dimethyl (cyclohexyl(phenylamino)methyl)phosphonate

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: dimethyl (cyclohexyl(phenylamino)methyl)phosphonate
• 英文别名: Dimethyl [anilino(cyclohexyl)methyl]phosphonate；N-[cyclohexyl(dimethoxyphosphoryl)methyl]aniline
• 化学式: C₁₅H₂₄NO₃P
• 分子量: 297.334
• InChiKey: JGZXNJWMYSJSNC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  20
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.6
• 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：

  N-phenyl-1-(cyclohexyl)methanimine 在 sodium tetrahydroborate 、 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 (cyclohexyl(phenylamino)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
• α-Aminophosphonates as novel anti-leishmanial chemotypes: synthesis, biological evaluation, and CoMFA studies
  作者：Srikant Bhagat、Parth Shah、Sanjeev K. Garg、Shweta Mishra、Preet Kamal Kaur、Sushma Singh、Asit K. Chakraborti

  DOI：10.1039/c3md00388d

  日期：——

  α-Aminophosphonates have been identified as novel anti-leishmanial chemotypes against theL. donovanipromastigote with low μM range activity.

  α-氨基膦酸酯已被确定为针对L. donovani原虫具有低微米范围活性的新型抗利什曼病化合物。
• Highly efficient synthesis of α-aminophosphonates catalyzed by hafnium(IV) chloride
  作者：Xiao-Chuan Li、Shan-Shan Gong、De-Yun Zeng、Yue-Hai You、Qi Sun

  DOI：10.1016/j.tetlet.2016.03.033

  日期：2016.4

  A highly efficient one-pot method for the synthesis of a variety of α-aminophosphonates via the one-pot three-component reaction of aldehyde, amine, and phosphite has been developed using only 2 mol % HfCl4 as the catalyst. The NMR evidence strongly indicated the catalytic roles of Hf(IV) on the activation of aldehyde, phosphite, and imine intermediate.

  已经开发出仅使用2mol％的HfCl 4作为催化剂通过醛，胺和亚磷酸酯的一锅三组分反应来合成各种α-氨基膦酸酯的高效一锅法。NMR证据强烈表明Hf（IV）对醛，亚磷酸酯和亚胺中间体的活化具有催化作用。
• Ultrasonic and Lewis acid ionic liquid catalytic system for Kabachnik-Fields reaction
  作者：Sadegh Rostamnia、Mojtaba Amini

  DOI：10.2478/s11696-013-0516-4

  日期：2014.1.1

  A combination of ultrasonic (US) and [bmim]AlCl4 ionic liquid is used as an alternative to conventional acid catalysts in the Kabachnik-Fields reaction of an amine and aryl aldehyde with phosphite leading to the formation of aminophosphonates. The reaction time was significantly reduced and the reaction progressed very smoothly.

  摘要：在Kabachnik-Fields反应中，将超声波（US）和[bmim]AlCl4离子液体组合使用作为传统酸催化剂的替代品，反应胺和芳香醛与亚磷酸酯形成氨基膦酸盐。反应时间显著缩短，反应进行非常顺利。
• Cross-dehydrogenative coupling strategy for phosphonation and cyanation of secondary N-alkyl anilines by employing 2,3-dichloro-5,6-dicyanobenzoquinone
  作者：Qing Liu、Shuchen Yu、Liangzhen Hu、Muhamad Ijaz Hussain、Xiaohui Zhang、Yan Xiong

  DOI：10.1016/j.tet.2018.10.058

  日期：2018.12

  has been developed firstly under mild reaction conditions. Based on detailed optimization of reaction conditions, the substrate generality of N-alkyl anilines and various hydrogen phosphonates has been investigated, and a series of versatile α-aminophosphonates and α-aminonitriles were therefore furnished in good to excellent yields. A plausible collective reaction mechanism through dehydrogenation to

  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。