N-((4S,5S,6S,E)-6-hydroxy-2-methyl-8-phenyl-5-(pyrrolidin-1-yl)oct-7-en-4-yl)-4-nitrobenzamide | 1452492-31-7

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂醇
• 英文名称: N-((4S,5S,6S,E)-6-hydroxy-2-methyl-8-phenyl-5-(pyrrolidin-1-yl)oct-7-en-4-yl)-4-nitrobenzamide
• 英文别名: N-[(E,4S,5S,6S)-6-hydroxy-2-methyl-8-phenyl-5-pyrrolidin-1-yloct-7-en-4-yl]-4-nitrobenzamide
• CAS: 1452492-31-7
• 化学式: C₂₆H₃₃N₃O₄
• 分子量: 451.566
• InChiKey: HGVSPNQPCKWKRF-KTLLCTQTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  33
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  98.4
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  反式-BETA-苯乙烯硼酸 在 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 28.0h， 生成 N-((4S,5S,6S,E)-6-hydroxy-2-methyl-8-phenyl-5-(pyrrolidin-1-yl)oct-7-en-4-yl)-4-nitrobenzamide
  参考文献：
  名称：

  Stereocontrolled Synthesis of 1,2- and 1,3-Diamine Building Blocks from Aziridine Aldehyde Dimers

  摘要：

  Vicinal aziridine-containing diamines have been obtained with high syn-stereoselectivity from readily available aziridine aldehyde dimers in the Petasis borono-Mannich reaction. Subsequent solvent- and/or nucleophile-dependent ring-opening of the aziridine ring yields functionalized 1,2- and 1,3-diamines with high regioselectivity. The ring opening is also influenced by the substitution at the C3 position of the aziridine. A mechanistic rationale for the highly syn-selective three-component reaction is proposed.

  DOI：

  10.1021/jo401489q

文献信息

• Stereocontrolled Synthesis of 1,2- and 1,3-Diamine Building Blocks from Aziridine Aldehyde Dimers
  作者：Sean K. Liew、Zhi He、Jeffrey D. St. Denis、Andrei K. Yudin

  DOI：10.1021/jo401489q

  日期：2013.12.6

  Vicinal aziridine-containing diamines have been obtained with high syn-stereoselectivity from readily available aziridine aldehyde dimers in the Petasis borono-Mannich reaction. Subsequent solvent- and/or nucleophile-dependent ring-opening of the aziridine ring yields functionalized 1,2- and 1,3-diamines with high regioselectivity. The ring opening is also influenced by the substitution at the C3 position of the aziridine. A mechanistic rationale for the highly syn-selective three-component reaction is proposed.