(11R,9Z,12Z,15Z)-11-hydroxyoctadeca-9,12,15-trienoic acid methyl ester | 290349-14-3

• 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: (11R,9Z,12Z,15Z)-11-hydroxyoctadeca-9,12,15-trienoic acid methyl ester
• 英文别名: (11R)-hydroxyoctadeca-9(Z),12(Z),15(Z)-trienoic acid methyl ester；methyl (9Z,11R,12Z,15Z)-11-hydroxyoctadeca-9,12,15-trienoate
• CAS: 290349-14-3
• 化学式: C₁₉H₃₂O₃
• 分子量: 308.461
• InChiKey: YKJRPZGHGROFSP-IWDOAGBQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  22
• 可旋转键数：
  14
• 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：

  (11R,9Z,12Z,15Z)-11-hydroxyoctadeca-9,12,15-trienoic acid methyl ester 在 lithium hydroxide 作用下， 以 甲醇 为溶剂， 反应 3.5h， 以95%的产率得到(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
• 作为产物：
  描述：

  (3Z)-3-hexenyltriphenylphosphonium bromide 在 盐酸 、 六甲基磷酰三胺 、 4-二甲氨基吡啶 、 四丙基高钌酸铵 、 2-methylmorpholine N-oxide 、 乙醇 、 4 A molecular sieve 、 四丁基氟化铵 、 4-甲基苯磺酸吡啶 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 三乙胺 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 水 为溶剂， 反应 48.33h， 生成 (11R,9Z,12Z,15Z)-11-hydroxyoctadeca-9,12,15-trienoic acid methyl ester
  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

• Chiral Silylation Reagents for the Determination of Absolute Configuration by NMR Spectroscopy
  作者：Douglas B. Weibel、Tameka R. Walker、Frank C. Schroeder、Jerrold Meinwald

  DOI：10.1021/ol006162h

  日期：2000.7.1

  We have investigated the use of chiral silylating reagents as analytical probes for determining the absolute stereochemistry of natural products by NMR spectroscopy. These reagents are prepared in high chemical yield in one step and can be used to derivatize chiral allylic alcohols which are incompatible with ester-based methodologies. Microscale ( approximately 400 nmol) derivatization conditions

  我们已经研究了使用手性甲硅烷基化试剂作为分析探针通过NMR光谱法测定天然产物的绝对立体化学的方法。这些试剂可一步一步以高化学产率制备，可用于衍生与基于酯的方法不相容的手性烯丙基醇。已经定义了微型（约400 nmol）衍生条件。所得的硅氧烷非对映异构体容易通过它们的（1）H NMR谱来区分。
• 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.