(5E)-4,4,7-trimethylocta-1,5,7-triene | 1380584-39-3

• 分子结构分类: 有机化合物 - 碳氢化合物 - 不饱和烃
• 英文名称: (5E)-4,4,7-trimethylocta-1,5,7-triene
• CAS: 1380584-39-3
• 化学式: C₁₁H₁₈
• 分子量: 150.264
• InChiKey: FEDDGOFDFLGCBZ-VQHVLOKHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.72
• 重原子数：
  11.0
• 可旋转键数：
  4.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  0.0
• 氢给体数：
  0.0
• 氢受体数：
  0.0

反应信息

• 作为反应物：
  描述：

  (5E)-4,4,7-trimethylocta-1,5,7-triene 、 丙烯醛 在 zinc(II) chloride 作用下， 以 二氯甲烷 为溶剂， 生成 (1RS,2RS)-1-formyl-2-(1',1'-dimethylbut-3'-enyl)-4-methylcyclohex-3-ene 、 (1SR,2RS)-1-formyl-2-(1',1'-dimethylbut-3'-enyl)-4-methylcyclohex-3-ene
  参考文献：
  名称：

  A diastereoselective synthesis of (1SR,3SR,7RS)-3-methyl-α-himachalene, the sex pheromone of the sandfly, Lutzomyia longipalpis (Diptera: Psychodidae)

  摘要：

  The sandfly, Lutzomyia longipalpis, vectors the causative agent of visceral leishmaniasis in the New World. The male-produced pheromone, (1S,3S,7R)-3-methyl-alpha-himachalene provides an opportunity for pest managing this pest problem by influencing the behaviour of the biting female. Previous syntheses of the pheromone have all focused on a late stage Diels-Alder cyclisation to generate the bicyclic cis-himachalene skeleton. By adopting a new retrosynthetic analysis that depends on an early stage Diels-Alder cyclisation, the number of steps has been reduced to ten, of which five are catalytic and so provides access to quantities suitable for field-scale experiments. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2012.04.037
• 作为产物：
  描述：

  (±)-菊醇 在 正丁基锂 、 四丙基高钌酸铵 、 对甲苯磺酸 、 N-甲基吗啉氧化物 作用下， 以 四氢呋喃 、 二氯甲烷 、 苯 为溶剂， 反应 6.0h， 生成 (5E)-4,4,7-trimethylocta-1,5,7-triene
  参考文献：
  名称：

  A diastereoselective synthesis of (1SR,3SR,7RS)-3-methyl-α-himachalene, the sex pheromone of the sandfly, Lutzomyia longipalpis (Diptera: Psychodidae)

  摘要：

  The sandfly, Lutzomyia longipalpis, vectors the causative agent of visceral leishmaniasis in the New World. The male-produced pheromone, (1S,3S,7R)-3-methyl-alpha-himachalene provides an opportunity for pest managing this pest problem by influencing the behaviour of the biting female. Previous syntheses of the pheromone have all focused on a late stage Diels-Alder cyclisation to generate the bicyclic cis-himachalene skeleton. By adopting a new retrosynthetic analysis that depends on an early stage Diels-Alder cyclisation, the number of steps has been reduced to ten, of which five are catalytic and so provides access to quantities suitable for field-scale experiments. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2012.04.037

文献信息

• A diastereoselective synthesis of (1SR,3SR,7RS)-3-methyl-α-himachalene, the sex pheromone of the sandfly, Lutzomyia longipalpis (Diptera: Psychodidae)
  作者：Samuel Dufour、Pascalie Castets、John A. Pickett、Antony M. Hooper

  DOI：10.1016/j.tet.2012.04.037

  日期：2012.6

  The sandfly, Lutzomyia longipalpis, vectors the causative agent of visceral leishmaniasis in the New World. The male-produced pheromone, (1S,3S,7R)-3-methyl-alpha-himachalene provides an opportunity for pest managing this pest problem by influencing the behaviour of the biting female. Previous syntheses of the pheromone have all focused on a late stage Diels-Alder cyclisation to generate the bicyclic cis-himachalene skeleton. By adopting a new retrosynthetic analysis that depends on an early stage Diels-Alder cyclisation, the number of steps has been reduced to ten, of which five are catalytic and so provides access to quantities suitable for field-scale experiments. (C) 2012 Elsevier Ltd. All rights reserved.