N-benzyl-N-tert-butoxycarbonyl-4-cyanobenzenesulfonamide | 170948-02-4

• 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: N-benzyl-N-tert-butoxycarbonyl-4-cyanobenzenesulfonamide
• 英文别名: tert-butyl N-benzyl-N-(4-cyanophenyl)sulfonylcarbamate
• CAS: 170948-02-4
• 化学式: C₁₉H₂₀N₂O₄S
• 分子量: 372.445
• InChiKey: UENIPCNPEOXGNX-UHFFFAOYSA-N

物化性质

• 沸点：
  523.3±60.0 °C(Predicted)
• 密度：
  1.29±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  26
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  95.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  N-benzyl-N-tert-butoxycarbonyl-4-cyanobenzenesulfonamide 在 甲醇 、 magnesium 作用下， 反应 0.33h， 以100%的产率得到苄基-氨基甲酸叔丁酯
  参考文献：
  名称：

  Mild, efficient cleavage of arenesulfonamides by magnesium reduction

  摘要：

  在无水甲醇中，使用镁与N-芳基磺酰氨基碳酸酯的反应，在超声波条件下实现了芳基磺酰胺的裂解，仅需几分钟。

  DOI：

  10.1039/a701408b
• 作为产物：
  描述：

  N-苄基-4-溴苯磺酰胺 在 4-二甲氨基吡啶 作用下， 以 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 18.0h， 生成 N-benzyl-N-tert-butoxycarbonyl-4-cyanobenzenesulfonamide
  参考文献：
  名称：

  Synthesis and cathodic cleavage of a set of substituted benzenesulfonamides including the corresponding tert-butyl sulfonylcarbamates: pK a of sulfonamides

  摘要：

  From a series of Substituted benzenesulfonic acids, most of which have previously been employed for the protection of amino functions and including a few such known to facilitate cleavage by acid, benzylamides 1a-k have been derived and studied. Initially their electrochemical cleavage potentials were determined by cyclic voltammetry in order to further explore selective deprotection within this substance group. In parallel, the corresponding tert-butyl sulfonylcarbamates 2a-k have also been prepared and studied. Among the sulfonamides investigated S-N bond cleavage was found to take place over a wide range of potentials from -1.67 to -2.64 V (excluding the nitro derivative), the most acid-labile groups requiring more negative potentials, whereas this cleavage was facilitated by 0.19-0.30 V for the sulfonylcarbamates. Small scale electrolyses of 2 at controlled potential with determination of the cleavage products formed were subsequently performed. For the N-benzylbenzenesulfonamides 1, the pK(a)s in DMSO and in some cases also in water have been determined and found to be in the range 14.0-16.4 and 10.07-11.53, respectively.

  DOI：

  10.1039/p19950002025

文献信息

• Synthesis and cathodic cleavage of a set of substituted benzenesulfonamides including the corresponding tert-butyl sulfonylcarbamates: pK a of sulfonamides
  作者：Barth�l�my Nyasse、Leif Grehn、Ulf Ragnarsson、Hernani L. S. Maia、Luis S. Monteiro、Ivo Leito、Ilmar Koppel、Juta Koppel

  DOI：10.1039/p19950002025

  日期：——

  From a series of Substituted benzenesulfonic acids, most of which have previously been employed for the protection of amino functions and including a few such known to facilitate cleavage by acid, benzylamides 1a-k have been derived and studied. Initially their electrochemical cleavage potentials were determined by cyclic voltammetry in order to further explore selective deprotection within this substance group. In parallel, the corresponding tert-butyl sulfonylcarbamates 2a-k have also been prepared and studied. Among the sulfonamides investigated S-N bond cleavage was found to take place over a wide range of potentials from -1.67 to -2.64 V (excluding the nitro derivative), the most acid-labile groups requiring more negative potentials, whereas this cleavage was facilitated by 0.19-0.30 V for the sulfonylcarbamates. Small scale electrolyses of 2 at controlled potential with determination of the cleavage products formed were subsequently performed. For the N-benzylbenzenesulfonamides 1, the pK(a)s in DMSO and in some cases also in water have been determined and found to be in the range 14.0-16.4 and 10.07-11.53, respectively.
• Mild, efficient cleavage of arenesulfonamides by magnesium reduction
  作者：Barthélémy Nyasse、Leif Grehn、Ulf Ragnarsson

  DOI：10.1039/a701408b

  日期：——

  The cleavage of arenesulfonamides via N-arenesulfonylcarbamates is achieved within a few minutes under ultrasonic conditions by reaction with magnesium in anhydrous methanol.

  在无水甲醇中，使用镁与N-芳基磺酰氨基碳酸酯的反应，在超声波条件下实现了芳基磺酰胺的裂解，仅需几分钟。