(E,E)-3,7-Dimethyl-9-(tetrahydropyran-2'-yloxy)-2,7-nonadien-1-ol | 111351-01-0

• 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-9-(tetrahydropyran-2'-yloxy)-2,7-nonadien-1-ol
• 英文别名: (2E,7E)-3,7-Dimethyl-9-(tetrahydropyranyloxy)-2,7-nonadien-1-ol；(2E,7E)-3,7-dimethyl-9-(oxan-2-yloxy)nona-2,7-dien-1-ol
• CAS: 111351-01-0
• 化学式: C₁₆H₂₈O₃
• 分子量: 268.397
• InChiKey: NBSIQOZECNKUIC-AOEKMSOUSA-N

物化性质

• 沸点：
  127-129 °C
• 密度：
  0.99±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  19
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  38.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (E,E)-3,7-Dimethyl-9-(tetrahydropyran-2'-yloxy)-2,7-nonadien-1-ol 在 N-氯代丁二酰亚胺 、 二甲基硫 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以90%的产率得到(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：

  (E)-6-acetoxy-4-methyl-4-hexenal 在 sodium hydroxide 、 copper(l) iodide 、 lithium aluminium tetrahydride 、 正丁基锂 、 lithium tri(t-butoxy)aluminum hydride 、 氨 、 lithium 、 碳酸氢钠 、 对甲苯磺酸 、 lithium bromide 作用下， 以 四氢呋喃 、 吡啶 、 乙醚 、 二氯甲烷 、 丙酮 为溶剂， 反应 88.34h， 生成 (E,E)-3,7-Dimethyl-9-(tetrahydropyran-2'-yloxy)-2,7-nonadien-1-ol
  参考文献：
  名称：

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

  摘要：

  DOI：

文献信息

• MORI, KENJI;NAKAZONO, YUTAKA, LIEBIGS ANN. CHEM.,(1988) N 2, 167-174
  作者：MORI, KENJI、NAKAZONO, YUTAKA

  DOI：——

  日期：——
• 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%.