(1-benzyl-1H-imidazol-2-yl)-phosphonous acid bis-diethylamide | 210903-90-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: (1-benzyl-1H-imidazol-2-yl)-phosphonous acid bis-diethylamide
• 英文别名: N-[(1-benzylimidazol-2-yl)-(diethylamino)phosphanyl]-N-ethylethanamine
• CAS: 210903-90-5
• 化学式: C₁₈H₂₉N₄P
• 分子量: 332.429
• InChiKey: UTIGQFRPQSHAKQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  23
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  24.3
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (1-benzyl-1H-imidazol-2-yl)-phosphonous acid bis-diethylamide 在 氨 、 sodium 作用下， 以 甲苯 为溶剂， 反应 0.17h， 生成 N-[diethylamino(1H-imidazol-2-yl)phosphanyl]-N-ethylethanamine
  参考文献：
  名称：

  Direct Phosphorylation ofN-Protected Imidazoles and Benzoimidazoles-A Route to 1H-Imidazol(benzoimidazol)-2-yl Phosphonic and Phosphinic Acids and Their Derivatives

  摘要：

  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.

  DOI：

  10.1080/00397919808004288
• 作为产物：
  描述：

  N-苄基咪唑 在 三氯化磷 作用下， 反应 24.0h， 生成 (1-benzyl-1H-imidazol-2-yl)-phosphonous acid bis-diethylamide
  参考文献：
  名称：

  Direct Phosphorylation ofN-Protected Imidazoles and Benzoimidazoles-A Route to 1H-Imidazol(benzoimidazol)-2-yl Phosphonic and Phosphinic Acids and Their Derivatives

  摘要：

  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.

  DOI：

  10.1080/00397919808004288

文献信息

• Novel structural analogs of glyphosate based on azoles. 1. Synthesis of 1H-imidazoles containing carboxyl and phosphoryl groups in the ring
  作者：N. V. Pavlenko、T. I. Oos、Yu. L. Yagupolskii、A. van Almsick、L. Willms

  DOI：10.1007/s10593-011-0717-0

  日期：2011.4

  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.
• 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.