2-[3-(benzyloxy)phenyl]-2-methyl-1,3-dioxolane | 143613-10-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 2-[3-(benzyloxy)phenyl]-2-methyl-1,3-dioxolane
• 英文别名: 3-Benzyloxyacetophenone ethylene ketal；2-Methyl-2-(3-phenylmethoxyphenyl)-1,3-dioxolane
• CAS: 143613-10-9
• 化学式: C₁₇H₁₈O₃
• 分子量: 270.328
• InChiKey: FGUDCTNVQZDRGQ-UHFFFAOYSA-N

物化性质

• 沸点：
  403.3±45.0 °C(predicted)
• 密度：
  1.135±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  27.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-[3-(benzyloxy)phenyl]-2-methyl-1,3-dioxolane 在 palladium on activated charcoal 正丁基锂 、 盐酸肼 、 氢气 、 sodium hydride 、 potassium carbonate 作用下， 以 甲醇 、 正己烷 、 乙酸乙酯 、 N,N-二甲基甲酰胺 、 丙酮 、 甲苯 为溶剂， 反应 37.5h， 生成 Ethyl 2-[8-(4,6-dimethoxypyrimidin-2-yl)oxy-4-methyl-1-oxophthalazin-2-yl]acetate
  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 potassium carbonate 、 对甲苯磺酸 、 原甲酸三乙酯 作用下， 以 乙腈 为溶剂， 反应 3.0h， 生成 2-[3-(benzyloxy)phenyl]-2-methyl-1,3-dioxolane
  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 III. Synthesis and Structure-Activity Studies of Analogues of KIH-6127 against Barnyard Grass (<i>Echinochloa oryzicola</i>)*
  作者：Masatoshi Tamaru、Naoshi Masuyama、Masahiro Sato、Fumiaki Takabe、Jun Inoue、Ryo Hanai

  DOI：10.1002/(sici)1096-9063(199701)49:1<76::aid-ps491>3.0.co;2-e

  日期：1997.1
• 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