ethyl (4E,7S)-7-methoxydodec-4-enoate | 1048013-43-9

• 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: ethyl (4E,7S)-7-methoxydodec-4-enoate
• 英文别名: ethyl (E,7S)-7-methoxydodec-4-enoate
• CAS: 1048013-43-9
• 化学式: C₁₅H₂₈O₃
• 分子量: 256.386
• InChiKey: XECRYZWZAFKWRG-KGXGESDWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  18
• 可旋转键数：
  12
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  ethyl (4E,7S)-7-methoxydodec-4-enoate 在 氢氧化钾 作用下， 以 乙醇 、 水 为溶剂， 反应 1.0h， 以93%的产率得到(-)-(4E,7S)-7-methoxydodec-4-enoic acid
  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：

  (5S)-5-methoxydec-1-en-3-ol 、 原乙酸三乙酯 在 丙酸 作用下， 以 甲苯 为溶剂， 反应 1.0h， 以89%的产率得到ethyl (4E,7S)-7-methoxydodec-4-enoate
  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.