diethyl [1-(4-methoxyphenylamino)-butyl]-phosphonate | 934842-64-5

• 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: diethyl [1-(4-methoxyphenylamino)-butyl]-phosphonate
• 英文别名: diethyl (n-propyl)-N-(phenyl)aminomethylphosphonate；N-(1-diethoxyphosphorylbutyl)-4-methoxyaniline
• CAS: 934842-64-5
• 化学式: C₁₅H₂₆NO₄P
• 分子量: 315.35
• InChiKey: UPXIIXXYRXETNQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  21
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  56.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  diethyl [1-(4-methoxyphenylamino)-butyl]-phosphonate 在 ammonium cerium(IV) nitrate 作用下， 以 水 、 乙腈 为溶剂， 反应 1.0h， 以65%的产率得到diethyl (1-amino-butyl)-phosphonate
  参考文献：
  名称：

  Synthesis of α-Phosphorylated α,β-Unsaturated Imines and Their Selective Reduction to Vinylogous and Saturated α-Aminophosphonates

  摘要：

  [GRAPHIC]An efficient synthesis of alpha,beta-unsaturated imines derived from alpha-aminophosphonates is achieved through aza-Wittig reaction of P-trimethyl phosphazenes with beta,gamma-unsaturated alpha-ketophosphonates. Selective 1,2-reduction of such 1-azadienes affords beta,gamma-unsaturated alpha-aminophosphonates, phosphorylated analogs of vinylglycines, which are hydrogenated to yield saturated alpha-aminophosphonate derivatives.

  DOI：

  10.1021/jo062609+
• 作为产物：
  描述：

  1-叠氮基-4-甲氧基苯 在 palladium on activated charcoal 氢气 、 三甲基膦 作用下， 以 乙醇 、 甲苯 为溶剂， -78.0~25.0 ℃ 、551.58 kPa 条件下， 反应 52.0h， 生成 diethyl [1-(4-methoxyphenylamino)-butyl]-phosphonate
  参考文献：
  名称：

  Synthesis of α-Phosphorylated α,β-Unsaturated Imines and Their Selective Reduction to Vinylogous and Saturated α-Aminophosphonates

  摘要：

  [GRAPHIC]An efficient synthesis of alpha,beta-unsaturated imines derived from alpha-aminophosphonates is achieved through aza-Wittig reaction of P-trimethyl phosphazenes with beta,gamma-unsaturated alpha-ketophosphonates. Selective 1,2-reduction of such 1-azadienes affords beta,gamma-unsaturated alpha-aminophosphonates, phosphorylated analogs of vinylglycines, which are hydrogenated to yield saturated alpha-aminophosphonate derivatives.

  DOI：

  10.1021/jo062609+

文献信息

• A green one-pot three-component synthesis of α-aminophosphonates under solvent-free conditions and ultrasonic irradiation using Fe₃O₄@SiO₂-imid-PMAⁿ as magnetic catalyst
  作者：Mohsen Esmaeilpour、Saeed Zahmatkesh、Jaber Javidi、Elahe Rezaei

  DOI：10.1080/10426507.2016.1269232

  日期：2017.5.4

  GRAPHICAL ABSTRACT ABSTRACT An efficient and environment friendly process for the synthesis of α-aminophosphonates has been devised. Through a one-pot three-component condensation of various aldehydes, amines, and triethyl phosphite in the presence of Fe3O4@SiO2-imid-PMAn nanoparticles as magnetic catalysts under solvent-free conditions and ultrasonic irradiation, α-aminophosphonates were obtained

  图形摘要 摘要 已设计出一种高效且环境友好的合成 α-氨基膦酸酯的方法。在Fe3O4@SiO2-imid-PMAn纳米粒子作为磁性催化剂存在下，在无溶剂条件和超声波照射下，通过各种醛、胺和亚磷酸三乙酯的一锅三组分缩合反应，以优异的收率获得了α-氨基膦酸酯. 将室温下无溶剂条件下的反应与超声辅助反应进行了比较。这种新方法具有显着的优点，例如反应时间短、收率高、易于纯化以及无需任何繁琐的后处理或纯化。上述催化剂可以很容易地通过外部磁场回收，并且可以重复使用六个连续的反应循环而不会显着损失活性。此外，还研究了反应循环后催化剂的 SEM 和 DLS。
• α-Ketiminophosphonates: Synthesis and Applications
  作者：Javier Vicario、Domitila Aparicio、Francisco Palacios

  DOI：10.1080/10426507.2010.521211

  日期：2011.3.31
• Synthesis of α-Phosphorylated α,β-Unsaturated Imines and Their Selective Reduction to Vinylogous and Saturated α-Aminophosphonates
  作者：Francisco Palacios、Javier Vicario、Agnieszka Maliszewska、Domitila Aparicio

  DOI：10.1021/jo062609+

  日期：2007.3.1

  [GRAPHIC]An efficient synthesis of alpha,beta-unsaturated imines derived from alpha-aminophosphonates is achieved through aza-Wittig reaction of P-trimethyl phosphazenes with beta,gamma-unsaturated alpha-ketophosphonates. Selective 1,2-reduction of such 1-azadienes affords beta,gamma-unsaturated alpha-aminophosphonates, phosphorylated analogs of vinylglycines, which are hydrogenated to yield saturated alpha-aminophosphonate derivatives.