methyl 2-(benzyloxy)-6-(2-methyl-1,3-dioxolan-2-yl)benzoate | 143613-14-3

• 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-(benzyloxy)-6-(2-methyl-1,3-dioxolan-2-yl)benzoate
• 英文别名: Methyl 2-(2-methyl-1,3-dioxolan-2-yl)-6-phenylmethoxybenzoate
• CAS: 143613-14-3
• 化学式: C₁₉H₂₀O₅
• 分子量: 328.365
• InChiKey: FRDAKYCAKAROOB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  24
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  54
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  methyl 2-(benzyloxy)-6-(2-methyl-1,3-dioxolan-2-yl)benzoate 在 palladium on activated charcoal 盐酸肼 、 氢气 、 sodium hydride 、 potassium carbonate 作用下， 以 甲醇 、 乙酸乙酯 、 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 反应 34.5h， 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-苄氧基苯乙酮 在 正丁基锂 、 对甲苯磺酸 、 原甲酸三乙酯 作用下， 以 正己烷 、 甲苯 为溶剂， 反应 6.5h， 生成 methyl 2-(benzyloxy)-6-(2-methyl-1,3-dioxolan-2-yl)benzoate
  参考文献：
  名称：

  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

  摘要：

  DOI：

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

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
• A Practical Synthesis of 6-Acetylsalicylic Acid Methyl Ester
  作者：Masatoshi Tamaru、Kazuto Umezu、Chika Maejima、Hiroyuki Kageyama、Yoshikazu Kimura

  DOI：10.1080/00397919408010591

  日期：1994.10

  A new and efficient synthesis of the tide compound is reported. The method includes a regioselective ortho-lithiation step in none polar solvents at an ambient temperature and the overall yield for 5 steps is more than 70% from a commercially available 3-hydroxyacetophenone.
• 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.