methyl (5Z,8Z,11Z,14Z)-17,17-diethoxyheptadeca-5,8,11,14-tetraenoate | 208983-31-7

• 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: methyl (5Z,8Z,11Z,14Z)-17,17-diethoxyheptadeca-5,8,11,14-tetraenoate
• CAS: 208983-31-7
• 化学式: C₂₂H₃₆O₄
• 分子量: 364.525
• InChiKey: JLPKGAFJXFBHIC-RYSLWBTDSA-N

物化性质

• 沸点：
  435.804±45.00 °C(Press: 760.00 Torr)(predicted)
• 密度：
  0.952±0.06 g/cm3(Temp: 25 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  26
• 可旋转键数：
  17
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  methyl (5Z,8Z,11Z,14Z)-17,17-diethoxyheptadeca-5,8,11,14-tetraenoate 在 正丁基锂 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 3.5h， 生成 二十碳五烯酸甲酯
  参考文献：
  名称：

  Synthesis of methyl (5Z,8Z,11Z,14Z,17Z)- and (5Z,8Z,11Z,14Z,17E)-[18-14C] eicosapentaenoate

  摘要：

  In order to have a better insight of the effect of the double bond geometry of EPA on its anti-aggregating properties, methyl ester of [18-C-14] EPA and of its Delta 17t isomer were synthesized from a common intermediate [(3Z,6Z,9Z)-12,12-diethoxydodeca-3,6,9-trienyl]triphenylphosphonium iodide 11 via three sequential Wittig olelination. Labelled methyl ester of EPA 16b and EPA Delta 17t 17b were obtained in near 100% isomeric and radiochemical purities.

  DOI：

  10.1002/(sici)1099-1344(199805)41:5<411::aid-jlcr94>3.0.co;2-7
• 作为产物：
  描述：

  4,4-diethoxybut-1-yne 在 Lindlar's catalyst 咪唑 、 喹啉 、 正丁基锂 、 三氟化硼乙醚 、 四丁基氟化铵 、 氢气 、 碘 、 三苯基膦 、 calcium carbonate 作用下， 以 四氢呋喃 、 正己烷 、 乙腈 为溶剂， 反应 151.08h， 生成 methyl (5Z,8Z,11Z,14Z)-17,17-diethoxyheptadeca-5,8,11,14-tetraenoate
  参考文献：
  名称：

  Synthesis of methyl (5Z,8Z,11Z,14Z,17Z)- and (5Z,8Z,11Z,14Z,17E)-[18-14C] eicosapentaenoate

  摘要：

  In order to have a better insight of the effect of the double bond geometry of EPA on its anti-aggregating properties, methyl ester of [18-C-14] EPA and of its Delta 17t isomer were synthesized from a common intermediate [(3Z,6Z,9Z)-12,12-diethoxydodeca-3,6,9-trienyl]triphenylphosphonium iodide 11 via three sequential Wittig olelination. Labelled methyl ester of EPA 16b and EPA Delta 17t 17b were obtained in near 100% isomeric and radiochemical purities.

  DOI：

  10.1002/(sici)1099-1344(199805)41:5<411::aid-jlcr94>3.0.co;2-7

文献信息

• Synthesis of methyl (5Z,8Z,11Z,14Z,17Z)- and (5Z,8Z,11Z,14Z,17E)-[18-14C] eicosapentaenoate
  作者：Thierry Eynard、Didier Poullain、Jean-Michel Vatèle、Jean-Pierre Noël、Jean-Michel Chardigny、Jean-Louis Sébédio

  DOI：10.1002/(sici)1099-1344(199805)41:5<411::aid-jlcr94>3.0.co;2-7

  日期：1998.5

  In order to have a better insight of the effect of the double bond geometry of EPA on its anti-aggregating properties, methyl ester of [18-C-14] EPA and of its Delta 17t isomer were synthesized from a common intermediate [(3Z,6Z,9Z)-12,12-diethoxydodeca-3,6,9-trienyl]triphenylphosphonium iodide 11 via three sequential Wittig olelination. Labelled methyl ester of EPA 16b and EPA Delta 17t 17b were obtained in near 100% isomeric and radiochemical purities.