dimethyl (((4-chlorophenyl)amino)(phenyl)methyl)phosphonate | 141380-78-1

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: dimethyl (((4-chlorophenyl)amino)(phenyl)methyl)phosphonate
• 英文别名: [(4-Chloro-phenylamino)-phenyl-methyl]-phosphonic acid dimethyl ester；4-chloro-N-[dimethoxyphosphoryl(phenyl)methyl]aniline
• CAS: 141380-78-1
• 化学式: C₁₅H₁₇ClNO₃P
• 分子量: 325.732
• InChiKey: KONUECVLMWQWKY-UHFFFAOYSA-N

物化性质

• 沸点：
  476.3±40.0 °C(Predicted)
• 密度：
  1.291±0.06 g/cm3(Predicted)
• 溶解度：
  >48.9 [ug/mL]

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  21
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  47.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  苯甲醛 在 sodium tetrahydroborate 、 sodium ethanolate 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 4.0h， 生成 dimethyl (((4-chlorophenyl)amino)(phenyl)methyl)phosphonate
  参考文献：
  名称：

  通过使用2,3-二氯-5,6-二氰基苯并醌使仲N-烷基苯胺的膦酸酯化和氰化的交叉脱氢偶联策略

  摘要：

  首先在温和的反应条件下开发了无金属的膦酸和仲N-烷基苯胺氰化的交叉脱氢偶联策略。在详细优化反应条件的基础上，研究了N-烷基苯胺和各种膦酸氢盐的底物通用性，因此提供了一系列通用的α-氨基膦酸酯和α-氨基腈，收率良好至优异。提出了通过脱氢形成亚胺，然后分别形成α-氨基膦酸酯和α-氨基腈的合理的集体反应机理。

  DOI：

  10.1016/j.tet.2018.10.058

文献信息

• Formic acid catalyzed one-pot synthesis of α-aminophosphonates: an efficient, inexpensive and environmental friendly organocatalyst
  作者：Jamshid Azarnia Mehraban、Mahsa Sadat Jalali、Akbar Heydari

  DOI：10.1007/s11696-018-0434-6

  日期：2018.9

  AbstractAqueous formic acid is used for the synthesis of α-aminophosphonates through Kabachnik–Fields reaction applying aromatic amine, phosphite, and carbonyl compounds. Using formic acid as an efficient and low-cost organocatalyst provides environmental friendly, high yields, low reaction time and mild reaction condition. The isolated products were analyzed by IR, NMR, and mass techniques. Graphical

  摘要甲酸水溶液通过Kabachnik-Fields反应（使用芳香胺，亚磷酸酯和羰基化合物）用于合成α-氨基膦酸酯。使用甲酸作为一种高效且低成本的有机催化剂可提供环保，高产率，短反应时间和温和的反应条件。通过IR，NMR和质量技术分析分离的产物。 图形概要
• One-Pot Synthesis of Dialkyl Arylaminomethyl- and (Arylamino)arylmethylphosphonates and Their<i>N</i>-Acylated Derivatives
  作者：L. K. Lukanov、A. P. Venkov

  DOI：10.1055/s-1992-26083

  日期：——

  A convenient synthesis of dialkyl arylaminomethyl- and (arylamino) arylmethylphosphonates 3 and their N-acylated derivatives 5 have been developed, starting from azomethines and phosphorus trichloride in the presence of an alcohol.

  开发了一种便利的合成方法，以醛基取代的二烷基芳基氨基甲基磷酸酯 3 及其 N-酰化衍生物 5 为目标，反应从亚胺和三氯化磷在醇的存在下开始。
• N–H insertion reactions of rhodium carbenoids. Part 1. Preparation of α-amino acid and α-aminophosphonic acid derivatives
  作者：Enrique Aller、Richard T. Buck、Martin J. Drysdale、Leigh Ferris、David Haigh、Christopher J. Moody、Neil D. Pearson、J. Bobby Sanghera

  DOI：10.1039/p19960002879

  日期：——

  Rhodium(II) acetate-catalysed decomposition of diazophenylacetates 1 and 3 in the presence of a range of N–H compounds results in an N–H insertion reaction of the intermediate carbenoids and formation of N-substituted phenylglycine derivatives 2 and 4. The corresponding reactions of dimethyl α-diazobenzylphosphonate 5 constitute a simple route to aminophosphonates 6.

  在一定范围的N–H化合物存在下，乙酸铑（II）催化的重氮苯基乙酸酯1和3的分解导致中间类胡萝卜素的N–H插入反应并形成N-取代的苯基甘氨酸衍生物2和4。 α-二重氮苄基膦酸二甲酯5的反应构成了氨基膦酸酯6的简单路线。
• 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。
• Cobalt(II) chloride accelerated one-pot three-component synthesis of α-aminophosphonates at room temperature
  作者：Zahed Karimi-Jaberi、Hassan Zare、Mohammad Amiri、Naghmeh Sadeghi

  DOI：10.1016/j.cclet.2010.11.034

  日期：2011.5

  efficient, and general method has been developed for the one-pot, three-component synthesis of α-aminophosphonates from condensation reaction of trimethyl phosphite, aryl aldehydes and aryl amines in the presence of CoCl 2 ·6H 2 O under solvent-free conditions. Thus α -aminophosphonates were synthesized relatively quickly in good yields at room temperature.

  摘要研究了在溶剂中CoCl 2·6H 2 O存在下，由亚磷酸三甲酯，芳基醛和芳基胺的缩合反应一锅三组分合成α-氨基膦酸酯的简便，通用的方法。无条件。因此，α-氨基膦酸酯在室温下以相对高的产率相对较快地合成。