diisopropyl ((4-bromophenyl)(phenylamino)methyl)phosphonate

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: diisopropyl ((4-bromophenyl)(phenylamino)methyl)phosphonate
• 英文别名: N-[(4-bromophenyl)-di(propan-2-yloxy)phosphorylmethyl]aniline
• 化学式: C₁₉H₂₅BrNO₃P
• 分子量: 426.29
• InChiKey: UGNBPKCZFUMXHW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  25
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.37
• 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：

  亚磷酸二异丙酯 、 N-(4-bromobenzylidene)aniline 在 水 作用下， 以 异丙醇 为溶剂， 生成 diisopropyl ((4-bromophenyl)(phenylamino)methyl)phosphonate
  参考文献：
  名称：

  Kinetics and mechanism of the Pudovik reaction in the azomethine series: III. Acid-catalyzed hydrophosphorylation of imines

  摘要：

  A complex spectral (UV, IR, and P-31 NMR), preparative, and kinetic investigation of the mechanism of the noncatalytic variant of the Pudovik reaction in the series of imines was carried out. The reaction proceeds through a four-center cyclic transition state. The transition state is highly labile, which determines its high sensitivity to the structure of the reagents, the nature of the solvent and catalyst, and some other factors. The necessary condition for the hydrophosphorylation of imines to occur is the participation of proton-donor reagents and acidic admixtures, specifically hydrolysis products of dialkyl hydrogen phosphites, such as monoalkyl dihydrogen phosphates and phosphorous acid, which act as acid catalysts. When the starting, reagents are thoroughly purified and no such catalysts are present, the Pudovik reaction fails to occur in the imine series.

  DOI：

  10.1134/s1070363206030121

文献信息

• α-Aminophosphonates 4-XC6H4–NH–CH(4-BrC6H4)–P(O)(OiPr)2 (X = H, Br, MeO): Crystal structures, Hirshfeld surface analysis, computational studies and in silico molecular docking with the SARS-CoV-2 proteins
  作者：Larisa E. Alkhimova、Maria G. Babashkina、Damir A. Safin

  DOI：10.1016/j.tet.2021.132376

  日期：2021.9

  We report structural and computational studies of three α-aminophosphonates 4-XC6H4–NH–CH(4-BrC6H4)–P(O)(OiPr)2, namely diisopropyl((4-bromophenyl)(phenylamino)methyl)phosphonate (X = H, 1), diisopropyl((4-bromophenyl)((4-bromophenyl)amino)methyl)phosphonate (X = Br, 2) and diisopropyl((4-bromophenyl)((4-methoxyphenyl)amino)methyl)phosphonate (X = MeO, 3). The structures of 1–3 were fully confirmed

  我们报告了三种α-氨基膦酸酯 4-XC 6 H 4 –NH–CH(4-BrC 6 H 4 )–P(O)(O i Pr) 2的结构和计算研究，即二异丙基((4-溴苯基)(苯氨基)甲基)膦酸酯 (X = H, 1 )、二异丙基((4-溴苯基)((4-溴苯基)氨基)甲基)膦酸酯 (X = Br, 2 ) 和二异丙基((4-溴苯基)((4-甲氧基苯基)氨基)甲基)膦酸酯(X = MeO, 3 )。 1-3的结构通过31 P 1 H }和1 H NMR 光谱得到充分证实。 2和3的晶体结构是同构的，并且各自在不对称晶胞中包含两个独立的分子。能量框架已被计算以分析1 – 3的整体晶体堆积。进行DFT计算以验证1-3的结构及其电子和光学性质。应用分子对接来检查1 – 3的 ( S )-和 ( R )-对映体对一系列 SARS-CoV-2 蛋白的影响。