methyl 2-(4,6-dimethoxypyrimidin-2-yloxy)-6-(2-methyl-1,3-dioxolan-2-yl)benzoate | 150314-88-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 2-(4,6-dimethoxypyrimidin-2-yloxy)-6-(2-methyl-1,3-dioxolan-2-yl)benzoate
• CAS: 150314-88-8
• 化学式: C₁₈H₂₀N₂O₇
• 分子量: 376.366
• InChiKey: BFBPGEAYUVBIMQ-UHFFFAOYSA-N

物化性质

• 熔点：
  131-133 °C
• 沸点：
  567.7±60.0 °C(Predicted)
• 密度：
  1.270±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.29
• 重原子数：
  27.0
• 可旋转键数：
  6.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  98.23
• 氢给体数：
  0.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  methyl 2-(4,6-dimethoxypyrimidin-2-yloxy)-6-(2-methyl-1,3-dioxolan-2-yl)benzoate 在 盐酸肼 、 sodium hydride 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 24.5h， 生成 8-(4,6-Dimethoxypyrimidin-2-yl)oxy-2-[(3-fluorophenyl)methyl]-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-羟基苯乙酮 在 palladium on activated charcoal 正丁基锂 、 氢气 、 potassium carbonate 、 对甲苯磺酸 、 原甲酸三乙酯 作用下， 以 正己烷 、 乙酸乙酯 、 丙酮 、 甲苯 、 乙腈 为溶剂， 反应 16.0h， 生成 methyl 2-(4,6-dimethoxypyrimidin-2-yloxy)-6-(2-methyl-1,3-dioxolan-2-yl)benzoate
  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