diethyl(N-(4-nitrophenyl))phosphoramide | 63542-12-1

• 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(N-(4-nitrophenyl))phosphoramide
• 英文别名: diethyl (4-nitrophenyl)phosphoramidate；Diethyl 4-nitrophenylphosphoramidat；phosphoramidic acid, N-(4-nitrophenyl)-, diethyl ester；N-diethoxyphosphoryl-4-nitroaniline
• CAS: 63542-12-1
• 化学式: C₁₀H₁₅N₂O₅P
• 分子量: 274.213
• InChiKey: RBHGFLZXNUNDOA-UHFFFAOYSA-N

物化性质

• 熔点：
  139-140 °C(Solv: methanol (67-56-1))
• 沸点：
  367.0±44.0 °C(Predicted)
• 密度：
  1.323±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  18
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  93.4
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  diethyl(N-(4-nitrophenyl))phosphoramide 在 盐酸 、 铁粉 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 0.5h， 以92%的产率得到Diethyl (4-aminophenyl)phosphoramidate
  参考文献：
  名称：

  Potential antitumor agents. 37. Organophosphorus derivatives of 9-anilinoacridine

  摘要：

  A series of 9-anilinoacridine derivatives substituted in the anilino ring with a variety of phosphoramide and related substitutents has been prepared, and the antitumor activity has been evaluated both in vivo and in vitro against the L1210 or P-388 mouse leukemia systems. The DNA-binding properties were measured using the ethidium displacement method, and the structural requirements for strong binding were found to differ from those for antileukemic activity. For high biological activity a marked preference for oxygen-containing substituents on the phosphorus atom was noted, while for high DNA binding a requirement for nitrogen-containing or cyclized substituents was observed. The most active congeners, as assayed in both in vitro and in vivo systems, were comparable in activity to the clinically utilized anilinoacridine derivative N-[4'-(9-acridinylamino)-3'-methoxyphenyl]methanesulfonamide (m-AMSA, amsacrine).

  DOI：

  10.1021/jm00352a027
• 作为产物：
  描述：

  N-(4-nitrophenyl)phosphoramidic dichloride 、 sodium ethanolate 以 乙醇 为溶剂， 以77%的产率得到diethyl(N-(4-nitrophenyl))phosphoramide
  参考文献：
  名称：

  Potential antitumor agents. 37. Organophosphorus derivatives of 9-anilinoacridine

  摘要：

  A series of 9-anilinoacridine derivatives substituted in the anilino ring with a variety of phosphoramide and related substitutents has been prepared, and the antitumor activity has been evaluated both in vivo and in vitro against the L1210 or P-388 mouse leukemia systems. The DNA-binding properties were measured using the ethidium displacement method, and the structural requirements for strong binding were found to differ from those for antileukemic activity. For high biological activity a marked preference for oxygen-containing substituents on the phosphorus atom was noted, while for high DNA binding a requirement for nitrogen-containing or cyclized substituents was observed. The most active congeners, as assayed in both in vitro and in vivo systems, were comparable in activity to the clinically utilized anilinoacridine derivative N-[4'-(9-acridinylamino)-3'-methoxyphenyl]methanesulfonamide (m-AMSA, amsacrine).

  DOI：

  10.1021/jm00352a027

文献信息

• A Visible-Light-Promoted Metal-Free Strategy towards Arylphosphonates: Organic-Dye-Catalyzed Phosphorylation of Arylhydrazines with Trialkylphosphites
  作者：Rui Li、Xiaolan Chen、Shengkai Wei、Kai Sun、Lulu Fan、Yan Liu、Lingbo Qu、Yufen Zhao、Bing Yu

  DOI：10.1002/adsc.201801122

  日期：2018.12.21

  A visible‐light‐induced metal‐free catalytic system was developed for the synthesis of arylphosphonates starting from arylhydrazines and trialkylphosphites. By using the inexpensive eosin B as catalyst, sub‐stoichiometric amounts of DABCO, and ambient air as oxidant, diverse arylphosphonates were obtained under visible‐light irradiation. Notably, this catalytic system is suitable for gram‐scale reaction

  开发了可见光诱导的无金属催化体系，用于从芳基肼和亚磷酸三烷基酯开始合成芳基膦酸酯。通过使用廉价的曙红B作为催化剂，亚化学计量的DABCO和周围空气作为氧化剂，在可见光照射下获得了多种芳基膦酸酯。值得注意的是，该催化系统通过利用日光作为照明源，适用于克级反应。
• The Phosporylation of Aniline Derivatives in Biphase Systems
  作者：Gheorghe Ilia、Mihaela Petric、Lavinia Macarie、Smaranda Iliescu、Adriana Popa

  DOI：10.1080/10426500500536614

  日期：2006.6.1

  Aniline derivatives were phosphorylated in biphase systems using three methods. A comparative study was performed. The best results were obtained when a solid-liquid system was used. This method is the easiest and lead to higher yields (54-81%).
• Fe3O4@MgO nanoparticles as an efficient recyclable catalyst for the synthesis of phosphoroamidates via the Atherton–Todd reaction
  作者：Babak Kaboudin、Foad Kazemi、Fereshteh Habibi

  DOI：10.1016/j.tetlet.2015.09.129

  日期：2015.11

  A simple and efficient method is presented for the synthesis of phosphoroamidates in moderate to good yield via the Atherton-Todd coupling of primary amines with H-dialkyl phosphites using Fe3O4@MgO nanoparticles as a recyclable catalyst. (C) 2015 Elsevier Ltd. All rights reserved.
• Directing effects of phosphorus-containing groups in aromatic substitution. Orientation in nitration of some N-arylphosphoramidates and phosphorothioamidates in protic and aprotic media
  作者：Gerald W. Buchanan、Steffen H. Preusser

  DOI：10.1021/jo00146a043

  日期：1982.12
• REWCASTLE, G. W.;BAGULEY, B. C.;CAIN, B. F., J. MED. CHEM., 1982, 25, N 10, 1231-1235
  作者：REWCASTLE, G. W.、BAGULEY, B. C.、CAIN, B. F.

  DOI：——

  日期：——