2-nitro-N-(4-nitrobenzylidene)-benzenesulfonamide | 1026867-81-1

• 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: 2-nitro-N-(4-nitrobenzylidene)-benzenesulfonamide
• 英文别名: (NE)-2-nitro-N-[(4-nitrophenyl)methylidene]benzenesulfonamide
• CAS: 1026867-81-1
• 化学式: C₁₃H₉N₃O₆S
• 分子量: 335.297
• InChiKey: LADMWRFYVSEFFS-NTEUORMPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  23
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  147
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  2-nitro-N-(4-nitrobenzylidene)-benzenesulfonamide 、 丁烯酮 在 bis(1,5-cyclooctadiene)rhodium(I) trifluoromethanesulfonate 三(2-呋喃基)膦 、 氘 作用下， 以 1,2-二氯乙烷 为溶剂， 35.0 ℃ 、101.33 kPa 条件下， 生成 N-[(1R,2R)-2-(deuteriomethyl)-1-(4-nitrophenyl)-3-oxobutyl]-2-nitrobenzenesulfonamide 、
  参考文献：
  名称：

  Rhodium-Catalyzed Reductive Mannich Coupling of Vinyl Ketones to N-Sulfonylimines Mediated by Hydrogen

  摘要：

  Catalytic hydrogenation of methyl vinyl ketone (MVK) and ethyl vinyl ketone (EVK) in the presence of N-(o-nitrophenylsulfonyl)imines 8a-13a at ambient pressure with tri-2-furylphosphine-ligated rhodium catalysts enables formation of Mannich products 8b-13b and 8c-13c with moderate to good levels of syn-diastereoselectivity. As revealed by an assay of various N-protecting groups, excellent yields of reductive Mannich product also are obtained for N-arylimines 1a-4a, although diminished levels of syn-diastereoselectivity are observed. Coupling of MVK to imine 8a under a deuterium atmosphere provides deuterio-8b, which incorporates a single deuterium atom at the former enone beta-position.

  DOI：

  10.1021/jo070779w
• 作为产物：
  描述：

  2-硝基苯磺酰胺 、 对硝基苯甲醛 在 硅酸四乙酯 作用下， 反应 6.0h， 生成 2-nitro-N-(4-nitrobenzylidene)-benzenesulfonamide
  参考文献：
  名称：

  Rhodium-Catalyzed Reductive Mannich Coupling of Vinyl Ketones to N-Sulfonylimines Mediated by Hydrogen

  摘要：

  Catalytic hydrogenation of methyl vinyl ketone (MVK) and ethyl vinyl ketone (EVK) in the presence of N-(o-nitrophenylsulfonyl)imines 8a-13a at ambient pressure with tri-2-furylphosphine-ligated rhodium catalysts enables formation of Mannich products 8b-13b and 8c-13c with moderate to good levels of syn-diastereoselectivity. As revealed by an assay of various N-protecting groups, excellent yields of reductive Mannich product also are obtained for N-arylimines 1a-4a, although diminished levels of syn-diastereoselectivity are observed. Coupling of MVK to imine 8a under a deuterium atmosphere provides deuterio-8b, which incorporates a single deuterium atom at the former enone beta-position.

  DOI：

  10.1021/jo070779w