diethyl [(4-cyano-5-ethoxymethyleneamino-3-methylsulfanylpyrazol-1-yl)(4-fluorophenyl)methyl]phosphonate | 1147868-54-9

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: diethyl [(4-cyano-5-ethoxymethyleneamino-3-methylsulfanylpyrazol-1-yl)(4-fluorophenyl)methyl]phosphonate
• CAS: 1147868-54-9
• 化学式: C₁₉H₂₄FN₄O₄PS
• 分子量: 454.462
• InChiKey: UIUOVKVRZIJIII-UHFFFAOYSA-N

物化性质

• 熔点：
  77-78 °C
• 沸点：
  622.8±55.0 °C(predicted)
• 密度：
  1.30±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.13
• 重原子数：
  30.0
• 可旋转键数：
  11.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  98.73
• 氢给体数：
  0.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  3-chlorophenoxyacetic acid hydrazide 、 diethyl [(4-cyano-5-ethoxymethyleneamino-3-methylsulfanylpyrazol-1-yl)(4-fluorophenyl)methyl]phosphonate 以 甲乙醚 为溶剂， 以76%的产率得到diethyl [2-(3-chlorophenoxymethyl)-9-methylsulfanyl-7H-pyrazolo[4,3-e]-1,2,4-triazolo[1,5-d]pyrimidin-7-yl](4-fluorophenyl)methylphosphonate
  参考文献：
  名称：

  A Convenient Synthesis and Herbicidal Activity ofN-phosphonoalkylpyrazolo[4,3-e][1,2,4]-triazolo[1,5-d]pyrimidines

  摘要：

  An important building block, diethyl [(5-amino-4-cyano-3-methylsulfanyl-pyrazol-1-yl)-(4-fluorophenyl)methyl] phosphonate (3) was efficiently synthesized via the condensation of 1-hydrazino-1-(4-fluorophenyl)methyl phosphonate (1) with 2-[bis(methylthio)methylene]malononitrile (2).3 reacted with triethyl orthoformate to afford diethyl [(4-cyano-5-ethoxymethyleneamino-3-methylsulfanyl-pyrazol-1-yl)-(4-fluorophenyl)methyl] phosphonate (4), which reacted with various acyl hydrazines in refluxing 2-methoxyethanol to provide the target compounds (5) in good yields directly. The results of preliminary bioassay indicated that compounds 5 possess potent herbicidal activity against the roots of monocotyledonous (barnyard grass) and dicotyledonous (oil rape) plants, and could be further developed as potential herbicides.

  DOI：

  10.1080/10426500802070270
• 作为产物：
  描述：

  diethyl [(5-amino-4-cyano-3-methylsulfanylpyrazol-1-yl)(4-fluorophenyl)methyl]phosphonate 、 原甲酸三乙酯 反应 2.0h， 以89%的产率得到diethyl [(4-cyano-5-ethoxymethyleneamino-3-methylsulfanylpyrazol-1-yl)(4-fluorophenyl)methyl]phosphonate
  参考文献：
  名称：

  A Convenient Synthesis and Herbicidal Activity ofN-phosphonoalkylpyrazolo[4,3-e][1,2,4]-triazolo[1,5-d]pyrimidines

  摘要：

  An important building block, diethyl [(5-amino-4-cyano-3-methylsulfanyl-pyrazol-1-yl)-(4-fluorophenyl)methyl] phosphonate (3) was efficiently synthesized via the condensation of 1-hydrazino-1-(4-fluorophenyl)methyl phosphonate (1) with 2-[bis(methylthio)methylene]malononitrile (2).3 reacted with triethyl orthoformate to afford diethyl [(4-cyano-5-ethoxymethyleneamino-3-methylsulfanyl-pyrazol-1-yl)-(4-fluorophenyl)methyl] phosphonate (4), which reacted with various acyl hydrazines in refluxing 2-methoxyethanol to provide the target compounds (5) in good yields directly. The results of preliminary bioassay indicated that compounds 5 possess potent herbicidal activity against the roots of monocotyledonous (barnyard grass) and dicotyledonous (oil rape) plants, and could be further developed as potential herbicides.

  DOI：

  10.1080/10426500802070270