(1H-imidazol-2-yl)-phosphonic acid bis-diethylamide

• 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-2-yl)-phosphonic acid bis-diethylamide
• 英文别名: N-[diethylamino(1H-imidazol-2-yl)phosphoryl]-N-ethylethanamine
• 化学式: C₁₁H₂₃N₄OP
• 分子量: 258.304
• InChiKey: ZUTCJMPNGBRFCH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  17
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  52.2
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (1H-imidazol-2-yl)-phosphonic acid bis-diethylamide 在 盐酸 、 水 作用下， 反应 12.0h， 以0.17 g的产率得到(1H-imidazol-2-yl)phosphonic acid
  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：

  双(二乙基氨基)氯膦 在 正丁基锂 、 水 、 双氧水 、 potassium hydroxide 作用下， 以 四氢呋喃 、 乙醇 、 正己烷 、 水 、 丙酮 为溶剂， 反应 24.5h， 生成 (1H-imidazol-2-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

• Direct Phosphorylation of<i>N</i>-Protected Imidazoles and Benzoimidazoles-A Route to 1<i>H</i>-Imidazol(benzoimidazol)-2-yl Phosphonic and Phosphinic Acids and Their Derivatives
  作者：Igor V. Komarov、Aleksandr V. Strizhak、Mikhail Yu.Kornilov、Aleksandr N. Kostyuk、Andrey A. Tolmachev

  DOI：10.1080/00397919808004288

  日期：1998.7

  Synthetic approaches to 1H-imidazol-2-yl and 1H-benzoimidazol-2-yl phosphinic and phosphonic acids and their derivatives are reported, based on phosphorylation of N-protected heterocylcles by PhPOCl2 or MePOCl2. Reaction of N-alkylbenzoimidazoles with POCl3 did not lead to C-phosphorylated products in a reasonable yield, [2,2']-bis-benzoimidazolyles being formed instead.