4,7,10,13-hexadecatetraen-1-yn | 1001846-21-4

• 分子结构分类: 有机化合物 - 碳氢化合物 - 不饱和烃
• 英文名称: 4,7,10,13-hexadecatetraen-1-yn
• 英文别名: (4Z,7Z,10Z,13Z)-hexadeca-4,7,10,13-tetraen-1-yne
• CAS: 1001846-21-4
• 化学式: C₁₆H₂₂
• 分子量: 214.351
• InChiKey: HJQJVWATGSIGHN-YEMTZORJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  16
• 可旋转键数：
  8
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  4,7,10,13-hexadecatetraen-1-yn 在 正丁基锂 、 sulfur 作用下， 以 乙醚 为溶剂， 反应 1.5h， 生成
  参考文献：
  名称：

  Syntheses of Some Sulfur‐Containing Polyunsaturated Fatty Acids as Potential Lipoxygenase Inhibitors

  摘要：

  Starting from (all-Z)-eicosa-5,8,11,14,17-pentaenoic acid (EPA) and (all-Z)-4,7,10,13,16,19-docosahexaenoic acid (DHA), several polyunsaturated fatty acids, containing a sulfur atom either in the chain or in a thiophene ring, have been synthesized as potential inhibitors of lipoxygenases.

  DOI：

  10.1080/00397910701575053
• 作为产物：
  描述：

  all-(Z)-3,6,9,12-pentadecatetraenal 在 甲基锂 、 三苯基膦 、 锌 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 43.0h， 生成 4,7,10,13-hexadecatetraen-1-yn
  参考文献：
  名称：

  Stereoselective synthesis of zooxanthellactone

  摘要：

  The marine polyunsaturated natural product zooxanthellactone was synthesized in six steps and in 11% overall yield from eicosapentaenoic acid. The key synthetic steps were a Sonogashira cross-coupling reaction and a stereoselective semi-reduction. These efforts, together with NMR and optical rotation data, confirmed the reported structure of zooxanthellactone. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2014.03.085

文献信息

• Stereoselective synthesis of (all-Z)-hentriaconta-3,6,9,12,15,19,22,25,28-nonaene
  作者：Liudmila Filippova、Ida Aarum、Martine Ringdal、Martin Kirkhus Dahl、Trond Vidar Hansen、Yngve Stenstrøm

  DOI：10.1039/c5ob00313j

  日期：——

  EPA-EE was converted in eight steps and 15% overall yield to the natural product (all-Z)-hentriaconta-3,6,9,12,15,19,22,25,28-nonaene. The synthesis confirms the all-Z-configuration of all nine double bonds.

  EPA-EE经过八个步骤的转化，总产率为15％，得到了天然产物（全Z）-hentriaconta-3,6,9,12,15,19,22,25,28-nonaene。该合成证实了所有九个双键的全Z构型。
• Syntheses of Some Sulfur‐Containing Polyunsaturated Fatty Acids as Potential Lipoxygenase Inhibitors
  作者：Solveig Flock、Anne Kristin Holmeide、Lars Skattebøl

  DOI：10.1080/00397910701575053

  日期：2007.11

  Starting from (all-Z)-eicosa-5,8,11,14,17-pentaenoic acid (EPA) and (all-Z)-4,7,10,13,16,19-docosahexaenoic acid (DHA), several polyunsaturated fatty acids, containing a sulfur atom either in the chain or in a thiophene ring, have been synthesized as potential inhibitors of lipoxygenases.
• Stereoselective synthesis of zooxanthellactone
  作者：Martin Gjerde Jakobsen、Anders Vik、Trond Vidar Hansen

  DOI：10.1016/j.tetlet.2014.03.085

  日期：2014.4

  The marine polyunsaturated natural product zooxanthellactone was synthesized in six steps and in 11% overall yield from eicosapentaenoic acid. The key synthetic steps were a Sonogashira cross-coupling reaction and a stereoselective semi-reduction. These efforts, together with NMR and optical rotation data, confirmed the reported structure of zooxanthellactone. (C) 2014 Elsevier Ltd. All rights reserved.