N-benzyl-N-(benzyloxycarbonyl) toluenesulfonamide | 147357-85-5

• 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-(benzyloxycarbonyl) toluenesulfonamide
• 英文别名: benzyl N-benzyl-N-(4-methylphenyl)sulfonylcarbamate
• CAS: 147357-85-5
• 化学式: C₂₂H₂₁NO₄S
• 分子量: 395.479
• InChiKey: XLIJDUZIXJFBLF-UHFFFAOYSA-N

物化性质

• 沸点：
  553.0±60.0 °C(Predicted)
• 密度：
  1.264±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  28
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  72.1
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-benzyl-N-(benzyloxycarbonyl) toluenesulfonamide 在 palladium dihydroxide palladium dihydroxide 、 氢气 作用下， 以 乙醇 为溶剂， 生成 对甲苯磺酰胺
  参考文献：
  名称：

  A reversible safety-catch method for the hydrogenolysis of N-benzyl moieties

  摘要：

  The benzyl groups of beta-hydroxy-N-benzyl sulfonamides are labile toward hydrogenolysis-unlike N-benzyl sulfonamides lacking the beta-hydroxy moiety. We find that N-acyl-N-benzyl sulfonamides undergo hydrogenolysis under very mild conditions. Based upon these observations, we developed a reversible safety-catch method using tert-butoxycarbonyl moieties to activate N-benzyl sulfonamides toward hydrogenolysis. We also explored the utility of the safety-catch activation method for other nitrogen-based functionality such as N-benzyl carboxamides, imides, and related functionality. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2004.09.118
• 作为产物：
  描述：

  N-benzyl-p-toluenesulfonamide 、 氯甲酸苄酯 在 4-二甲氨基吡啶 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 以73%的产率得到N-benzyl-N-(benzyloxycarbonyl) toluenesulfonamide
  参考文献：
  名称：

  Maia, Hernani L. S.; Monteiro, Luis S.; Degerbeck, Fredrik, Journal of the Chemical Society. Perkin transactions II, 1993, # 3, p. 495 - 500

  摘要：

  DOI：

文献信息

• A reversible safety-catch method for the hydrogenolysis of N-benzyl moieties
  作者：David C. Johnson、Theodore S. Widlanski

  DOI：10.1016/j.tetlet.2004.09.118

  日期：2004.11

  The benzyl groups of beta-hydroxy-N-benzyl sulfonamides are labile toward hydrogenolysis-unlike N-benzyl sulfonamides lacking the beta-hydroxy moiety. We find that N-acyl-N-benzyl sulfonamides undergo hydrogenolysis under very mild conditions. Based upon these observations, we developed a reversible safety-catch method using tert-butoxycarbonyl moieties to activate N-benzyl sulfonamides toward hydrogenolysis. We also explored the utility of the safety-catch activation method for other nitrogen-based functionality such as N-benzyl carboxamides, imides, and related functionality. (C) 2004 Elsevier Ltd. All rights reserved.
• Maia, Hernani L. S.; Monteiro, Luis S.; Degerbeck, Fredrik, Journal of the Chemical Society. Perkin transactions II, 1993, # 3, p. 495 - 500
  作者：Maia, Hernani L. S.、Monteiro, Luis S.、Degerbeck, Fredrik、Grehn, Leif、Ragnarsson, Ulf

  DOI：——

  日期：——