N-tert-butoxycarbonyl-N-tosyl-N'-benzyloxycarbonyl-1,2-ethylenediamine | 192320-25-5

• 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-tert-butoxycarbonyl-N-tosyl-N'-benzyloxycarbonyl-1,2-ethylenediamine
• 英文别名: tert-butyl N-(4-methylphenyl)sulfonyl-N-[2-(phenylmethoxycarbonylamino)ethyl]carbamate
• CAS: 192320-25-5
• 化学式: C₂₂H₂₈N₂O₆S
• 分子量: 448.54
• InChiKey: YQDLWSRKKGYYBN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  31
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  110
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  N-tert-butoxycarbonyl-N-tosyl-N'-benzyloxycarbonyl-1,2-ethylenediamine 在 甲醇 、 magnesium 作用下， 反应 0.33h， 以99%的产率得到N-Cbz-N’-Boc-乙二胺
  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-甲苯磺酰基乙二胺 在 4-二甲氨基吡啶 作用下， 以 吡啶 、 乙腈 为溶剂， 反应 5.0h， 生成 N-tert-butoxycarbonyl-N-tosyl-N'-benzyloxycarbonyl-1,2-ethylenediamine
  参考文献：
  名称：

  Chemoselective Substitution in 4-Toluenesulfonamides and Carbamates by Di-tert-butyl Dicarbonate in the Presence of 4-Dimethylaminopyridine.

  摘要：

  Three novel derivatives of 1,2-ethylenediamine 1, 3 and 5 with 4-toluenesulfonyl and/or carbamate moieties have been prepared and submitted to reaction with a limiting amount of di-tert-butyl dicarbonate in the presence of catalytic amounts of 4-dimethylaminopyridine. All the reagents underwent completely selective substitution under these conditions and gave rise to the products 2a, 4 and 6 in 93-100% yields and the results were rationalized in terms of higher NH-acidity at the reaction sites. The products might be useful in synthesis of substituted 1,2-ethylenediamines. A similar approach might be applicable to many other diamines.

  DOI：

  10.3891/acta.chem.scand.52-0627

文献信息

• 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。
• Chemoselective Substitution in 4-Toluenesulfonamides and Carbamates by Di-tert-butyl Dicarbonate in the Presence of 4-Dimethylaminopyridine.
  作者：Leif Grehn、Ulf Ragnarsson、Anders Kjær、Carl E. Olsen、Birgitte R. Rassing、Connie N. Rosendahl、Inger Søtofte、Bengt Långström

  DOI：10.3891/acta.chem.scand.52-0627

  日期：——

  Three novel derivatives of 1,2-ethylenediamine 1, 3 and 5 with 4-toluenesulfonyl and/or carbamate moieties have been prepared and submitted to reaction with a limiting amount of di-tert-butyl dicarbonate in the presence of catalytic amounts of 4-dimethylaminopyridine. All the reagents underwent completely selective substitution under these conditions and gave rise to the products 2a, 4 and 6 in 93-100% yields and the results were rationalized in terms of higher NH-acidity at the reaction sites. The products might be useful in synthesis of substituted 1,2-ethylenediamines. A similar approach might be applicable to many other diamines.