2-hydroxy-5-(1H-imidazol-1-ylmethyl)acetophenone | 136081-33-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-hydroxy-5-(1H-imidazol-1-ylmethyl)acetophenone
• 英文别名: 1-[(3-Acetyl-4-hydroxyphenyl)methyl]imidazole；1-[2-hydroxy-5-(imidazol-1-ylmethyl)phenyl]ethanone
• CAS: 136081-33-9
• 化学式: C₁₂H₁₂N₂O₂
• 分子量: 216.239
• InChiKey: NDINXRQICVQLLH-UHFFFAOYSA-N

物化性质

• 沸点：
  432.5±35.0 °C(Predicted)
• 密度：
  1.21±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  55.1
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-hydroxy-5-(1H-imidazol-1-ylmethyl)acetophenone 、 4-异丙基苯甲醛 在 potassium hydroxide 作用下， 以 乙醇 为溶剂， 反应 24.0h， 以63%的产率得到(E)-1-[2-hydroxy-5-(1H-imidazol-1-ylmethyl)-phenyl]-3-(4-isopropylphenyl)prop-2-en-1-one
  参考文献：
  名称：

  Synthesis and antimicrobial activity of chalcones containing benzotriazolylmethyl and imidazolylmethyl substituents

  摘要：

  Methods have been developed for the synthesis of new 1H-benzotriazol-1-ylmethyl- and 1H-imidazol-1-ylmethyl-substituted chalcones starting from 2-hydroxyacetophenone. The procedures include chloromethylation, N-alkylation, and Claisen-Schmidt condensation. The presence of an imidazole fragment on the ring A and piperazine fragment on the ring B of the resulting chalcones increases their antimicrobial activity (minimum inhibitory concentration 12.5-50.0 mu g/mL), whereas introduction of a benzotriazole fragment reduces the antimicrobial activity.

  DOI：

  10.1134/s1070428014120094
• 作为产物：
  描述：

  2'-羟基苯乙酮 在 盐酸 、 (1-丁基)三乙基溴化铵 、 potassium carbonate 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 8.33h， 生成 2-hydroxy-5-(1H-imidazol-1-ylmethyl)acetophenone
  参考文献：
  名称：

  Synthesis and antimicrobial activity of chalcones containing benzotriazolylmethyl and imidazolylmethyl substituents

  摘要：

  Methods have been developed for the synthesis of new 1H-benzotriazol-1-ylmethyl- and 1H-imidazol-1-ylmethyl-substituted chalcones starting from 2-hydroxyacetophenone. The procedures include chloromethylation, N-alkylation, and Claisen-Schmidt condensation. The presence of an imidazole fragment on the ring A and piperazine fragment on the ring B of the resulting chalcones increases their antimicrobial activity (minimum inhibitory concentration 12.5-50.0 mu g/mL), whereas introduction of a benzotriazole fragment reduces the antimicrobial activity.

  DOI：

  10.1134/s1070428014120094

文献信息

• Nitrogen-containing spirocycles
  申请人：Merck & Co., Inc.

  公开号：US05206240A1

  公开（公告）日：1993-04-27

  Spirocycles of general structural formula: ##STR1## are Class III antiarrhythmic agents.

  通用结构式为：##STR1## 的螺环化合物是III类抗心律失常药物。
• Spiro(pyran)piperidine derivatives
  申请人：Merck & Co., Inc.

  公开号：EP0431943B1

  公开（公告）日：1998-07-15
• US5206240A
  申请人：——

  公开号：US5206240A

  公开（公告）日：1993-04-27
• US5633247A
  申请人：——

  公开号：US5633247A

  公开（公告）日：1997-05-27
• Synthesis and antimicrobial activity of chalcones containing benzotriazolylmethyl and imidazolylmethyl substituents
  作者：L. V. Chinh、T. N. Hung、N. T. Nga、T. T. N. Hang、T. T. N. Mai、V. A. Tarasevich

  DOI：10.1134/s1070428014120094

  日期：2014.12

  Methods have been developed for the synthesis of new 1H-benzotriazol-1-ylmethyl- and 1H-imidazol-1-ylmethyl-substituted chalcones starting from 2-hydroxyacetophenone. The procedures include chloromethylation, N-alkylation, and Claisen-Schmidt condensation. The presence of an imidazole fragment on the ring A and piperazine fragment on the ring B of the resulting chalcones increases their antimicrobial activity (minimum inhibitory concentration 12.5-50.0 mu g/mL), whereas introduction of a benzotriazole fragment reduces the antimicrobial activity.