(11S,9Z)-11,12-dihydroxydodec-9-enoic acid methyl ester | 460077-83-2

• 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: (11S,9Z)-11,12-dihydroxydodec-9-enoic acid methyl ester
• 英文别名: methyl (Z,11S)-11,12-dihydroxydodec-9-enoate
• CAS: 460077-83-2
• 化学式: C₁₃H₂₄O₄
• 分子量: 244.331
• InChiKey: BZRHVBXFOUFZOT-UPZNUWHASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  17
• 可旋转键数：
  11
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.77
• 拓扑面积：
  66.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (11S,9Z)-11,12-dihydroxydodec-9-enoic acid methyl ester 在 4-二甲氨基吡啶 、 四丁基氟化铵 、 sodium acetate 、 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 、 pyridinium chlorochromate 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 为溶剂， 反应 60.25h， 生成 (11S,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
• 作为产物：
  描述：

  (9-methoxy-9-oxononyl)triphenylphosphonium bromide 在 盐酸 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 甲醇 、 水 为溶剂， 反应 6.75h， 生成 (11S,9Z)-11,12-dihydroxydodec-9-enoic 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

• 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.