(2S,3S,5R)-3-acetyl-2-benzyl-1-(ethoxycarbonyl)-5-nonylpyrrolidine | 159154-01-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 英文名称: (2S,3S,5R)-3-acetyl-2-benzyl-1-(ethoxycarbonyl)-5-nonylpyrrolidine
• 英文别名: ethyl (2S,3S,5R)-3-acetyl-2-benzyl-5-nonylpyrrolidine-1-carboxylate
• CAS: 159154-01-5
• 化学式: C₂₅H₃₉NO₃
• 分子量: 401.59
• InChiKey: ZWCJKGGANIRQMD-SMIHKQSGSA-N

物化性质

• 沸点：
  506.0±43.0 °C(Predicted)
• 密度：
  1.012±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.9
• 重原子数：
  29
• 可旋转键数：
  13
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.68
• 拓扑面积：
  46.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (2S,3S,5R)-3-acetyl-2-benzyl-1-(ethoxycarbonyl)-5-nonylpyrrolidine 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 丙酮 为溶剂， 反应 2.0h， 生成 (2S,3R,5R)-3-acetyl-2-benzyl-1-(ethoxycarbonyl)-5-nonylpyrrolidine
  参考文献：
  名称：

  Enantioselective Total Synthesis of Either Enantiomer of the Antifungal Antibiotic Preussin (L-657,398) from (S)-Phenylalanine

  摘要：

  Enantioselective total syntheses of the antifungal agent (+)-preussin (1) and its enantiomer (-)-1 from (S)-phenylalanine are described. The central transformations are protic acid-promoted aza-Cope rearrangement-Mannich cyclization reactions (12 --> 19 and 13 --> 27, Schemes 4 and 6). Retro-Mannich fragmentation-Mannich cyclization (27 --> 28, Scheme 6) is key to the formation of (-)-1. This study demonstrates, for the first time, that enantioenriched substituted pyrrolidines can be prepared using the aza-Cope-Mannich rearrangement.

  DOI：

  10.1021/ja00104a005
• 作为产物：
  描述：

  (4S,5S)-4-benzyl-5-ethenyl-5-methyl-2-nonyl-1,3-oxazolidine 在 2,2,2-三氟乙醇 、 camphor-10-sulfonic acid 、 碳酸氢钠 作用下， 反应 42.0h， 生成 (2S,3S,5R)-3-acetyl-2-benzyl-1-(ethoxycarbonyl)-5-nonylpyrrolidine
  参考文献：
  名称：

  Enantioselective Total Synthesis of Either Enantiomer of the Antifungal Antibiotic Preussin (L-657,398) from (S)-Phenylalanine

  摘要：

  Enantioselective total syntheses of the antifungal agent (+)-preussin (1) and its enantiomer (-)-1 from (S)-phenylalanine are described. The central transformations are protic acid-promoted aza-Cope rearrangement-Mannich cyclization reactions (12 --> 19 and 13 --> 27, Schemes 4 and 6). Retro-Mannich fragmentation-Mannich cyclization (27 --> 28, Scheme 6) is key to the formation of (-)-1. This study demonstrates, for the first time, that enantioenriched substituted pyrrolidines can be prepared using the aza-Cope-Mannich rearrangement.

  DOI：

  10.1021/ja00104a005

文献信息

• Enantioselective Total Synthesis of Either Enantiomer of the Antifungal Antibiotic Preussin (L-657,398) from (S)-Phenylalanine
  作者：Wei Deng、Larry E. Overman

  DOI：10.1021/ja00104a005

  日期：1994.12

  Enantioselective total syntheses of the antifungal agent (+)-preussin (1) and its enantiomer (-)-1 from (S)-phenylalanine are described. The central transformations are protic acid-promoted aza-Cope rearrangement-Mannich cyclization reactions (12 --> 19 and 13 --> 27, Schemes 4 and 6). Retro-Mannich fragmentation-Mannich cyclization (27 --> 28, Scheme 6) is key to the formation of (-)-1. This study demonstrates, for the first time, that enantioenriched substituted pyrrolidines can be prepared using the aza-Cope-Mannich rearrangement.