(1H-imidazol-5-yl)phosphonic acid bis(diethylamide) | 1314727-71-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: (1H-imidazol-5-yl)phosphonic acid bis(diethylamide)
• CAS: 1314727-71-3
• 化学式: C₁₁H₂₃N₄OP
• 分子量: 258.304
• InChiKey: XDEJVGVNKVPEHI-UHFFFAOYSA-N

物化性质

• 熔点：
  67 °C
• 沸点：
  410.4±37.0 °C(Predicted)
• 密度：
  1.10±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.91
• 重原子数：
  17.0
• 可旋转键数：
  7.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  52.23
• 氢给体数：
  1.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  (1H-imidazol-5-yl)phosphonic acid bis(diethylamide) 在 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 13.25h， 生成 methyl 1-[2-(trimethylsilyl)ethoxymethyl]-4-[bis(diethylamino)phosphoryl]-1H-imidazole-2-carboxylate
  参考文献：
  名称：

  Novel structural analogs of glyphosate based on azoles. 1. Synthesis of 1H-imidazoles containing carboxyl and phosphoryl groups in the ring

  摘要：

  A general method has been developed for the synthesis of 1H-imidazoles containing a phosphoryl group in positions 2 or 4(5) based on lithium intermediates. The possibility of further functionalization of the ring using electrophiles has also been demonstrated.

  DOI：

  10.1007/s10593-011-0717-0
• 作为产物：
  描述：

  在 水 、 双氧水 、 potassium hydroxide 作用下， 以 乙醇 、 水 、 丙酮 为溶剂， 反应 28.0h， 生成 (1H-imidazol-5-yl)phosphonic acid bis(diethylamide)
  参考文献：
  名称：

  Novel structural analogs of glyphosate based on azoles. 1. Synthesis of 1H-imidazoles containing carboxyl and phosphoryl groups in the ring

  摘要：

  A general method has been developed for the synthesis of 1H-imidazoles containing a phosphoryl group in positions 2 or 4(5) based on lithium intermediates. The possibility of further functionalization of the ring using electrophiles has also been demonstrated.

  DOI：

  10.1007/s10593-011-0717-0

文献信息

• Novel structural analogs of glyphosate based on azoles. 2*. N-Substituted imidazoles and pyrazoles obtained by alkylation of heterocycles containing carboxyl or phosphoryl groups in the ring
  作者：N. V. Pavlenko、T. I. Oos、N. V. Kirij、Yu. L. Yagupolskii、A. van Almsick、L. Willms

  DOI：10.1007/s10593-011-0777-1

  日期：2011.7

  Alkylation of 4(5)-substituted 1H-imidazoles using the corresponding reagents gave imidazole 1,4-isomers containing phosphoryl and carboxyl groups together in the ring and in the alkyl fragment. The alkylation of pyrazoles containing a carboxyl group at positions 3(5) and 4 of the ring using diethyl phosphonomethyltriflate has been studied.

  使用相应的试剂对4（5）-取代的1H-咪唑进行烷基化反应，得到在环和烷基片段中一起含有磷酰基和羧基的咪唑1,4-异构体。已经研究了使用二乙基膦酰基甲基三氟甲磺酸酯在环的3（5）和4位上含有羧基的吡唑的烷基化。