methyl 2-hydroxy-6-(2-methyl-1,3-dioxolan-2-yl)benzoate | 147411-62-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: methyl 2-hydroxy-6-(2-methyl-1,3-dioxolan-2-yl)benzoate
• CAS: 147411-62-9
• 化学式: C₁₂H₁₄O₅
• 分子量: 238.24
• InChiKey: KFMXAQPMUNIVDY-UHFFFAOYSA-N

物化性质

• 熔点：
  141-143 °C
• 沸点：
  360.7±42.0 °C(Predicted)
• 密度：
  1?+-.0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  65
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  methyl 2-hydroxy-6-(2-methyl-1,3-dioxolan-2-yl)benzoate 在 盐酸 、 potassium carbonate 作用下， 以 丙酮 为溶剂， 反应 10.0h， 生成 Methyl 2-acetyl-6-[(4,6-dimethoxypyrimidin-2-yl)oxy]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
• 作为产物：
  描述：

  3-苄氧基苯乙酮 在 palladium on activated charcoal 正丁基锂 、 氢气 、 对甲苯磺酸 、 原甲酸三乙酯 作用下， 以 正己烷 、 乙酸乙酯 、 甲苯 为溶剂， 反应 3.0h， 生成 methyl 2-hydroxy-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

文献信息

• Studies of the New Herbicide KIH-6127. Part I. Novel Synthesis of Methyl 6-Acetylsalicylate as a Key Synthetic Intermediate for the Preparation of 6-Acetyl Pyrimidin-2-yl Salicylates and Analogues
  作者：Masatoshi Tamaru、Yoshihiro Saito

  DOI：10.1002/(sici)1096-9063(199606)47:2<125::aid-ps394>3.0.co;2-x

  日期：1996.6
• 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.