diethyl {[(4-fluorophenyl)amino](phenyl)methyl}phosphonate

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: diethyl {[(4-fluorophenyl)amino](phenyl)methyl}phosphonate
• 英文别名: N-[diethoxyphosphoryl(phenyl)methyl]-4-fluoro-aniline；N-[diethoxyphosphoryl(phenyl)methyl]-4-fluoroaniline
• 化学式: C₁₇H₂₁FNO₃P
• 分子量: 337.331
• InChiKey: UJIFTMKGZMKICP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  23
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  47.6
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  苯甲醇 在 高氯酸铵 作用下， 以 neat (no solvent) 为溶剂， 反应 5.0h， 生成 diethyl {[(4-fluorophenyl)amino](phenyl)methyl}phosphonate
  参考文献：
  名称：

  Photo-Oxidation Coupled Kabachnik–Fields and Bigenelli Reactions for Direct Conversion of Benzyl alcohols to α-Aminophosphonates and Dihydropyrimidones

  摘要：

  DOI：

  10.17344/acsi.2019.5348

文献信息

• T3P®-promoted Kabachnik–Fields reaction: an efficient synthesis of α-aminophosphonates
  作者：Mátyás Milen、Péter Ábrányi-Balogh、András Dancsó、Dávid Frigyes、László Pongó、György Keglevich

  DOI：10.1016/j.tetlet.2013.07.145

  日期：2013.10

  A simple and efficient synthesis of α-aminophosphonates has been developed via the one-pot three-component reactions of aldehydes, amines, and trialkyl phosphites. The reactions occurred rapidly at room temperature in the presence of 1 equiv of propylphosphonic anhydride (T3P®) as the condensing agent, and the α-aminophosphonate products were obtained in high yields.

  通过醛，胺和亚磷酸三烷基酯的一锅式三组分反应，已经开发出一种简单而有效的α-氨基膦酸酯合成方法。该反应在室温下在1当量的丙基膦酸酐（T3P®）作为缩合剂的情况下迅速发生，并且以高收率获得了α-氨基膦酸酯产物。
• Synthesis and crystal structure of phosphonic acid and bisphosphoramidate derivatives: QSAR studies of their anti-fungal potential on Macrophomina Phaseolina (Tassi) Goid
  作者：Khodayar Gholivand、Mohsen Abbod、Ali Asghar Ebrahimi Valmoozi、Omolbanin Barzegar、Hadis Nasrollah Tabar、Rouhollah Yaghoubi、Mahdieh Hosseini、Naser Safaie、Maryam Rahimzadeh Dashtaki、Michal Dusek、Ahmad Mani-Varnosfaderani

  DOI：10.1007/s13738-020-02133-4

  日期：2021.7

  series of phosphonic acid and bisphosphoramidate derivatives were synthesized and characterized. The bioactivities against the fungal pathogen Macrophomina phaseolina and human acetylcholinesterase AChE enzyme were studied using QSAR based on multiple linear regression. L17, with (p-Cl–C6H4–NH) (p-Cl–C6H4)C(H)P(O)(OC2H5)2 skeleton, demonstrated a great mortality on the M. phaseolina mycelial growth by

  合成并表征了一系列膦酸和双磷酸氨基酯衍生物。基于多重线性回归的QSAR研究了针对真菌病原体菜豆巨噬菌和人乙酰胆碱酯酶AChE酶的生物活性。具有（p -Cl–C 6 H 4 -NH）（p -Cl–C 6 H 4）C（H）P（O）（OC 2 H 5）2骨架的L17在M上显示出很高的死亡率。菜豆在150 mg / L时，菌丝体生长受到83％的抑制；另一种测试的衍生物对真菌表现出中等至弱的抗真菌活性。基于GA-MLR方法的QSAR模型揭示了3D描述符（De，Mor18e，H8m和Mor30p）对抗真菌活性的重要性。它显示出良好的预测所研究分子杀真菌活性的能力。具有（m -CH 3 -NC 5 H 4 -NH）（m -CH 3 -C 6 H 4）C（H）P（O）（OCH 3）2骨架的另一种衍生物L5显示出最有效的抗- AChE活动。电子参数ΔE L-H和E LUMO，对人类AChE的贡献最大。作者认
• Catalyst and solvent-free, ultrasound promoted rapid protocol for the one-pot synthesis of α-aminophosphonates at room temperature
  作者：Bashir Dar、Amrinder Singh、Akshya Sahu、Praveen Patidar、Arup Chakraborty、Meena Sharma、Baldev Singh

