Phosphorsaeure-(p-tolylester)-bis-(benzylamid) | 21283-93-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: Phosphorsaeure-(p-tolylester)-bis-(benzylamid)
• 英文别名: 4-MeC6H4OP(O)(NHBn)2
• CAS: 21283-93-2
• 化学式: C₂₁H₂₃N₂O₂P
• 分子量: 366.4
• InChiKey: BFFMDEHCNQGDJW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.06
• 重原子数：
  26.0
• 可旋转键数：
  8.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  50.36
• 氢给体数：
  2.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  Phosphorsaeure-(p-tolylester)-bis-(benzylamid) 在 水 、 zinc(II) chloride 作用下， 以 四氢呋喃 为溶剂， 反应 12.0h， 以70%的产率得到[4-MeC6H4OP(O)O(OH)][BnNH3]
  参考文献：
  名称：

  New phosphoroamidate compounds: Synthesis, structural characterization and studies on ZnCl2 assisted hydrolysis of the P–N bond

  摘要：

  A variety of phosphorodiamidate compounds were synthesized from the corresponding phosphorodichloridate intermediates and phosphorus oxychloride. These were completely characterized using different spectroscopic methods and single crystal X-ray diffraction studies on one of them. Studies revealed that water in the presence of a mild Lewis acid like ZnCl2 was found to assist the hydrolysis of the P-N linkage. The proof of this concept was effectively realized through the hydrolysis of hexamethylphosphoramide. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.poly.2010.04.002
• 作为产物：
  描述：

  对甲酚 在 lithium chloride 、 三氯氧磷 作用下， 以 甲苯 为溶剂， 反应 36.0h， 生成 Phosphorsaeure-(p-tolylester)-bis-(benzylamid)
  参考文献：
  名称：

  New phosphoroamidate compounds: Synthesis, structural characterization and studies on ZnCl2 assisted hydrolysis of the P–N bond

  摘要：

  A variety of phosphorodiamidate compounds were synthesized from the corresponding phosphorodichloridate intermediates and phosphorus oxychloride. These were completely characterized using different spectroscopic methods and single crystal X-ray diffraction studies on one of them. Studies revealed that water in the presence of a mild Lewis acid like ZnCl2 was found to assist the hydrolysis of the P-N linkage. The proof of this concept was effectively realized through the hydrolysis of hexamethylphosphoramide. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.poly.2010.04.002

文献信息

• Structural effects in reactions of organophosphorus compounds. I. Reactions of phosphorus oxychloride with hindered phenols
  作者：Gennady M. Kosolapoff、Charles K. Arpke、Robert W. Lamb、Hans Reich

  DOI：10.1039/j39680000815

  日期：——

  2,6-Dialkyl-phenols exhibit little steric hindrance on reaction with phosphoryl chloride unless the alkyl substituent is bulky (i.e. t-butyl). Where bulky substituents are present reaction with phosphoryl chloride occurs only in the presence of Friedel–Crafts type catalysts after either a dealkylation or a rearrangement of the ortho-placed alkyl groups, followed by O-phosphorylation, has occurred.

  除非烷基取代基是大体积的（即叔丁基），否则2，6-二烷基苯酚与磷酰氯的反应几乎没有空间位阻。在存在大量取代基的情况下，只有在邻位烷基脱烷基或重排，然后进行O-磷酸化后，才在Friedel-Crafts型催化剂存在下与磷酰氯发生反应。