diethyl [2-(4-t-butylphenoxymethyl)-9-methylsulfanyl-7H-pyrazolo[4,3-e]-1,2,4-triazolo[1,5-d]pyrimidin-7-yl](4-fluorophenyl)methylphosphonate | 1147868-74-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 三唑并嘧啶类
• 英文名称: diethyl [2-(4-t-butylphenoxymethyl)-9-methylsulfanyl-7H-pyrazolo[4,3-e]-1,2,4-triazolo[1,5-d]pyrimidin-7-yl](4-fluorophenyl)methylphosphonate
• 英文别名: 4-[(4-Tert-butylphenoxy)methyl]-10-[diethoxyphosphoryl-(4-fluorophenyl)methyl]-12-methylsulfanyl-3,5,6,8,10,11-hexazatricyclo[7.3.0.02,6]dodeca-1(9),2,4,7,11-pentaene
• CAS: 1147868-74-3
• 化学式: C₂₉H₃₄FN₆O₄PS
• 分子量: 612.665
• InChiKey: QJWZNVMIBDPPTM-UHFFFAOYSA-N

物化性质

• 熔点：
  104.1-105.6 °C
• 密度：
  1.35±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 重原子数：
  42
• 可旋转键数：
  12
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  131
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为产物：
  描述：

  diethyl [(4-cyano-5-ethoxymethyleneamino-3-methylsulfanylpyrazol-1-yl)(4-fluorophenyl)methyl]phosphonate 、 (4-叔丁基苯氧基)-乙酸肼 以 甲乙醚 为溶剂， 以70%的产率得到diethyl [2-(4-t-butylphenoxymethyl)-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

文献信息

• A Convenient Synthesis and Herbicidal Activity of<i>N</i>-phosphonoalkylpyrazolo[4,3-<i>e</i>][1,2,4]-triazolo[1,5-<i>d</i>]pyrimidines
  作者：Lin-Xia Xiao、Ke Li、De-Qing Shi

  DOI：10.1080/10426500802070270

  日期：2008.11.7

  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.