diethyl α-phenyl-α-(propylamino)methylphosphonate | 93865-80-6

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机膦酸及其衍生物
• 英文名称: diethyl α-phenyl-α-(propylamino)methylphosphonate
• 英文别名: diethyl ((phenyl)n-propylaminomethyl)phosphonate；(EtO)2P(O)CH(Ph)NHPr；α-Propylamino-benzylphosphonsaeurediaethylester；N-[diethoxyphosphoryl(phenyl)methyl]propan-1-amine
• CAS: 93865-80-6
• 化学式: C₁₄H₂₄NO₃P
• 分子量: 285.323
• InChiKey: JEAIELFDXIKWCJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  19
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  47.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  diethyl α-phenyl-α-(propylamino)methylphosphonate 、 2-溴甲基丙烯酸乙酯 在 三乙胺 作用下， 以 乙腈 为溶剂， 以70 %的产率得到ethyl 2-((((diethoxyphosphoryl)(phenyl)methyl)(propyl)amino)methyl)acrylate
  参考文献：
  名称：

  通过 1,3-偶极环加成反应轻松区域选择性合成新型功能化异恶唑啉衍生物

  摘要：

  摘要 报道了各种含氨基膦酸酯的异恶唑啉衍生物的有效和原始合成。在温和条件下，用作亲偶极试剂的β-乙氧基羰基N-甲基膦酸化烯丙基胺与氯肟发生 1,3-偶极环加成反应，很容易合成各种取代化合物库。

  DOI：

  10.1080/00397911.2022.2144379
• 作为产物：
  描述：

  N-丙基苄亚基胺 、 亚磷酸二乙酯 生成 diethyl α-phenyl-α-(propylamino)methylphosphonate
  参考文献：
  名称：

  Another Example of the Novel Conversion of a Phosphonate to a Phosphate

  摘要：

  DOI：

  10.1021/jo01047a055

文献信息

• Synthesis of α-aminophosphonates using carbon nanotube supported imidazolium salt-based ionic liquid as a novel and environmentally benign catalyst
  作者：Kaveh Parvanak Boroujeni、Elham Rezazadeh Shirazi、Mohammad Mahdi Doroodmand

  DOI：10.1080/10426507.2015.1072182

  日期：2016.5.3

  Abstract A supported acidic catalyst was easily prepared via anchoring imidazolium salt-based ionic liquid onto multiwalled carbon nanotube by covalent bonds. This novel immobilized acidic ionic liquid effectively catalyzed the one-pot synthesis of α-aminophosphonates from the reaction of amines and aldehydes with diethyl phosphite. The catalyst can be easily recovered and reused without appreciable

  摘要 通过将咪唑鎓盐基离子液体通过共价键锚定在多壁碳纳米管上，很容易制备负载型酸性催化剂。这种新型固定化酸性离子液体有效地催化了胺和醛与亚磷酸二乙酯反应一锅法合成 α-氨基膦酸酯。催化剂可以很容易地回收和再利用，而不会明显改变其效率。图形概要
• Synthesis of α-aminophosphonates from α-hydroxyphosphonates; a theoretical study
  作者：Nóra Zsuzsa Kiss、Zita Rádai、Zoltán Mucsi、György Keglevich

  DOI：10.1002/hc.21324

  日期：2016.9

  the substitution of the α-hydroxyphosphonates so-formed by primary amines to afford α-aminophosphonates, were evaluated by quantum chemical calculations at the B3LYP/6-31G(d,p) level. An unexpected neighboring group effect was found to enhance the substitution. A series of new α-aminophosphonates was synthesized by the microwave-assisted substitution of α-hydroxyphosphonates by alkylamines.

  两种类型的反应，即苯甲醛和苯乙酮与亚磷酸二乙酯的 Pudovik 反应，以及由伯胺形成的 α-羟基膦酸酯取代生成 α-氨基膦酸酯，在 B3LYP/6- 31G(d,p) 水平。发现意想不到的相邻组效应增强了取代。通过烷基胺对α-羟基膦酸酯的微波辅助取代，合成了一系列新的α-氨基膦酸酯。
• A study on the Kabachnik-Fields reaction of benzaldehyde, propylamine, and diethyl phosphite by in situ Fourier transform IR spectroscopy
  作者：György Keglevich、András Fehérvári、István Csontos

  DOI：10.1002/hc.20676

  日期：2011.9

  The phospha-Mannich condensation of benzaldehyde, n-propylamine, and diethyl phosphite carried out at 80°C in acetonitrile takes place via the imine (PhCNPr) intermediate as suggested by in situ FT-IR spectroscopy. © 2011 Wiley Periodicals, Inc. Heteroatom Chem 22:599–604, 2011; View this article online at wileyonlinelibrary.com. DOI 10.1002/hc.20676

  如原位 FT-IR 光谱所示，苯甲醛、正丙胺和亚磷酸二乙酯在 80°C 下在乙腈中通过亚胺 (PhCNPr) 中间体进行磷-曼尼希缩合反应。© 2011 Wiley Periodicals, Inc. 杂原子化学 22:599–604, 2011; 在 wileyonlinelibrary.com 上在线查看这篇文章。DOI 10.1002/hc.20676
• One-Pot Synthesis of α-Amino Phosphonates from Aldehydes Using Lanthanide Triflate as a Catalyst
  作者：Changtao Qian、Taisheng Huang

  DOI：10.1021/jo971242t

  日期：1998.6.1
• A neighbouring group effect leading to enhanced nucleophilic substitution of amines at the hindered α-carbon atom of an α-hydroxyphosphonate
  作者：Nóra Zsuzsa Kiss、Anna Kaszás、László Drahos、Zoltán Mucsi、György Keglevich

  DOI：10.1016/j.tetlet.2011.11.026

  日期：2012.1

  Diethyl alpha-hydroxy-benzylphosphonate undergoes nucleophilic substitution with primary amines of sufficient reactivity at around 100 degrees C to afford the corresponding alpha-aminophosphonates. The substitution can be enhanced by microwave irradiation. The reaction takes place with surprising ease due to the neighbouring group effect of the P=O moiety as was justified by DFT calculations carried out to evaluate the mechanism of the substitution under discussion. (C) 2011 Elsevier Ltd. All rights reserved.