8-(4,6-dimethoxypyrimidin-2-yloxy)-4-methylphthalazin-1(2H)-one | 917376-27-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 英文名称: 8-(4,6-dimethoxypyrimidin-2-yloxy)-4-methylphthalazin-1(2H)-one
• 英文别名: 8-(4,6-dimethoxypyrimidin-2-yl)oxy-4-methyl-2H-phthalazin-1-one
• CAS: 917376-27-3
• 化学式: C₁₅H₁₄N₄O₄
• 分子量: 314.301
• InChiKey: ZDKXJFILVZYXOD-UHFFFAOYSA-N

物化性质

• 熔点：
  225-227 °C
• 密度：
  1.41±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  94.9
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  8-(4,6-dimethoxypyrimidin-2-yloxy)-4-methylphthalazin-1(2H)-one 、 alkaline earth salt of/the/ methylsulfuric acid 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.5h， 以86%的产率得到2-[(2,6-Difluorophenyl)methyl]-8-(4,6-dimethoxypyrimidin-2-yl)oxy-4-methylphthalazin-1-one
  参考文献：
  名称：

  Design and Syntheses of Novel Phthalazin-1(2H)-one Derivatives as Acetohydroxyacid Synthase Inhibitors

  摘要：

  A series of 2-substituted-8-(4,6-dimethoxypyrimidin-2-yloxy)-4-methylphthalazin-1-one derivatives, 7a-7w, were designed via an ortho-substituent cyclization strategy to discover a new herbicidal lead structure. These compounds were synthesized by a seven-step route using 3-hydroxy-acetophenone as a starting material. Determination of the K-i values against wild-type A. thaliana acetohydroxyacid synthase (AHAS) (EC 4.1.3.18) indicated that some of the compounds displayed good enzyme inhibition activity comparable to that of KIH-6127. The further preliminary bioassay data on weeds showed that the synthesized compounds exhibited typical injury symptoms of AHAS-inhibiting herbicides, and some of them showed broad-spectrum and high herbicidal activities in postemergence treatments against Echinochloa crusgalli, Digitaria sanguinalis, Setaria viridis, Brassica juncea, Amaranthus retroflexus, and Chenopodium album at an application rate of 150 g ai/ha. To our knowledge, this is the first report of methylphthalazin-1-one derivatives as AHAS inhibitors.

  DOI：

  10.1021/jf061976j
• 作为产物：
  描述：

  3-苄氧基苯乙酮 在 palladium on activated charcoal 正丁基锂 、 盐酸肼 、 氢气 、 potassium carbonate 、 对甲苯磺酸 、 原甲酸三乙酯 作用下， 以 甲醇 、 正己烷 、 乙酸乙酯 、 丙酮 、 甲苯 为溶剂， 反应 37.0h， 生成 8-(4,6-dimethoxypyrimidin-2-yloxy)-4-methylphthalazin-1(2H)-one
  参考文献：
  名称：

  Design and Syntheses of Novel Phthalazin-1(2H)-one Derivatives as Acetohydroxyacid Synthase Inhibitors

  摘要：

  A series of 2-substituted-8-(4,6-dimethoxypyrimidin-2-yloxy)-4-methylphthalazin-1-one derivatives, 7a-7w, were designed via an ortho-substituent cyclization strategy to discover a new herbicidal lead structure. These compounds were synthesized by a seven-step route using 3-hydroxy-acetophenone as a starting material. Determination of the K-i values against wild-type A. thaliana acetohydroxyacid synthase (AHAS) (EC 4.1.3.18) indicated that some of the compounds displayed good enzyme inhibition activity comparable to that of KIH-6127. The further preliminary bioassay data on weeds showed that the synthesized compounds exhibited typical injury symptoms of AHAS-inhibiting herbicides, and some of them showed broad-spectrum and high herbicidal activities in postemergence treatments against Echinochloa crusgalli, Digitaria sanguinalis, Setaria viridis, Brassica juncea, Amaranthus retroflexus, and Chenopodium album at an application rate of 150 g ai/ha. To our knowledge, this is the first report of methylphthalazin-1-one derivatives as AHAS inhibitors.

  DOI：

  10.1021/jf061976j

文献信息

• Design and Syntheses of Novel Phthalazin-1(2<i>H</i>)-one Derivatives as Acetohydroxyacid Synthase Inhibitors
  作者：Yuan-Xiang Li、Yan-Ping Luo、Zhen Xi、Congwei Niu、Yan-Zhen He、Guang-Fu Yang

  DOI：10.1021/jf061976j

  日期：2006.11.1

  A series of 2-substituted-8-(4,6-dimethoxypyrimidin-2-yloxy)-4-methylphthalazin-1-one derivatives, 7a-7w, were designed via an ortho-substituent cyclization strategy to discover a new herbicidal lead structure. These compounds were synthesized by a seven-step route using 3-hydroxy-acetophenone as a starting material. Determination of the K-i values against wild-type A. thaliana acetohydroxyacid synthase (AHAS) (EC 4.1.3.18) indicated that some of the compounds displayed good enzyme inhibition activity comparable to that of KIH-6127. The further preliminary bioassay data on weeds showed that the synthesized compounds exhibited typical injury symptoms of AHAS-inhibiting herbicides, and some of them showed broad-spectrum and high herbicidal activities in postemergence treatments against Echinochloa crusgalli, Digitaria sanguinalis, Setaria viridis, Brassica juncea, Amaranthus retroflexus, and Chenopodium album at an application rate of 150 g ai/ha. To our knowledge, this is the first report of methylphthalazin-1-one derivatives as AHAS inhibitors.