diethyl {(phenylamino)[4-(trifluoromethyl)phenyl]methyl}phosphonate

• 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 {(phenylamino)[4-(trifluoromethyl)phenyl]methyl}phosphonate
• 英文别名: diethyl (phenylamino)[4-(trifluoromethyl)phenyl]methylphosphonate；N-[diethoxyphosphoryl-[4-(trifluoromethyl)phenyl]methyl]aniline
• 化学式: C₁₈H₂₁F₃NO₃P
• 分子量: 387.339
• InChiKey: WQRDGFPNVVQYEM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  26
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  47.6
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  N-(4-(trifluoromethyl)benzylidene)aniline 、 亚磷酸二乙酯 在 二氯二氧化钼 作用下， 反应 0.08h， 以98%的产率得到diethyl {(phenylamino)[4-(trifluoromethyl)phenyl]methyl}phosphonate
  参考文献：
  名称：

  MoO2Cl2 as a novel catalyst for the synthesis of α-aminophosphonates

  摘要：

  This work reports the use of MoO2Cl2 as a novel catalyst for the synthesis of alpha-aminophosphonates. The system HP(O)(OEt)(2)/MoO2Cl2 (5 mol%) was applied in the synthesis of several alpha-aminophosphonates in excellent yields under solvent-free conditions. (c) 2010 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.catcom.2010.10.005

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。
• Air-stable zirconocene bis(perfluorobutanesulfonate) as a highly efficient catalyst for synthesis of α-aminophosphonates via Kabachnik–Fields reaction under solvent-free condition
  作者：Ningbo Li、Xie Wang、Renhua Qiu、Xinhua Xu、Jinyang Chen、Xiaohong Zhang、Sihai Chen、Shuangfeng Yin

  DOI：10.1016/j.catcom.2013.10.013

  日期：2014.1

  Zirconocene bis(perfluorobutanesulfonate) [Cp2Zr(OSO2C4F9)2·2H2O] was successfully synthesized by treatment of Cp2ZrCl2 with C4F9SO3Ag, and was found to have the nature of air-stability, water tolerance, high thermal stability and strong Lewis acidity. This complex showed high catalytic efficiency for the synthesis of α-aminophosphonates via Kabachnik–Fields reaction of aldehydes/ketones, amines and

  通过用C 4 F 9 SO 3处理Cp 2 ZrCl 2成功地合成了茂锆双（全氟丁烷磺酸盐）[Cp 2 Zr（OSO 2 C 4 F 9）2 ·2H 2 O]。Ag，并且具有空气稳定性，耐水性，高热稳定性和强路易斯酸性的性质。该络合物在温和无溶剂的条件下，通过Kabachnik-Fields反应醛/酮，胺和亚磷酸二乙酯，显示出对α-氨基膦酸酯合成的高催化效率。此外，在五个周期的测试中，它可以重复使用而不会失去活动。与我们先前报道的Cp 2 Zr（OSO 2 C 8 F 17）2 ·3H 2 O·THF配合物相比，该配合物表现出更好的催化活性。
• Direct Aminophosphonylation of aldehydes catalyzed by cyclopentadienyl ruthenium(II) complexes
  作者：Ivânia R. Cabrita、Sara C.A. Sousa、Pedro R. Florindo、Ana C. Fernandes

  DOI：10.1016/j.tet.2018.02.047

  日期：2018.4

  This work reports a novel method for the direct aminophosphonylation of aldehydes catalyzed by cyclopentadienyl ruthenium(II) complexes. The system HP(O)(OEt)2/[CpRu(PPh3)2Cl] was very efficient for the aminophosphonylation of aldehydes with primary and secondary amines, producing the corresponding α-aminophosphonates in good to excellent yields. This novel method has several advantages including the

  这项工作报告了一种新的方法，用于由环戊二烯基钌（II）络合物催化的醛类的直接氨基膦酰化反应。系统HP（O）（OEt）2 / [CpRu（PPh 3）2 Cl]对于醛与伯胺和仲胺的氨基膦酰基化反应非常有效，可产生相应的α-氨基膦酸酯，收率好至极佳。该新方法具有几个优点，包括使用少量催化剂（0.5 mol％），高化学选择性，无溶剂条件以及至少12个循环使用具有优异活性的催化剂[CpRu（PPh 3）2 Cl] 。
• Fluorous bis(oxazolines) ligand: Synthesis and application in Kabachnik-Fields reaction
  作者：Hongjun Wang、Tao Deng、Chun Cai

  DOI：10.1016/j.jfluchem.2014.09.024

  日期：2014.12

  A novel fluorous bis(oxazolines) ligand was synthesized with 70% overall yield in 5 steps starting from 5-aminoisophthalic acid. The ligand was applied in the one-pot synthesis of α-aminophosphonates via copper-catalyzed Kabachnik-Fields reaction, giving the corresponding products in moderate to excellent yields under mild conditions. Furthermore, the fluorous ligand could be easily recovered and reused

  从5-氨基间苯二甲酸开始，分5步合成了新型的氟双（恶唑啉）配体，总产率为70％。通过铜催化的Kabachnik-Fields反应将配体用于一锅法合成α-氨基膦酸酯，在温和条件下以中等至极好的收率得到相应的产物。此外，氟配体可以很容易地回收并没有活动的显著损失重复使用四次。
• Lanthanide triflate-catalyzed three component synthesis of α-amino phosphonates in ionic liquids. A catalyst reactivity and reusability study
  作者：Sang-gi Lee、Jung Hwan Park、Jae Kyun Lee、Jahyo Kang

  DOI：10.1039/b104967b

  日期：——

  The catalyst reactivity and reusability for the lanthanide triflate-catalyzed three component synthesis of α-amino phosphonates have been examined in room temperature ionic liquids, [bmim][X], in which the catalytic activities were very dependent on the counter anion, X, as well as on the phosphorus nucleophile, and moreover, the catalyst immobilized in an ionic liquid was reused several times without any loss of activity.

  在室温离子液体[bmim][X]中，对镧系三氟甲磺酸盐催化下的β-氨基膦酸盐的三组分合成的催化剂反应性和可重复性进行了研究，其中催化活性非常依赖于对离子X以及磷亲核体，此外，固定在离子液体中的催化剂可重复使用多次，且活性不会降低。