(E,E)-3,7-Dimethyl-2,7-nonadiene-1,9-diol | 135159-15-8

• 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)-3,7-Dimethyl-2,7-nonadiene-1,9-diol
• 英文别名: (2E,7E)-3,7-dimethylnona-2,7-diene-1,9-diol
• CAS: 135159-15-8
• 化学式: C₁₁H₂₀O₂
• 分子量: 184.279
• InChiKey: YSMAELYBGWNMDW-JMQWPVDRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  13
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (E,E)-3,7-Dimethyl-2,7-nonadiene-1,9-diol 在 四氯化碳 、 对甲苯磺酸 、 三苯基膦 作用下， 以 乙醚 为溶剂， 生成 (E,E)-9-Chloro-3,7-dimethyl-1-(tetrahydropyran-2'-yloxy)-2,7-nonadiene
  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：

  2-(1-甲基乙烯)环氧乙烷 在 palladium diacetate 、 三异丙基亚磷酸酯 disodium hydrogenphosphate 、 sodium amalgam 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 6.0h， 生成 (E,E)-3,7-Dimethyl-2,7-nonadiene-1,9-diol
  参考文献：
  名称：

  Regioselective joining of prenyl units. A simple strategy for geometry control in Pd catalyzed allylic alkylations

  摘要：

  Either E,E-3,9-dimethylundecadien-1,11-diol or its E,Z-isomer is selectively available via Pd catalyzed allylic alkylation as a function of alkylating agent and catalyst - an observation that establishes that reactions of vinyl epoxides and their related vinyl carbonates do not proceed through a common intermediate.

  DOI：

  10.1016/s0040-4039(00)79677-8

文献信息

• 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%.
• Regioselective joining of prenyl units. A simple strategy for geometry control in Pd catalyzed allylic alkylations
  作者：Barry M. Trost、Juan R. Granja

  DOI：10.1016/s0040-4039(00)79677-8

  日期：1991.5

  Either E,E-3,9-dimethylundecadien-1,11-diol or its E,Z-isomer is selectively available via Pd catalyzed allylic alkylation as a function of alkylating agent and catalyst - an observation that establishes that reactions of vinyl epoxides and their related vinyl carbonates do not proceed through a common intermediate.