(4E,6E)-nona-4,6-dien-1-ol

• 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: (4E,6E)-nona-4,6-dien-1-ol
• 化学式: C₉H₁₆O
• 分子量: 140.225
• InChiKey: ZTELSJAVXJTPQO-VNKDHWASSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  10
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  四氢呋喃-2-甲醛 在 正丁基锂 、 potassium tert-butylate 作用下， 以 四氢呋喃 为溶剂， 反应 4.0h， 生成 (4E,6E)-nona-4,6-dien-1-ol
  参考文献：
  名称：

  Mixed metal base LICKOR as key reagent in the synthesis of conjugate alkadien-1-ols. A new route to an insect attractant

  摘要：

  Tetrahydrofurfuryl alcohol has been oxidized to the corresponding aldehyde (1) using TPAP and NMO. Subsequent Wittig reaction afforded 2-alk-1-enyltetrahydrofurans (2 and 3) that on be metalated with Schlosser's reagent LICKOR. The base promotes the 1,4-eliminative ring fission, affording conjugate alkadien-1-ols (4 and 5) with high all E stereoselectivity. In the case of 2-pent-1-enyltetrahydrofuran, elimination reaction gives (4E, 6E)-nona-4,6-dien-1-ol (5), which is structurally related to two sex pheromone components of the Caribbean fruit ny, Anastrepha suspensa. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(98)00918-1

文献信息

• Mixed metal base LICKOR as key reagent in the synthesis of conjugate alkadien-1-ols. A new route to an insect attractant
  作者：Fulvio Cominetti、Annamaria Deagostino、Cristina Prandi、Paolo Venturello

  DOI：10.1016/s0040-4020(98)00918-1

  日期：1998.11

  Tetrahydrofurfuryl alcohol has been oxidized to the corresponding aldehyde (1) using TPAP and NMO. Subsequent Wittig reaction afforded 2-alk-1-enyltetrahydrofurans (2 and 3) that on be metalated with Schlosser's reagent LICKOR. The base promotes the 1,4-eliminative ring fission, affording conjugate alkadien-1-ols (4 and 5) with high all E stereoselectivity. In the case of 2-pent-1-enyltetrahydrofuran, elimination reaction gives (4E, 6E)-nona-4,6-dien-1-ol (5), which is structurally related to two sex pheromone components of the Caribbean fruit ny, Anastrepha suspensa. (C) 1998 Elsevier Science Ltd. All rights reserved.