N-[1-[dimethoxy(oxido)phosphaniumyl]butyl]aniline | 1017241-66-5

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: N-[1-[dimethoxy(oxido)phosphaniumyl]butyl]aniline
• CAS: 1017241-66-5
• 化学式: C₁₂H₂₀NO₃P
• 分子量: 257.269
• InChiKey: ZYRFKPQEIOJNEU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  17
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  53.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  正丁醛 、 亚磷酸二甲酯 、 苯胺 在 ZnO nanoparticles ca. 22nm 作用下， 反应 18.0h， 以78%的产率得到N-[1-[dimethoxy(oxido)phosphaniumyl]butyl]aniline
  参考文献：
  名称：

  ZnO Nanoparticles as an Efficient Catalyst for the One-Pot Synthesis of α-Amino Phosphonates

  摘要：

  氧化锌纳米颗粒（ZnO NPs，约22纳米）被用作有效催化剂，在无溶剂的条件下，室温下对醛、芳香胺和双烷基磷酸酯进行三组分耦合反应，以生成各种α-氨基膦酸酯。与已知方法相比，通过简单的实验程序获得了满意的结果，产率高。该催化剂经过回收和重复使用五次后，其催化活性仅略有下降。

  DOI：

  10.1055/s-0028-1088135

文献信息

• Organocatalytic Synthesis of α-Aminophosphonates Using o-Benzenedisul fonimide as a Recyclable Bronsted Acid Catalyst
  作者：Nasrin Farahani、Jafar Akbari

  DOI：10.2174/1570178614666170321123731

  日期：2017.7.19

  Background: One-Pot three component preparation of α-aminophosphonates in the presence of o-benzenedisulfonimide as efficient acidic organocatalyst has been described. The catalyst can be recovered for further reactions and reused without any loss of efficiency. Methods: A very simple protocol was followed in the reaction process. Initially, we attempted a three component coupling of benzaldehyde with aniline and trimethylphosphite using o-benzenedisulfonimide (5 mol%). The reaction proceeded smoothly at r.t under solvent free conditions and the desired product. Results: The reactions worked well with almost all the aldehydes, heteroaryl aldehydes and ketones; at the end of the reaction, the product could be separated by usual work up. Finally, the water tolerant catalyst may be recycled from water, because of its good solubility in water. Conclusion: The catalyst is a safe, nonvolatile, and noncorrosive Brønsted acid; it is readily recovered at the end of the reactions simply by evaporating the aqueous washings. The products are generally obtained in good yields and short time under simple and mild reaction conditions.

  背景：描述了一种在o-苯二磺酰亚胺作为高效酸性有机催化剂的存在下，一锅三组分制备α-氨基膦酸酯的方法。该催化剂可以回收以进行进一步反应，并且没有效率损失。 方法：在反应过程中采用了一种非常简单的协议。最初，我们尝试将苯甲醛与苯胺和三甲基膦酸酯进行三组分偶联，催化剂为o-苯二磺酰亚胺（5 mol%）。反应在室温下无溶剂条件下顺利进行，得到了所需的产物。 结果：该反应在几乎所有醛类、杂环醛和酮类中效果良好；反应结束时，产物可以通过常规的后处理分离。最后，该耐水催化剂由于其良好的水溶性，可以从水中回收再利用。 结论：该催化剂是一种安全、非挥发性和非腐蚀性的Brønsted酸；在反应结束时可以通过简单蒸发水洗液轻松回收。一般在简单温和的反应条件下，产物可以以良好的产率和短的时间获得。
• Trifluoroethanol as a metal-free, homogeneous and recyclable medium for the efficient one-pot synthesis of α-amino nitriles and α-amino phosphonates
  作者：Akbar Heydari、Samad Khaksar、Mahmood Tajbakhsh

  DOI：10.1016/j.tetlet.2008.10.106

  日期：2009.1

  Trifluoroethanol is found to be an efficient and recyclable medium in promoting one-pot, three-component coupling reactions of aldehydes or ketones, amines and trimethylsilyl cyanide or trimethyl phosphite to afford the corresponding α-amino nitriles or α-amino phosphonates in high yields. This protocol does not require the use of an acid or base catalyst.

  发现三氟乙醇是促进醛或酮，胺和三甲基甲硅烷基氰化物或亚磷酸三甲酯的一锅，三组分偶联反应的有效且可循环的介质，以高收率提供相应的α-氨基腈或α-氨基膦酸酯。该方案不需要使用酸或碱催化剂。
• Pentafluorophenylammonium triflate (PFPAT): A new organocatalyst for the one-pot three-component synthesis of α-aminophosphonates
  作者：FATEMEH MALAMIRI、SAMAD KHAKSAR

  DOI：10.1007/s12039-014-0636-6

  日期：2014.5

  from aldehydes and amines) to yield the corresponding coupling products in good yield. The organocatalyst is air-stable, cost-effective, easy to handle, and easily removed from the reaction mixtures. α-Aminophosphonate derivatives were synthesized in excellent yield using PFPAT as an efficient organocatalyst.

  在催化量的三氟甲磺酸五氟苯基铵（10摩尔％）的存在下，亚磷酸二甲酯与亚胺（由醛和胺原位生成）反应，以高收率得到相应的偶联产物。有机催化剂是空气稳定的，成本有效的，易于处理的，并且易于从反应混合物中除去。 使用PFPAT作为有效的有机催化剂，可以出色的产率合成α-氨基膦酸酯衍生物。
• Al(H₂PO₄)₃as an Efficient and Reusable Catalyst for One-pot Three-component Synthesis of<i>α</i>-Amino Phosphonates under Solvent-free Conditions
  作者：Malek Taher Maghsoodlou、Sayyed Mostafa Habibi-Khorassani、Reza Heydari、Nourollah Hazeri、Seyed Sajad Sajadikhah、Mohsen Rostamizadeh

  DOI：10.1002/cjoc.201090067

  日期：2010.2

  Synthesis of α‐amino phosphonates is described under solvent‐free conditions at 100°C from reaction between aldehydes and amines in the presence of trialkyl phosphites using Al(H2PO4)3 as an efficient and reusable heterogeneous catalyst. The advantages of this procedure are short reaction time, flexibility and having high to excellent yields.

  描述了在无溶剂条件下，在亚磷酸三烷基酯存在下，使用Al（H 2 PO 4）3作为有效且可重复使用的多相催化剂，醛与胺之间的反应，在无溶剂条件下合成α-氨基膦酸酯的方法。该方法的优点是反应时间短，柔韧性好并且产率高至优异。
• Coupling of Aldehydes, Amines, and Trimethyl Phosphite Promoted by Amberlyst-15: Highly Efficient Synthesis of α-Aminophosphonates
  作者：Mahmood Tajbakhsh、Akbar Heydari、Heshmatollah Alinezhad、Mercedeh Ghanei、Samad Khaksar

  DOI：10.1055/s-2008-1032034

  日期：2008.2

  A three-component reaction promoted by Amberlyst-15 of an amine, an aldehyde, and trimethyl phosphite (Kabachnik-Fields reaction) in one pot under mild conditions affords the corresponding α-aminophosphonate in high yield after a short reaction time at ambient temperature.

  Amberlyst-15 在温和条件下在一锅中促进胺、醛和亚磷酸三甲酯的三组分反应（Kabachnik-Fields 反应），在环境温度下短反应时间后以高产率提供相应的 α-氨基膦酸酯。