1-(5-甲基-2-丙基-1H-咪唑-4-基)乙酮 | 84227-32-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 中文名称: 1-(5-甲基-2-丙基-1H-咪唑-4-基)乙酮
• 英文名称: methyl 5-methyl-2-propyl-4-imidazolyl ketone
• 英文别名: 5-Acetyl-4-methyl-2-n-propylimidazole；1-(5-Methyl-2-propyl-1H-imidazol-4-yl)ethan-1-one；1-(5-methyl-2-propyl-1H-imidazol-4-yl)ethanone
• CAS: 84227-32-7
• 化学式: C₉H₁₄N₂O
• 分子量: 166.223
• InChiKey: WXFQRFAPEICWRJ-UHFFFAOYSA-N

物化性质

• 沸点：
  358.5±22.0 °C(Predicted)
• 密度：
  1.051±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  45.8
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-(5-甲基-2-丙基-1H-咪唑-4-基)乙酮 在 sodium hydride 、 溶剂黄146 作用下， 反应 9.25h， 生成 3-Ethyl-1,8-dimethyl-6-propylimidazo[1,5-d][1,2,4]triazin-4-one
  参考文献：
  名称：

  Imidazo[1,5-d][1,2,4]triazines as potential antiasthma agents

  摘要：

  By using inhibition of histamine release from antigen-challenged, sensitized human basophils as a means of identifying a potentially prophylactic drug for the treatment of asthma, a series of substituted imidazo[1,5-d][1,2,4]triazines were found, which were active. These compounds were prepared by treating imidazolecarboxaldehydes with excess Grignard agent and then oxidizing the resulting alcohols to ketones with Jones reagent. Pyrolysis of a mixture of ketone and methyl carbazate at 200 degrees C in diphenyl ether produced the desired imidazo[1,5-d][1,2,4]triazines. Those compounds with the greatest basophil activity were tested for in vivo activity in the mouse passive cutaneous anaphylaxis (PCA) and the guinea pig passive anaphylaxis tests. The best compounds, 1-ethyl-8-methyl-6-propylimidazo[1,5-d][1,2,4]triazin-4(3H)- one (4-17) and 1,8-dimethyl-6-propylimidazo[1,5-d][1,2,4]triazin-4-(3H)-one (4-16) were chosen for further study.

  DOI：

  10.1021/jm00149a029
• 作为产物：
  描述：

  α,5-dimethyl-2-propyl-4-imidazolemethanol 在 chromium(VI) oxide 、 硫酸 作用下， 以 水 、 丙酮 为溶剂， 反应 0.5h， 以93%的产率得到1-(5-甲基-2-丙基-1H-咪唑-4-基)乙酮
  参考文献：
  名称：

  Imidazo[1,5-d][1,2,4]triazines as potential antiasthma agents

  摘要：

  By using inhibition of histamine release from antigen-challenged, sensitized human basophils as a means of identifying a potentially prophylactic drug for the treatment of asthma, a series of substituted imidazo[1,5-d][1,2,4]triazines were found, which were active. These compounds were prepared by treating imidazolecarboxaldehydes with excess Grignard agent and then oxidizing the resulting alcohols to ketones with Jones reagent. Pyrolysis of a mixture of ketone and methyl carbazate at 200 degrees C in diphenyl ether produced the desired imidazo[1,5-d][1,2,4]triazines. Those compounds with the greatest basophil activity were tested for in vivo activity in the mouse passive cutaneous anaphylaxis (PCA) and the guinea pig passive anaphylaxis tests. The best compounds, 1-ethyl-8-methyl-6-propylimidazo[1,5-d][1,2,4]triazin-4(3H)- one (4-17) and 1,8-dimethyl-6-propylimidazo[1,5-d][1,2,4]triazin-4-(3H)-one (4-16) were chosen for further study.

  DOI：

  10.1021/jm00149a029

文献信息

• Process for preparing
  申请人：American Cyanamid Co.

  公开号：US04395547A1

  公开（公告）日：1983-07-26

  This disclosure describes a novel process for the preparation of 1-(lower alkyl)substituted derivatives of 6-n-propyl-8-alkylimidazo[1,5-d]-as-triazin-4(3H)-ones which are useful as anti-asthmatic agents.

  本公开描述了一种新颖的制备1-(较低烷基)取代的6-n-丙基-8-烷基咪唑并三唑并[1,5-d]-嘧啶-4(3H)-酮衍生物的过程，这些衍生物可用作抗哮喘药物。
• Substituted-6-n-propyl-8-methylimidazo[1,5-d]-as-triazin-4-(3H)-ones
  申请人：American Cyanamid Company

  公开号：US04447603A1

  公开（公告）日：1984-05-08

  This disclosure describes new compounds and compositions of matter useful as anti-asthmatic agents and the method of meliorating asthma in mammals therewith, the novel active ingredients of said compositions of matter being certain 1-substituted-6-n-propyl-8-methylimidazo [1,5-d]-as-triazin-4(3H)-ones and/or the pharmacologically acceptable acid-addition salts thereof.

  本公开说明了一些新的化合物和物质组成，它们可用作抗哮喘剂，并且使用这些化合物和物质组成的方法可改善哺乳动物的哮喘症状。这些物质组成的新活性成分是某些1-取代-6-正丙基-8-甲基咪唑并[1,5-d]-嘧啶-4（3H）-酮和/或其药理学上可接受的酸加成盐。
• Process for preparing 5-imidazolyl ketones
  申请人：American Cyanamid Company

  公开号：US04459413A1

  公开（公告）日：1984-07-10

  This disclosure describes a novel process for the preparation of 1-(lower alkyl)substituted derivatives of 6-n-propyl-8-alkylimidazo[1,5-d]-as-triazin-4(3H)-ones which are useful as anti-asthmatic agents.

  本公开说明了一种新的制备1-(低烷基)取代的6-丙基-8-烷基咪唑[1,5-d]-嘧啶-4(3H)-酮衍生物的过程，这些衍生物可用作抗哮喘药物。
• 1-Substituted-6-n-propyl-8-methylimidazo(1,5-d)-as-triazin-4(3H)-ones
  申请人：AMERICAN CYANAMID COMPANY

  公开号：EP0057289A1

  公开（公告）日：1982-08-11

  This disclosure describes new compounds and compositions of matter useful as anti-asthmatic agents and the method of meliorating asthma in mammals therewith, the novel active ingredients of said compositions of matter being certain 1-substituted-6-n-propyl-8-methylimidazo [1,5-d]-as-triazin-4(3H)-ones and/or the pharmacologically acceptable acid-addition salts thereof.

  本公开描述了可用作抗哮喘药的新化合物和物质组合物，以及用其改善哺乳动物哮喘的方法，所述物质组合物的新活性成分是某些 1-取代-6-正丙基-8-甲基咪唑并[1,5-d]-异三嗪-4(3H)-酮和/或其药理上可接受的酸加成盐。
• Process for preparing 1-substituted-6-n-propyl-8-methylimidazo(1,5-d)-as-triazin-4(3H)-ones
  申请人：AMERICAN CYANAMID COMPANY

  公开号：EP0085756A1

  公开（公告）日：1983-08-17

  This disclosure describes novel processes for the preparation of 2-(n-propyll-4-methyl-5-(lower alkanoyl) imidazoles which are useful as intermediates for the preparation of anti-asthmatic agents.

  本公开介绍了制备 2-(正丙基-4-甲基-5-(低级烷酰基)咪唑的新工艺，这些咪唑可用作制备抗哮喘药物的中间体。