(11R,9Z,12Z,15Z)-11-hydroxyoctadeca-9,12,15-trienoic acid | 443971-28-6

• 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: (11R,9Z,12Z,15Z)-11-hydroxyoctadeca-9,12,15-trienoic acid
• 英文别名: (11R)-hydroxylinolenic acid；(9Z,11R,12Z,15Z)-11-hydroxyoctadeca-9,12,15-trienoic acid
• CAS: 443971-28-6
• 化学式: C₁₈H₃₀O₃
• 分子量: 294.434
• InChiKey: JMYBEIGSPWECBU-JZTOSSBESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 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：

  棕榈酸 、 (11R,9Z,12Z,15Z)-11-hydroxyoctadeca-9,12,15-trienoic acid 在 4-二甲氨基吡啶 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 22.0h， 以59%的产率得到(11S,9Z,12Z,15Z)-11-hexadecanoyloxyoctadeca-9,12,15-trienoic acid
  参考文献：
  名称：

  Synthesis of Mayolene-16 and Mayolene-18:  Larval Defensive Lipids from the European Cabbage Butterfly

  摘要：

  A tandem Wittig approach has been employed for the synthesis of both (11S,9Z,l2Z,15Z)- and (11R,9Z,12Z,15Z)-hydroxyoctadeca-9,12,15-trienoic acid (11-hydroxylinolenic acid, 11-HLA) from (R)-glyceraldehyde acetonide. From (11R)-HIA we have prepared the corresponding palmitic acid and stearic acid esters, mayolene-16 (1) and mayolene-18 (2), insect defensive compounds recently identified from Pieris rapae larvae. In addition, we describe the synthesis of three macrocyclic oligomers (24-26) derived from (11R)-HLA.

  DOI：

  10.1021/jo011102q
• 作为产物：
  描述：

  (11R,9Z,12Z,15Z)-11-[(tert-butyldiphenylsilyl)oxy]octadeca-9,12,15-trienoic acid methyl ester 在 lithium hydroxide 、 四丁基氟化铵 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 8.0h， 生成 (11R,9Z,12Z,15Z)-11-hydroxyoctadeca-9,12,15-trienoic acid
  参考文献：
  名称：

  Synthesis of Mayolene-16 and Mayolene-18:  Larval Defensive Lipids from the European Cabbage Butterfly

  摘要：

  A tandem Wittig approach has been employed for the synthesis of both (11S,9Z,l2Z,15Z)- and (11R,9Z,12Z,15Z)-hydroxyoctadeca-9,12,15-trienoic acid (11-hydroxylinolenic acid, 11-HLA) from (R)-glyceraldehyde acetonide. From (11R)-HIA we have prepared the corresponding palmitic acid and stearic acid esters, mayolene-16 (1) and mayolene-18 (2), insect defensive compounds recently identified from Pieris rapae larvae. In addition, we describe the synthesis of three macrocyclic oligomers (24-26) derived from (11R)-HLA.

  DOI：

  10.1021/jo011102q

文献信息

• Synthesis of Mayolene-16 and Mayolene-18:  Larval Defensive Lipids from the European Cabbage Butterfly
  作者：Douglas B. Weibel、Laura E. Shevy、Frank C. Schroeder、Jerrold Meinwald

  DOI：10.1021/jo011102q

  日期：2002.8.1

  A tandem Wittig approach has been employed for the synthesis of both (11S,9Z,l2Z,15Z)- and (11R,9Z,12Z,15Z)-hydroxyoctadeca-9,12,15-trienoic acid (11-hydroxylinolenic acid, 11-HLA) from (R)-glyceraldehyde acetonide. From (11R)-HIA we have prepared the corresponding palmitic acid and stearic acid esters, mayolene-16 (1) and mayolene-18 (2), insect defensive compounds recently identified from Pieris rapae larvae. In addition, we describe the synthesis of three macrocyclic oligomers (24-26) derived from (11R)-HLA.