(9Z,12Z,15Z,17S)-17-hydroxyoctadeca-9,12,15-trienoic acid | 307524-17-0

• 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: (9Z,12Z,15Z,17S)-17-hydroxyoctadeca-9,12,15-trienoic acid
• CAS: 307524-17-0
• 化学式: C₁₈H₃₀O₃
• 分子量: 294.434
• InChiKey: PSQSSLVXOIJSMX-RZABLGLBSA-N

物化性质

• 沸点：
  429.3±33.0 °C(Predicted)
• 密度：
  0.984±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  21
• 可旋转键数：
  13
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.61
• 拓扑面积：
  57.5
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  L-谷氨酰胺 、 (9Z,12Z,15Z,17S)-17-hydroxyoctadeca-9,12,15-trienoic acid 在 氯甲酸乙酯 、 三乙胺 、 sodium hydroxide 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 0.75h， 以82%的产率得到N-(17S)-17-hydroxylinonolenoyl-L-glutamine
  参考文献：
  名称：

  Synthesis of hydroxy-substituted unsaturated fatty acids and the amino-acid insect-derivative volicitin

  摘要：

  An efficient synthesis of N-(17S-hydroxylinolenOyl)-L-glutamine (volicitin), a chemical elicitor from the herbivore-pest beet armyworm is presented. The synthesis, which utilizes a copper-catalyzed acetylene coupling, links (S)-3,6-heptadiyne-2-ol with a C-8 propargylic iodine methyl ester to form the (S)-17-hydroxylinolenate skeleton. By substituting different heptadiyne-2-ol groups, a series of methylene interrupted polyacetylene analogues were generated. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(02)02640-0
• 作为产物：
  描述：

  8-溴辛酸 在 P₂-Ni lithium hydroxide 、 正丁基锂 、 三甲基氯硅烷 、 乙基溴化镁 、 氢气 、 三溴化磷 、 potassium iodide 、 copper(l) chloride 作用下， 以 四氢呋喃 、 乙醇 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 48.0h， 生成 (9Z,12Z,15Z,17S)-17-hydroxyoctadeca-9,12,15-trienoic acid
  参考文献：
  名称：

  Synthesis of hydroxy-substituted unsaturated fatty acids and the amino-acid insect-derivative volicitin

  摘要：

  An efficient synthesis of N-(17S-hydroxylinolenOyl)-L-glutamine (volicitin), a chemical elicitor from the herbivore-pest beet armyworm is presented. The synthesis, which utilizes a copper-catalyzed acetylene coupling, links (S)-3,6-heptadiyne-2-ol with a C-8 propargylic iodine methyl ester to form the (S)-17-hydroxylinolenate skeleton. By substituting different heptadiyne-2-ol groups, a series of methylene interrupted polyacetylene analogues were generated. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(02)02640-0

文献信息

• Synthesis of hydroxy-substituted unsaturated fatty acids and the amino-acid insect-derivative volicitin
  作者：Han-Xun Wei、Christopher L. Truitt、Paul W. Paré

  DOI：10.1016/s0040-4039(02)02640-0

  日期：2003.1

  An efficient synthesis of N-(17S-hydroxylinolenOyl)-L-glutamine (volicitin), a chemical elicitor from the herbivore-pest beet armyworm is presented. The synthesis, which utilizes a copper-catalyzed acetylene coupling, links (S)-3,6-heptadiyne-2-ol with a C-8 propargylic iodine methyl ester to form the (S)-17-hydroxylinolenate skeleton. By substituting different heptadiyne-2-ol groups, a series of methylene interrupted polyacetylene analogues were generated. (C) 2003 Elsevier Science Ltd. All rights reserved.