(4Z,7Z,10Z,13Z)-hexadeca-4,7,10,13-tetraenal | 309728-58-3

• 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: (4Z,7Z,10Z,13Z)-hexadeca-4,7,10,13-tetraenal
• CAS: 309728-58-3
• 化学式: C₁₆H₂₄O
• 分子量: 232.366
• InChiKey: MCJZAFLSUPAMEV-LTKCOYKYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  17
• 可旋转键数：
  10
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (4Z,7Z,10Z,13Z)-hexadeca-4,7,10,13-tetraenal 在 六甲基磷酰三胺 、 copper(l) iodide 、 二异丁基氢化铝 、 potassium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 正己烷 、 二氯甲烷 、 水 为溶剂， 反应 8.5h， 生成 顺6,9,12,15-十八碳四烯酸
  参考文献：
  名称：

  Concise syntheses of three ω-3 polyunsaturated fatty acids

  摘要：

  The synthesis of the three omega-3 polyunsaturated fatty acids, eicosatetraenoic acid (3), docosapentaenoic acid (4), and stearidonic acid (5) has been achieved using eicosapentaenoic acid or docosahexaenoic acid as the starting materials. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2012.08.009
• 作为产物：
  描述：

  全顺式二十碳五烯酸 在 正丁基锂 、 碘 、 potassium hydrogencarbonate 、 高碘酸 、 potassium iodide 作用下， 以 四氢呋喃 、 甲醇 、 正己烷 、 水 为溶剂， 反应 2.5h， 生成 (4Z,7Z,10Z,13Z)-hexadeca-4,7,10,13-tetraenal
  参考文献：
  名称：

  Concise syntheses of three ω-3 polyunsaturated fatty acids

  摘要：

  The synthesis of the three omega-3 polyunsaturated fatty acids, eicosatetraenoic acid (3), docosapentaenoic acid (4), and stearidonic acid (5) has been achieved using eicosapentaenoic acid or docosahexaenoic acid as the starting materials. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2012.08.009

文献信息

• Synthesis of obscuraminol A using an organocatalyzed enantioselective Henry reaction
  作者：Liudmila Filippova、Simen Antonsen、Yngve Stenstrøm、Trond Vidar Hansen

  DOI：10.1016/j.tet.2016.08.070

  日期：2016.10

  The first synthesis of the polyunsaturated amino alcohol natural product obscuraminol A is reported. This stereoselective synthesis was based on an anti- and enantioselective organocatalyzed Henry reaction followed by a chemoselective SmI2-mediated reduction that affected only the nitro-group of the Henry product. These efforts yielded obscuraminol A where the configuration of the all-Z skipped double

  报道了多不饱和氨基醇天然产物黑松香A的首次合成。该立体选择性合成是基于抗和对映选择性的有机催化的亨利反应，然后进行化学选择性的SmI 2介导的还原，该还原仅影响亨利产物的硝基。这些努力产生了obscuraminol A，其中从起始原料（即）保守了全Z跳过的双键的构型。（全-Z）-二十碳五，8、11、14、17-戊烯酸的乙酯。我们的合成证实了已报道的黑松香醇A的结构。
• Syntheses of three metabolites of icosapentaenoic and docosahexaenoic acids
  作者：Solveig Flock、Lars Skattebøl

  DOI：10.1039/b004101g

  日期：——

  Starting from the n − 3 polyunsaturated fatty acids icosapentaenoic acid (1, EPA) and docosahexaenoic acid (2, DHA), the syntheses of methyl 2E,4Z,8Z,11Z,14Z,17Z-icosa-2,4,8,11,14,17-hexaenoate (6), 2E,8Z,11Z,14Z,17Z-icosa-2,8,11,14,17-pentaenoate (7) and 2E,4Z,7Z,10Z,13Z,16Z,19Z-docosa-2,4,7,10,13,16,19-heptaenoate (8), in high stereochemical purity, have been accomplished. The corresponding carboxylic acids have been reported as metabolites in the bioconversion of EPA and DHA.

  17-六烯酸甲酯（6）、2E,8Z,11Z,14Z,17Z-二十二碳-2,8,11,14,17-五烯酸甲酯（7）和 2E,4Z,7Z,10Z,13Z,16Z,19Z-二十二碳-2,4,7,10,13,16,19-庚烯酸甲酯（8）的高立体化学纯度合成。据报道，相应的羧酸是 EPA 和 DHA 生物转化过程中的代谢产物。
• Synthesis of All-Z-1,6,9,12,15-Octadecapenten-3-one, A Vinyl Ketone Polyunsaturated Marine Natural Product Isolated from Callysponga sp.
  作者：Anne Langseter、Yngve Stenstrøm、Lars Skattebøl

  DOI：10.3390/molecules19033804

  日期：——

  The synthesis of the marine natural product 1,6Z,9Z,12Z,15Z-octadecapentaen-3-one (1) has been achieved by two different routes starting from the ethyl esters of eicosapentaenoic acid (EPA) and docosahexaenoic acid (DHA), respectively. Using EPA ethyl ester as starting material the polyunsaturated vinyl ketone lipid 1 was obtained in 17% overall yield.

  海洋天然产物 1,6Z,9Z,12Z,15Z-octadecapentaen-3-one (1) 的合成是通过两种不同的路线从二十碳五烯酸 (EPA) 和二十二碳六烯酸 (DHA) 乙酯开始合成的，分别。使用EPA乙酯作为起始原料，以17%的总产率获得多不饱和乙烯基酮脂质1。
• 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。
• Concise syntheses of three ω-3 polyunsaturated fatty acids
  作者：Martin Gjerde Jakobsen、Anders Vik、Trond Vidar Hansen

  DOI：10.1016/j.tetlet.2012.08.009

  日期：2012.10

  The synthesis of the three omega-3 polyunsaturated fatty acids, eicosatetraenoic acid (3), docosapentaenoic acid (4), and stearidonic acid (5) has been achieved using eicosapentaenoic acid or docosahexaenoic acid as the starting materials. (C) 2012 Elsevier Ltd. All rights reserved.