(4S,1'Z,4'Z)-2,2-dimethyl-4-(hepta-1,4-dien-1-yl)-1,3-dioxolane | 460077-76-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (4S,1'Z,4'Z)-2,2-dimethyl-4-(hepta-1,4-dien-1-yl)-1,3-dioxolane
• 英文别名: (4S)-4-[(1Z,4Z)-hepta-1,4-dienyl]-2,2-dimethyl-1,3-dioxolane
• CAS: 460077-76-3
• 化学式: C₁₂H₂₀O₂
• 分子量: 196.29
• InChiKey: JCYBAGKKPUCHPN-KWZSHNQISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (4S,1'Z,4'Z)-2,2-dimethyl-4-(hepta-1,4-dien-1-yl)-1,3-dioxolane 在 盐酸 、 六甲基磷酰三胺 、 4-二甲氨基吡啶 、 lithium hydroxide 、 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 47.83h， 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
• 作为产物：
  描述：

  (3Z)-3-hexenyltriphenylphosphonium bromide 、 (R)-(+)-2,2-二甲基-1,3-二氧戊环-4-甲醛 在 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 为溶剂， 反应 4.0h， 以69%的产率得到(4S,1'Z,4'Z)-2,2-dimethyl-4-(hepta-1,4-dien-1-yl)-1,3-dioxolane
  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.