(4E,7S)-N-{(2R)-[(1R,6R)-6-allyloxy-3-methyl-2-oxocyclohex-3-en-1-yl]-2-methoxyethyl}-7-methoxydodec-4-enamide | 1048014-04-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (4E,7S)-N-{(2R)-[(1R,6R)-6-allyloxy-3-methyl-2-oxocyclohex-3-en-1-yl]-2-methoxyethyl}-7-methoxydodec-4-enamide
• 英文别名: (E,7S)-7-methoxy-N-[(2R)-2-methoxy-2-[(1R,6R)-3-methyl-2-oxo-6-prop-2-enoxycyclohex-3-en-1-yl]ethyl]dodec-4-enamide
• CAS: 1048014-04-5
• 化学式: C₂₆H₄₃NO₅
• 分子量: 449.631
• InChiKey: ZHEKMSFRASGLOI-ZHAFXUNJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  32
• 可旋转键数：
  17
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  73.9
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (4E,7S)-N-{(2R)-[(1R,6R)-6-allyloxy-3-methyl-2-oxocyclohex-3-en-1-yl]-2-methoxyethyl}-7-methoxydodec-4-enamide 在 palladium dichloride 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 3.0h， 以33%的产率得到(4E,7S)-N-{(2R)-[(1R,6R)-6-hydroxy-3-methyl-2-oxocyclohex-3-en-1-yl]-2-methoxyethyl}-7-methoxydodec-4-enamide
  参考文献：
  名称：

  An Improved Asymmetric Synthesis of Malyngamide U and Its 2′-Epimer

  摘要：

  An accelerated and improved asymmetric synthesis of malyngamide U (1) and its 2'-epimer (2'-epi-1) was accomplished from readily available n-hexanal, ethanolamine and (R)-(-)-carvone. The key steps involved a Johnson-Claisen rearrangement in the synthesis of an unsaturated carboxylic acid 4 and an aldol reaction in the construction of the skeleton of I and 2'-epi-1. There are 13 steps in the synthesis, with a 2.7% overall yield for 1 and a 0.4% yield for 2'-epi-1.

  DOI：

  10.1021/jo800876u
• 作为产物：
  描述：

  (4E,7S)-N-{(2R)-[(1S,6R)-6-allyloxy-3-methyl-2-oxocyclohex-3-en-1-yl]-2-hydroxyethyl}-7-methoxydodec-4-enamide 、 碘甲烷 在 calcium sulfate 、 silver(l) oxide 作用下， 反应 24.0h， 以71%的产率得到(4E,7S)-N-{(2R)-[(1R,6R)-6-allyloxy-3-methyl-2-oxocyclohex-3-en-1-yl]-2-methoxyethyl}-7-methoxydodec-4-enamide
  参考文献：
  名称：

  An Improved Asymmetric Synthesis of Malyngamide U and Its 2′-Epimer

  摘要：

  An accelerated and improved asymmetric synthesis of malyngamide U (1) and its 2'-epimer (2'-epi-1) was accomplished from readily available n-hexanal, ethanolamine and (R)-(-)-carvone. The key steps involved a Johnson-Claisen rearrangement in the synthesis of an unsaturated carboxylic acid 4 and an aldol reaction in the construction of the skeleton of I and 2'-epi-1. There are 13 steps in the synthesis, with a 2.7% overall yield for 1 and a 0.4% yield for 2'-epi-1.

  DOI：

  10.1021/jo800876u