N-acetyl ethanesulfonamide | 89123-24-0

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机磺酸及其衍生物
• 英文名称: N-acetyl ethanesulfonamide
• 英文别名: N-ethanesulfonyl-acetamide；N-Aethansulfonyl-acetamid；N-Acetyl-aethansulfonamid；N-ethylsulfonylacetamide
• CAS: 89123-24-0
• 化学式: C₄H₉NO₃S
• 分子量: 151.186
• InChiKey: XVHXRGOONYQMJK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.5
• 重原子数：
  9
• 可旋转键数：
  2
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  71.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  N-acyl N-benzyl ethanesulfonamide 在 palladium dihydroxide 氢气 作用下， 以 乙醇 为溶剂， 反应 14.0h， 以83%的产率得到N-acetyl ethanesulfonamide
  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

文献信息

• Kosstzowa, Zhurnal Obshchei Khimii, 1948, vol. 18, p. 731
  作者：Kosstzowa

  DOI：——

  日期：——
• 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.