苯基)-乙酮 | 77973-25-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 1-(2-二甲基氨基甲基-4-甲氧基苯基)-乙酮
• 英文名称: 1-(2-dimethylaminomethyl-4-methoxyphenyl)ethanone
• 英文别名: 1-(2-((Dimethylamino)methyl)-4-methoxyphenyl)ethanone；1-[2-[(dimethylamino)methyl]-4-methoxyphenyl]ethanone
• CAS: 77973-25-2
• 化学式: C₁₂H₁₇NO₂
• 分子量: 207.272
• InChiKey: KLUFOYLIBGBURX-UHFFFAOYSA-N

物化性质

• 沸点：
  314.8±32.0 °C(Predicted)
• 密度：
  1.028±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  3

安全信息

• 海关编码：
  2922509090
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335

反应信息

• 作为反应物：
  描述：

  4-(2-dimethylamino-ethoxy)-3',5'-dimethyl-biphenyl-3-carbaldehyde 、 1-(2-二甲基氨基甲基-4-甲氧基苯基)-乙酮 在 sodium hydroxide 作用下， 以 乙醇 为溶剂， 反应 18.0h， 以48%的产率得到(E)-3-[4-(2-dimethylamino-ethoxy)-3',5'-dimethyl-biphenyl-3-yl]-1-(2-dimethylaminomethyl-4-methoxy-phenyl)-propenone
  参考文献：
  名称：

  Cationic Chalcone Antibiotics. Design, Synthesis, and Mechanism of Action

  摘要：

  This paper describes how the introduction of "cationic" aliphatic amino groups in the chalcone scaffold results in potent antibacterial compounds. It is shown that the most favorable position for the aliphatic amino group is the 2-position of the B-ring, in particular in combination with a lipophilic substituent in the 5-position of the beta-ring. We demonstrate that the compounds act by unselective disruption of cell membranes. Introduction of an additional aliphatic amino group in the A-ring results in compounds that are selective for bacterial membranes combined with a high antibacterial activity against both Gram-positive and -negative pathogens. The most potent compound in this study (78) has an MIC value of 2 mu M against methicillin resistant Staphylococus aureus.

  DOI：

  10.1021/jm049424k
• 作为产物：
  描述：

  2-溴-5-甲氧基苯甲酰氯 在 palladium diacetate 、 1,3-双(二苯基膦)丙烷 、 硼烷 、 potassium carbonate 作用下， 以 四氢呋喃 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 7.0h， 生成 1-(2-二甲基氨基甲基-4-甲氧基苯基)-乙酮
  参考文献：
  名称：

  Cationic Chalcone Antibiotics. Design, Synthesis, and Mechanism of Action

  摘要：

  This paper describes how the introduction of "cationic" aliphatic amino groups in the chalcone scaffold results in potent antibacterial compounds. It is shown that the most favorable position for the aliphatic amino group is the 2-position of the B-ring, in particular in combination with a lipophilic substituent in the 5-position of the beta-ring. We demonstrate that the compounds act by unselective disruption of cell membranes. Introduction of an additional aliphatic amino group in the A-ring results in compounds that are selective for bacterial membranes combined with a high antibacterial activity against both Gram-positive and -negative pathogens. The most potent compound in this study (78) has an MIC value of 2 mu M against methicillin resistant Staphylococus aureus.

  DOI：

  10.1021/jm049424k

文献信息

• A new regiospecific synthesis of aryl ketones from palladocycles
  作者：R.A. Holton、K.J. Natalie

  DOI：10.1016/0040-4039(81)80072-x

  日期：1981.1

  Aromatic palladocycles undergo facile reaction with acid halides to reglospecifically provide aryl ketones In high yield.

  芳香族帕拉多环与酰卤易于反应，从而以高收率再配位性地提供芳基酮。
• Cationic Chalcone Antibiotics. Design, Synthesis, and Mechanism of Action
  作者：Simon F. Nielsen、Mogens Larsen、Thomas Boesen、Kristian Schønning、Hasse Kromann

  DOI：10.1021/jm049424k

  日期：2005.4.1

  This paper describes how the introduction of "cationic" aliphatic amino groups in the chalcone scaffold results in potent antibacterial compounds. It is shown that the most favorable position for the aliphatic amino group is the 2-position of the B-ring, in particular in combination with a lipophilic substituent in the 5-position of the beta-ring. We demonstrate that the compounds act by unselective disruption of cell membranes. Introduction of an additional aliphatic amino group in the A-ring results in compounds that are selective for bacterial membranes combined with a high antibacterial activity against both Gram-positive and -negative pathogens. The most potent compound in this study (78) has an MIC value of 2 mu M against methicillin resistant Staphylococus aureus.