(E)-3-[(S)-5-((tert-butyldimethylsilyloxy)methyl)-1-(3-methoxy-2-nitrobenzoyl)-4,5-dihydro-1H-pyrrol-3-yl]-N,N-dimethylacrylamide | 1233705-47-9

• 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: (E)-3-[(S)-5-((tert-butyldimethylsilyloxy)methyl)-1-(3-methoxy-2-nitrobenzoyl)-4,5-dihydro-1H-pyrrol-3-yl]-N,N-dimethylacrylamide
• 英文别名: (E)-3-[(2S)-2-[[tert-butyl(dimethyl)silyl]oxymethyl]-1-(3-methoxy-2-nitrobenzoyl)-2,3-dihydropyrrol-4-yl]-N,N-dimethylprop-2-enamide
• CAS: 1233705-47-9
• 化学式: C₂₄H₃₅N₃O₆Si
• 分子量: 489.644
• InChiKey: LWBOYFDRGXCMLH-HHNLSAEISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.37
• 重原子数：
  34
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  105
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (E)-3-[(S)-5-((tert-butyldimethylsilyloxy)methyl)-1-(3-methoxy-2-nitrobenzoyl)-4,5-dihydro-1H-pyrrol-3-yl]-N,N-dimethylacrylamide 在 盐酸 作用下， 以 甲醇 、 水 为溶剂， 反应 2.0h， 以70%的产率得到(E)-3-[(S)-5-(hydroxymethyl)-1-(3-methoxy-2-nitrobenzoyl)-4,5-dihydro-1H-pyrrol-3-yl]-N,N-dimethylacrylamide
  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：

  (E)-3-[(S)-5-((tert-butyldimethylsilyloxy)methyl)-1-(3-methoxy-2-nitrobenzoyl)-4,5-dihydro-1H-pyrrol-3-yl]acrylaldehyde 、 二甲胺 在 sodium cyanide 、 manganese(IV) oxide 作用下， 以 四氢呋喃 、 异丙醇 为溶剂， 反应 0.25h， 以64%的产率得到(E)-3-[(S)-5-((tert-butyldimethylsilyloxy)methyl)-1-(3-methoxy-2-nitrobenzoyl)-4,5-dihydro-1H-pyrrol-3-yl]-N,N-dimethylacrylamide
  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.