methyl (17S)-17-hydroxyoctadeca-9,12,15-triynoate | 530099-04-8

• 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 (17S)-17-hydroxyoctadeca-9,12,15-triynoate
• CAS: 530099-04-8
• 化学式: C₁₉H₂₆O₃
• 分子量: 302.414
• InChiKey: ALPRKHGMMBKQPB-SFHVURJKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  22
• 可旋转键数：
  8
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.63
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  methyl (17S)-17-hydroxyoctadeca-9,12,15-triynoate 在 P₂-Ni 氢气 作用下， 以 乙醇 为溶剂， 反应 6.0h， 以90%的产率得到(S)-17-hydroxylinolenic acid methyl ester
  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 正丁基锂 、 三甲基氯硅烷 、 乙基溴化镁 、 三溴化磷 、 potassium iodide 、 copper(l) chloride 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 30.0h， 生成 methyl (17S)-17-hydroxyoctadeca-9,12,15-triynoate
  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.