methyl (E)-2-(2,4-dinitrobenzenesulfonylamino)hex-4-enoate | 1234564-07-8

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: methyl (E)-2-(2,4-dinitrobenzenesulfonylamino)hex-4-enoate
• CAS: 1234564-07-8
• 化学式: C₁₃H₁₅N₃O₈S
• 分子量: 373.343
• InChiKey: SHXBVWVBRJOJBA-ONEGZZNKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.29
• 重原子数：
  25.0
• 可旋转键数：
  8.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  158.75
• 氢给体数：
  1.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  methyl (E)-2-(2,4-dinitrobenzenesulfonylamino)hex-4-enoate 在 三氟甲磺酸 作用下， 以 氯仿 为溶剂， 反应 4.0h， 生成 methyl (2RS,5RS)-1-(2,4-dinitrobenzenesulfonyl)-5-methylpyrrolidine-2-carboxylate 、 methyl (2SR,5RS)-1-(2,4-dinitrobenzenesulfonyl)-5-methylpyrrolidine-2-carboxylate
  参考文献：
  名称：

  Carbenium ion trapping using sulfonamides: an acid-catalysed synthesis of pyrrolidines by intramolecular hydroamination

  摘要：

  Cyclisations of homoallylic sulfonamides proceed smoothly via carbenium ion generation using trifluoromethanesulfonic (triflic) acid, the ease of cyclisation being directly related to the ion stability to give good to excellent yields of the corresponding pyrrolidines. Both toluene- and nitrophenyl-sulfonyl groups are suitable for all substrates tested whereas the corresponding carbamates are only useful in cases of tertiary and highly stabilised carbenium ions. Polyene-derived sulfonamides can also be cyclised to the corresponding polycyclic systems in remarkably high yields, in reactions reminiscent of related cascades encountered in terpene biosynthesis. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2010.03.107
• 作为产物：
  描述：

  2,4-二硝基苯磺酰氯 、 Methyl (E)-2-aminohex-4-enoate 在 吡啶 、 4-二甲氨基吡啶 作用下， 以 氯仿 为溶剂， 以47%的产率得到methyl (E)-2-(2,4-dinitrobenzenesulfonylamino)hex-4-enoate
  参考文献：
  名称：

  Carbenium ion trapping using sulfonamides: an acid-catalysed synthesis of pyrrolidines by intramolecular hydroamination

  摘要：

  Cyclisations of homoallylic sulfonamides proceed smoothly via carbenium ion generation using trifluoromethanesulfonic (triflic) acid, the ease of cyclisation being directly related to the ion stability to give good to excellent yields of the corresponding pyrrolidines. Both toluene- and nitrophenyl-sulfonyl groups are suitable for all substrates tested whereas the corresponding carbamates are only useful in cases of tertiary and highly stabilised carbenium ions. Polyene-derived sulfonamides can also be cyclised to the corresponding polycyclic systems in remarkably high yields, in reactions reminiscent of related cascades encountered in terpene biosynthesis. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2010.03.107