(4Z,9Z)-tetradeca-4,9-dien-1-ol | 108609-20-7

• 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: (4Z,9Z)-tetradeca-4,9-dien-1-ol
• 英文别名: tetradeca-(4Z,9Z)-4,9-dien-1-ol；(Z)-4,(Z)-9-Tetradecadien-1-ol；(Z4,Z9)-tetradecadienol
• CAS: 108609-20-7
• 化学式: C₁₄H₂₆O
• 分子量: 210.36
• InChiKey: RTVRBZVCOFYNLX-VIFBMRGNSA-N

物化性质

• 沸点：
  312.0±11.0 °C(Predicted)
• 密度：
  0.860±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  15
• 可旋转键数：
  10
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (4Z,9Z)-tetradeca-4,9-dien-1-ol 在 copper(l) iodide 、 magnesium 、 三氟乙酸酐 、 lithium bromide 作用下， 反应 4.75h， 生成 (6Z,11Z)-hexadeca-6,11-dien-1-ol
  参考文献：
  名称：

  通过镍催化的格氏反应可高效，立体选择性地合成昆虫信息素。Eudia pavonia和Droxophila melanogaster的棉酚和信息素的合成。

  摘要：

  三种信息素，（6Z，11Z）-十六烷基-6,11-二烯-1-基乙酸酯（得自Eudia pavonia），（5Z，9Z）-heptacosa-5,9-diene（得自果蝇（Drosophila melanogaster））和棉酚已经制成。通过镍与环烯醇醚进行的格氏反应的两个连续结果，并从所得的醇制备格氏试剂，合成了每一种。

  DOI：

  10.1016/s0040-4020(01)88230-2
• 作为产物：
  描述：

  2-(4-戊炔氧基)四氢-2H-吡喃 在 nickel diacetate sodium tetrahydroborate 、 正丁基锂 、 氢气 、 对甲苯磺酸 、 乙二胺 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 为溶剂， 反应 18.17h， 生成 (4Z,9Z)-tetradeca-4,9-dien-1-ol
  参考文献：
  名称：

  摘要：

  The Iepidopteran genus Saturnia has three representatives in North America, S. walterorum, S.mendocino, and S. albofasciata. (E4,Z9)-Tetradecadienal (E4,Z9-14 : Ald) was identified as a sex pheromone component for all three species by combinations of coupled gas chromatography-electroantennogram detection (GC-EAD), GC-mass spectrometry (MS), and field trials. In field trials, all three species were strongly attracted to (E4,Z9-14 : Ald) as a single component. Small amounts of (Z)-9-tetradecenal (Z9-14: Ald) also were found in extracts of all three species, but blends of this compound with E4,Z9-14 : Aid were no more attractive to male moths than E4,Z9-14 : Aid alone. Extracts of pheromone glands of female S. walterorum occasionally contained a third, trace compound eliciting responses from male antennae in GC-EAD experiments, but this compound was not identified. It is suggested that the three species can use the same, single component as a sex attractant because the flight period of S. albofasciata (Fall) is different than that of the other two species (spring), whereas the geographic distributions of S. mendocino and S. walterorum overlap over only small portions of their ranges. Furthermore, the latter two species readily hybridize, so there may be minimal fitness cost to cross-attraction.

  DOI：

  10.1023/a:1010310204552

文献信息

• Short, regio- and stereo-selective preparation of 1,5- and 1,6-dienes. Syntheses of eudia pavonia pheromone and gossyplure.
  作者：Jean-Philippe Ducoux、Patrick Le Ménez、Nicole Kunesch、Gerhard Kunesch、Ernest Wenkert

  DOI：10.1016/0040-4039(90)80134-8

  日期：1990.1

  gossyplure, have been synthesized each by two consecutive sequences of nickel-assisted Grignard reactions with cyclic enol ethers and the preparation of Grignard reagents from the resultant alcohols, followed each by copper-promoted Grignard reaction with a small-ring ether and subsequent acetylation.

  两种信息素，（Z）-6，（Z）-11-hexadecadien-1- ylacetate（购自Eudia pavonia）和棉酚，是通过连续两个连续的镍辅助格氏反应与环烯醇醚合成的，分别合成了从所得醇中分离出格氏试剂，然后分别与小环醚进行铜促进的格氏反应，然后进行乙酰化反应。
• Tomida, Ichiro; Iwakoshi, Kenji; Kono, Satoshi, Agricultural and Biological Chemistry, 1987, vol. 51, # 3, p. 939 - 940
  作者：Tomida, Ichiro、Iwakoshi, Kenji、Kono, Satoshi、Takahashi, Takeshi、Matsunaga, Taiki、Kayahara, Hiroshi

  DOI：——

  日期：——
• DUCOUX, JEAN-PHILIPPE;LE, MENEZ PATRICK;KUNESCH, NICOLE;KUNESCH, GERHARD;+, TETRAHEDRON LETT., 31,(1990) N8, C. 2595-2598
  作者：DUCOUX, JEAN-PHILIPPE、LE, MENEZ PATRICK、KUNESCH, NICOLE、KUNESCH, GERHARD、+

  DOI：——

  日期：——
• US9981898B1
  申请人：——

  公开号：US9981898B1

  公开（公告）日：2018-05-29
• ——
  作者：J. STEVEN McELFRESH、JOCELYN G. MILLAR、DANIEL RUBINOFF

  DOI：10.1023/a:1010310204552

  日期：——

  The Iepidopteran genus Saturnia has three representatives in North America, S. walterorum, S.mendocino, and S. albofasciata. (E4,Z9)-Tetradecadienal (E4,Z9-14 : Ald) was identified as a sex pheromone component for all three species by combinations of coupled gas chromatography-electroantennogram detection (GC-EAD), GC-mass spectrometry (MS), and field trials. In field trials, all three species were strongly attracted to (E4,Z9-14 : Ald) as a single component. Small amounts of (Z)-9-tetradecenal (Z9-14: Ald) also were found in extracts of all three species, but blends of this compound with E4,Z9-14 : Aid were no more attractive to male moths than E4,Z9-14 : Aid alone. Extracts of pheromone glands of female S. walterorum occasionally contained a third, trace compound eliciting responses from male antennae in GC-EAD experiments, but this compound was not identified. It is suggested that the three species can use the same, single component as a sex attractant because the flight period of S. albofasciata (Fall) is different than that of the other two species (spring), whereas the geographic distributions of S. mendocino and S. walterorum overlap over only small portions of their ranges. Furthermore, the latter two species readily hybridize, so there may be minimal fitness cost to cross-attraction.