(S)-5-((1E,6Z,9Z,12Z,15Z)-octadeca-1,6,9,12,15-pentaen-3-yn-1-yl)dihydrofuran-2(3H)-one | 1607478-69-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 英文名称: (S)-5-((1E,6Z,9Z,12Z,15Z)-octadeca-1,6,9,12,15-pentaen-3-yn-1-yl)dihydrofuran-2(3H)-one
• 英文别名: (5S)-5-[(1E,6Z,9Z,12Z,15Z)-octadeca-1,6,9,12,15-pentaen-3-ynyl]oxolan-2-one
• CAS: 1607478-69-2
• 化学式: C₂₂H₂₈O₂
• 分子量: 324.463
• InChiKey: GMROLOSGDIBMAQ-XNRRGOMCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  24
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (S)-5-((1E,6Z,9Z,12Z,15Z)-octadeca-1,6,9,12,15-pentaen-3-yn-1-yl)dihydrofuran-2(3H)-one 在 吡啶 、 5% palladium on barium sulphate 、 氢气 作用下， 反应 4.5h， 以29%的产率得到zooxanthellactone
  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
• 作为产物：
  描述：

  (S)-(+)-5-氧代-2-四氢呋喃羧酸 在 chromium dichloride 、 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 草酰氯 、 碘仿 、 rosenmund catalyst 、 氢气 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 甲苯 为溶剂， 反应 22.5h， 生成 (S)-5-((1E,6Z,9Z,12Z,15Z)-octadeca-1,6,9,12,15-pentaen-3-yn-1-yl)dihydrofuran-2(3H)-one
  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 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.