(S)-1-(2,4-dinitrophenyl)-3-(3-hydroxy-2-(3-methoxy-2-nitrobenzamido)propyl)pyridinium chloride | 1233705-45-7

• 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: (S)-1-(2,4-dinitrophenyl)-3-(3-hydroxy-2-(3-methoxy-2-nitrobenzamido)propyl)pyridinium chloride
• 英文别名: N-[(2S)-1-[1-(2,4-dinitrophenyl)pyridin-1-ium-3-yl]-3-hydroxypropan-2-yl]-3-methoxy-2-nitrobenzamide;chloride
• CAS: 1233705-45-7
• 化学式: C₂₂H₂₀N₅O₉*Cl
• 分子量: 533.882
• InChiKey: FEDDKFHCYPPOQL-RSAXXLAASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.97
• 重原子数：
  37
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  200
• 氢给体数：
  2
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  (S)-1-(2,4-dinitrophenyl)-3-(3-hydroxy-2-(3-methoxy-2-nitrobenzamido)propyl)pyridinium chloride 、 叔丁基二甲基氯硅烷 在 咪唑 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 生成
  参考文献：
  名称：

  Concise Formal Synthesis of Porothramycins A and B via Zincke Pyridinium Ring-Opening/Ring-Closing Cascade

  摘要：

  Short formal syntheses of the antitumor antibiotics porothramycins A and B from a commercially available ester of the unnatural amino acid 3-(3-pyridyl)alanine are presented. A rearrangement cascade that presumably involves a Zincke-type pyridinium ring-opening followed by cyclization of a pendant nucleophilic amide generates the salient pyrroline ring of the alkaloids.

  DOI：

  10.1021/ol101035p
• 作为产物：
  描述：

  (S)-N-(1-hydroxy-3-(pyridin-3-yl)propan-2-yl)-3-methoxy-2-nitrobenzamide 、 1-氯-2,4-二硝基苯 以 仲丁醇 为溶剂， 反应 12.0h， 以64%的产率得到(S)-1-(2,4-dinitrophenyl)-3-(3-hydroxy-2-(3-methoxy-2-nitrobenzamido)propyl)pyridinium chloride
  参考文献：
  名称：

  Concise Formal Synthesis of Porothramycins A and B via Zincke Pyridinium Ring-Opening/Ring-Closing Cascade

  摘要：

  Short formal syntheses of the antitumor antibiotics porothramycins A and B from a commercially available ester of the unnatural amino acid 3-(3-pyridyl)alanine are presented. A rearrangement cascade that presumably involves a Zincke-type pyridinium ring-opening followed by cyclization of a pendant nucleophilic amide generates the salient pyrroline ring of the alkaloids.

  DOI：

  10.1021/ol101035p

文献信息

• Concise Formal Synthesis of Porothramycins A and B via Zincke Pyridinium Ring-Opening/Ring-Closing Cascade
  作者：Theo D. Michels、Matthew J. Kier、Aaron M. Kearney、Christopher D. Vanderwal

  DOI：10.1021/ol101035p

  日期：2010.7.2

  Short formal syntheses of the antitumor antibiotics porothramycins A and B from a commercially available ester of the unnatural amino acid 3-(3-pyridyl)alanine are presented. A rearrangement cascade that presumably involves a Zincke-type pyridinium ring-opening followed by cyclization of a pendant nucleophilic amide generates the salient pyrroline ring of the alkaloids.