(E,E)-4,8-Dimethyl-10-(tetrahydropyran-2'-yloxy)-3,8-decadienecarboxylic acid | 111351-05-4

• 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: (E,E)-4,8-Dimethyl-10-(tetrahydropyran-2'-yloxy)-3,8-decadienecarboxylic acid
• 英文别名: (3E,8E)-4,8-dimethyl-10-(oxan-2-yloxy)deca-3,8-dienoic acid
• CAS: 111351-05-4
• 化学式: C₁₇H₂₈O₄
• 分子量: 296.407
• InChiKey: FMLCBAHKUFEIAP-YFVJMOTDSA-N

物化性质

• 沸点：
  452.4±45.0 °C(Predicted)
• 密度：
  1.04±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  21
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (E,E)-4,8-Dimethyl-10-(tetrahydropyran-2'-yloxy)-3,8-decadienecarboxylic acid 在 溶剂黄146 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 苯 为溶剂， 反应 16.0h， 生成 (3E,8E)-4,8-dimethyl-3,8-decadien-10-olide
  参考文献：
  名称：

  Stereospecific Synthesis of Suspensolide, a Male-Produced Pheromone of the Caribbean Fruit Fly, Anastrepha suspensa (Loew), and the Mexican Fruit Fly, Anastrepha ludens (Loew)

  摘要：

  An efficient synthesis of (E,E)-4,8-dimethyl-3,8-decadien-10-olide, suspensolide, a major component of the pheromone blend of the Caribbean and Mexican fruit flies, is described. The synthesis involves dicarboalumination of 1,6-heptadiyne with in situ conversion to a dialanate and reaction with paraformaldehyde. Monoprotection of the symmetrical diol formed in this process as the mono-THP derivative allowed conversion of the free hydroxyl to the chloride (NCS/DMS). Addition of one carbon to the chain was achieved by displacement of the chloride by cyanide (phase-transfer conditions) or the lithium salt of a thioorthoester. Hydrolysis of the masked carbonyls and deprotection of the omega-hydroxyl gave (E,E)-4,8-dimethyl-10-hydroxy-3,8-decadienoic acid. This diunsaturated hydroxy acid was cyclized to suspensolide in 30% yield using Mitsunobu conditions. The overall yield of suspensolide in this eight-step synthesis was 10%.

  DOI：

  10.1021/jo00096a029
• 作为产物：
  描述：

  (E,E)-9-Chloro-3,7-dimethyl-1-(tetrahydropyran-2'-yloxy)-2,7-nonadiene 在 18-冠醚-6 、 四丁基硫酸氢铵 sodium hydroxide 、 sodium peroxide 、 双氧水 作用下， 以 二氯甲烷 、 水 、 乙腈 为溶剂， 反应 28.0h， 生成 (E,E)-4,8-Dimethyl-10-(tetrahydropyran-2'-yloxy)-3,8-decadienecarboxylic acid
  参考文献：
  名称：

  Stereospecific Synthesis of Suspensolide, a Male-Produced Pheromone of the Caribbean Fruit Fly, Anastrepha suspensa (Loew), and the Mexican Fruit Fly, Anastrepha ludens (Loew)

  摘要：

  An efficient synthesis of (E,E)-4,8-dimethyl-3,8-decadien-10-olide, suspensolide, a major component of the pheromone blend of the Caribbean and Mexican fruit flies, is described. The synthesis involves dicarboalumination of 1,6-heptadiyne with in situ conversion to a dialanate and reaction with paraformaldehyde. Monoprotection of the symmetrical diol formed in this process as the mono-THP derivative allowed conversion of the free hydroxyl to the chloride (NCS/DMS). Addition of one carbon to the chain was achieved by displacement of the chloride by cyanide (phase-transfer conditions) or the lithium salt of a thioorthoester. Hydrolysis of the masked carbonyls and deprotection of the omega-hydroxyl gave (E,E)-4,8-dimethyl-10-hydroxy-3,8-decadienoic acid. This diunsaturated hydroxy acid was cyclized to suspensolide in 30% yield using Mitsunobu conditions. The overall yield of suspensolide in this eight-step synthesis was 10%.

  DOI：

  10.1021/jo00096a029

文献信息

• Mori, Kenji; Nakazono, Yutaka, Liebigs Annalen der Chemie, 1988, p. 167 - 174
  作者：Mori, Kenji、Nakazono, Yutaka

  DOI：——

  日期：——
• Stereospecific Synthesis of Suspensolide, a Male-Produced Pheromone of the Caribbean Fruit Fly, Anastrepha suspensa (Loew), and the Mexican Fruit Fly, Anastrepha ludens (Loew)
  作者：Ginna Hidalgo-Del Vecchio、Allan C. Oehlschlager

  DOI：10.1021/jo00096a029

  日期：1994.8

  An efficient synthesis of (E,E)-4,8-dimethyl-3,8-decadien-10-olide, suspensolide, a major component of the pheromone blend of the Caribbean and Mexican fruit flies, is described. The synthesis involves dicarboalumination of 1,6-heptadiyne with in situ conversion to a dialanate and reaction with paraformaldehyde. Monoprotection of the symmetrical diol formed in this process as the mono-THP derivative allowed conversion of the free hydroxyl to the chloride (NCS/DMS). Addition of one carbon to the chain was achieved by displacement of the chloride by cyanide (phase-transfer conditions) or the lithium salt of a thioorthoester. Hydrolysis of the masked carbonyls and deprotection of the omega-hydroxyl gave (E,E)-4,8-dimethyl-10-hydroxy-3,8-decadienoic acid. This diunsaturated hydroxy acid was cyclized to suspensolide in 30% yield using Mitsunobu conditions. The overall yield of suspensolide in this eight-step synthesis was 10%.