diethyl [α-(N-tosylamino)-4-methoxybenzyl]phosphonate | 79819-60-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: diethyl [α-(N-tosylamino)-4-methoxybenzyl]phosphonate
• 英文别名: α-diethoxyphosphoryl-p-methoxy-N-tosylbenzamine；(±)-diethyl (4-methoxyphenyl)(4-methylphenylsulfonamido)methylphosphonate；diethyl ((4-methoxyphenyl)(4-methylphenylsulfonamido)methyl)phosphonate；N-[diethoxyphosphoryl-(4-methoxyphenyl)methyl]-4-methylbenzenesulfonamide
• CAS: 79819-60-6
• 化学式: C₁₉H₂₆NO₆PS
• 分子量: 427.458
• InChiKey: YXHIZSVBSFLCAM-UHFFFAOYSA-N

物化性质

• 熔点：
  114-115 °C
• 沸点：
  574.0±60.0 °C(Predicted)
• 密度：
  1.240±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  28
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  99.3
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  diethyl [α-(N-tosylamino)-4-methoxybenzyl]phosphonate 在 potassium carbonate 作用下， 以 甲醇 、 丙酮 为溶剂， 反应 32.0h， 生成 N-benzyl-α-diethylphosphoryl-p-methoxybenzylimine
  参考文献：
  名称：

  从磺酰胺中除去甲苯-对-磺酰基。第5部分。苯乙二醛亚胺和一些甲苯磺胺的反应

  摘要：

  苯乙二醛茴香醚单体已显示出与几种亲核试剂反应，并且已经阐明了产物的结构。各种N-甲苯磺酰基嘧啶也与亲核试剂反应以产生有用的产物。苯乙酰亚胺与二苯甲酮进行[2 + 2]个环加成；此类反应与苯乙酰亚胺类化合物产生复杂的结果，但后者在BF 3的存在下与共轭二烯反应，以高收率得到[2 + 4]环加成产物。

  DOI：

  10.1039/p19810002443
• 作为产物：
  描述：

  (E)-N-(4-methoxybenzylidene)-4-methylbenzenesulfonamide 、 亚磷酸二乙酯 以76%的产率得到
  参考文献：
  名称：

  MCKAY, W. R.;PROCTOR, G. R., J. CHEM. SOC. PERKIN TRANS., 1981, N 9, 2443-2450

  摘要：

  DOI：

文献信息

• Triflic acid mediated functionalization of α-hydroxyphosphonates: route for sulfonamide phosphonates
  作者：Gangaram Pallikonda、Manab Chakravarty

  DOI：10.1039/c3ra43823f

  日期：——

  An operationally simple synthetic method for (±)-α-aryl/methylsulfonamidomethylphosphonates and new (±)-γ-aryl/methyl sulfonamidomethylvinylphosphonates has been developed through straightforward reactions of (±)-α-hydroxyphosphonates with sulfonamides in the presence of triflic acid (TfOH) at room temperature in a vessel open to air. For γ-dimethylallylhydroxyphosphonate, the (E)-1,3-butadienylphosphonate was formed quantitatively using TfOH while FeCl3 afforded the expected product in moderate yield unpredictably. The favourable sulfonoamidation of benzyl alcohol is also observed when TfOH was used for α-hydroxyphosphonates having a benzyloxy group.

  通过在室温下，在三氟甲磺酸（TfOH）存在下，将（±）-α-羟基膦酸与磺酰胺在开放容器中进行简单反应，开发了一种用于合成（±）-α-芳基/甲基磺酰胺甲基膦酸酯和新型（±）-γ-芳基/甲基磺酰胺甲基乙烯基膦酸酯的操作简便的合成方法。对于γ-二甲基烯丙基羟基膦酸，TfOH定量地形成（E）-1,3-丁二烯基膦酸，而FeCl3则以中等产率不可预测地得到了预期产物。当TfOH用于含有苄氧基的α-羟基膦酸时，也观察到苄醇的有利磺酰胺化。
• Sigmatropic isomerizations in azaallyl systems: XX. N-Alkylbenzimidoylphosphonates
  作者：P. P. Onys’ko、T. V. Kim、Yu. V. Rassukanaya、E. I. Kiseleva、A. D. Sinitsa

  DOI：10.1007/s11176-005-0007-6

  日期：2004.9

  Synthetic approaches are developed to benzimidoylphosphoryl derivatives containing electronically and sterically diverse alkyl substituents on the nitrogen atom, as well as their prototropic isomers. Regularities in prototropic transitions in the phosphorylated C=N-C triad were revealed and applied in the synthesis of α-aminophosphonic acid derivatives.

  开发了合成方法以制备含有电子和立体多样的烷基取代基的苯并咪唑基磷酸酯衍生物，以及它们的质子化异构体。揭示了磷酸化C=N-C三元组中的质子转移规律，并应用于α-氨基磷酸衍生物的合成。
• α-Sulfonamidophosphonates as new anti-mycobacterial chemotypes: Design, development of synthetic methodology, and biological evaluation
  作者：Srikant Bhagat、Metheku Supriya、Satish Pathak、Dharmarajan Sriram、Asit K. Chakraborti

  DOI：10.1016/j.bioorg.2018.09.023

  日期：2019.2

  Tuberculosis (TB) is the leading cause of death worldwide due to bacterial infection. The scarcity of effective drugs to treat the disease and the compounded problems due to the development of resistance to the available therapeutics and TB-HIV synergism drive medicinal chemists to search for new anti-Mtb chemotypes. Towards this endeavor, the alpha-sulfonamidophosphonate moiety has been identified as new anti-Mtb chemotype through the scaffold hopping as the design strategy, development of an effective synthetic methodology using green chemistry tools, and evaluation of anti-TB activity of the synthesized compounds against Mtb (Mycobacterium tuberculosis) H37Rv. Out of the sixteen compounds, five have been found to have MIC values of 1.56 mu g/mL and one 3.125 mu g/mL. The five most active compounds are non-cytotoxic to RAW 264.7 (mouse leukemic monocyte macrophage) cell lines. The compounds are found to possess acceptable values of the various parameters for drug likeness in accordance with the Lipinski rule with the topological surface area (tPSA) of > 70 that suggest eligibility of these new molecular entities for further consideration as potential drug candidates.