(E,7S)-7-methoxy-N-(2-oxoethyl)dodec-4-enamide | 1048013-33-7

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (E,7S)-7-methoxy-N-(2-oxoethyl)dodec-4-enamide
• CAS: 1048013-33-7
• 化学式: C₁₅H₂₇NO₃
• 分子量: 269.384
• InChiKey: PMVYVKRIJOBQCK-DYLGSBMWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  19
• 可旋转键数：
  12
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  55.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (R)-5-allyloxy-2-methylcyclohex-2-enone 、 (E,7S)-7-methoxy-N-(2-oxoethyl)dodec-4-enamide 、 碘甲烷 在 lithium diisopropyl amide 、 calcium sulfate 、 silver(l) oxide 作用下， 以 四氢呋喃 为溶剂， 反应 25.25h， 以41 mg的产率得到(4E,7S)-N-{(2S)-[(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
• 作为产物：
  描述：

  (4E,7S)-N-(2-hydroxyethyl)-7-methoxydodec-4-enamide 在 2-碘酰基苯甲酸 作用下， 以 乙酸乙酯 为溶剂， 反应 7.0h， 生成 (E,7S)-7-methoxy-N-(2-oxoethyl)dodec-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

文献信息

• An Improved Asymmetric Synthesis of Malyngamide U and Its 2′-Epimer
  作者：Jian-Peng Feng、Zi-Fa Shi、Yang Li、Jun-Tao Zhang、Xian-Liang Qi、Jie Chen、Xiao-Ping Cao

  DOI：10.1021/jo800876u

  日期：2008.9.1

  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.