  DOI：10.1016/j.tetlet.2012.07.123

  日期：2012.10

  An ultrasound promoted easy, efficient, and environment friendly process has been devised for the synthesis of α-aminophosphonates within seconds through a one-pot three-component condensation of the aldehydes, amines, and triethylphosphite. The desired products were obtained in excellent yields and in high purity under solvent-free and catalyst-free conditions. Study with various aldehydes and amines

  已经设计了超声促进的简单，有效和环境友好的方法，用于通过醛，胺和亚磷酸三乙酯的一锅式三组分缩合在几秒钟内合成α-氨基膦酸酯。在无溶剂和无催化剂的条件下，可以以极高的收率和高纯度获得所需的产物。对各种醛和胺的研究表明，超声辐射在α-氨基膦酸酯的直接合成中起着关键作用。
• Aluminium nitride catalyzed solvent-free synthesis of some novel biologically active α-aminophosphonates
  作者：S. U. Tekale、S. S. Kauthale、R. U. Shaikh、R. P. Marathe、R. B. Nawale、R. P. Pawar

  DOI：10.1007/s13738-013-0344-z

  日期：2014.6

  A green and atom-efficient one-pot protocol for the synthesis of some novel α-aminophosphonates using micron-particulate AlN/Al as a new reusable heterogeneous catalyst by the Kabachnik–Fields reaction under solvent-free conditions has been developed. The synthesized α-aminophosphonates were screened for several biological activities. They all were investigated to exhibit moderate to promising antioxidant

  通过无溶剂条件下的Kabachnik-Fields反应，开发了一种绿色高效且原子效率高的一锅法，用于使用微米颗粒AlN / Al作为新型可重复使用的多相催化剂，合成某些新型α-氨基膦酸酯。筛选合成的α-氨基膦酸酯的几种生物活性。他们都被证明具有中等至有希望的抗氧化剂，抗炎和细胞毒性特性。
• A Green Approach to the Synthesis of α-Amino Phosphonate in Water Medium: Carbene Insertion into the N–H Bond by Cu(I) Catalyst
  作者：Kankanala Ramakrishna、Jisha Mary Thomas、Chinnappan Sivasankar

  DOI：10.1021/acs.joc.6b01940

  日期：2016.10.21

  achieved via phosphonate substituted carbene insertion into the N–H bond of aniline catalyzed by readily available copper salt under mild reaction conditions in water. In order to find an efficient catalyst for carbene insertion reaction in neat water, a large number of transition metal catalysts were screened, and we found that the [Cu(CH3CN)4]ClO4 was the best catalyst under employed reaction conditions

  由于氨基膦酸酯在生物系统中的重要应用，其合成更为重要。文献中几乎没有已知的方法可以制造这些分子。但是，已知方法有其自身的缺点。在这方面，通过在水中的温和反应条件下容易获得的铜盐催化的膦酸酯取代的卡宾插入苯胺的NH键中，可以实现不同种类的氨基膦酸酯的合成。为了找到在纯净水中卡宾插入反应的有效催化剂，筛选了大量的过渡金属催化剂，我们发现[Cu（CH 3 CN）4 ] ClO 4在采用的反应条件下是最佳的催化剂。使用这种环境友好的方法（铜在水中的催化反应），已经合成，分离了许多具有生物学重要性的氨基膦酸酯（37个实例），并使用标准的分析和光谱技术进行了表征。