(4Z,6E)-14-(tert-Butoxy)tetradeca-4,6-diene | 247167-81-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (4Z,6E)-14-(tert-Butoxy)tetradeca-4,6-diene
• 英文别名: (4Z,6E)-14-[(2-methylpropan-2-yl)oxy]tetradeca-4,6-diene
• CAS: 247167-81-3
• 化学式: C₁₈H₃₄O
• 分子量: 266.467
• InChiKey: UCRZRMLNOKAYFA-UQGDGPGGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.4
• 重原子数：
  19
• 可旋转键数：
  12
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (4Z,6E)-14-(tert-Butoxy)tetradeca-4,6-diene 在 sodium hydroxide 、 sodium acetate 、 三氯化铁 、 pyridinium chlorochromate 作用下， 以 甲醇 、 乙醚 、 二氯甲烷 为溶剂， 反应 37.5h， 生成 (8E,10Z)-tetradeca-8,10-dienal
  参考文献：
  名称：

  Synthesis of (8E,10Z)-Tetradeca-8,10-dienal, Sex Pheromone of Horse Chestnut Leafminer (Cameraria ohridella), and All Its Geometrical Isomers

  摘要：

  (8E,10Z)-十四碳八烯醛（1a），是马栗叶蛾（Cameraria ohridella；鳞翅目，柳小蜂科）的性信息素，其几何异构体（1b-1d）通过使用四(三苯基膦)钯催化的烯烃或烯基铝烷与相应的乙烯基碘化物进行交叉偶联反应进行了高效合成。所得到的十四碳八烯醛1a-1d的立体异构纯度高于95%（气相色谱法）。在雄性触角上引发的所制备化合物1a-1d的相对电子触角（EAG）活性支持了先前发表的对C. ohridella性信息素的鉴定。

  DOI：

  10.1135/cccc20000511
• 作为产物：
  描述：

  7-溴-1-庚醇 在 四(三苯基膦)钯 copper (I) iodide 、 Amberlyst H-15 、 bis(cyclohexanyl)borane 、 碘 、 二异丁基氢化铝 、 正丁胺 作用下， 以 四氢呋喃 、 正己烷 、 二甲基亚砜 、 苯 为溶剂， 反应 29.0h， 生成 (4Z,6E)-14-(tert-Butoxy)tetradeca-4,6-diene
  参考文献：
  名称：

  Synthesis of (8E,10Z)-Tetradeca-8,10-dienal, Sex Pheromone of Horse Chestnut Leafminer (Cameraria ohridella), and All Its Geometrical Isomers

  摘要：

  (8E,10Z)-十四碳八烯醛（1a），是马栗叶蛾（Cameraria ohridella；鳞翅目，柳小蜂科）的性信息素，其几何异构体（1b-1d）通过使用四(三苯基膦)钯催化的烯烃或烯基铝烷与相应的乙烯基碘化物进行交叉偶联反应进行了高效合成。所得到的十四碳八烯醛1a-1d的立体异构纯度高于95%（气相色谱法）。在雄性触角上引发的所制备化合物1a-1d的相对电子触角（EAG）活性支持了先前发表的对C. ohridella性信息素的鉴定。

  DOI：

  10.1135/cccc20000511

文献信息

• (E8,Z10)-TETRADECA-8,10-DIENAL, THE METHOD OF ITS PREPARATION AND ITS USE AS SEXUAL ATTRACTANT FOR LEAFMINER MOTHS
  申请人：Ustav Organicke Chemie A Biochemie Akademie Ved Ceske Republiky

  公开号：EP1192117B1

  公开（公告）日：2004-09-01
• Identification of a new lepidopteran sex pheromone in picogram quantities using an antennal biodetector: (8E,10Z)-tetradeca-8,10-dienal from Cameraria ohridella
  作者：Aleš Svatoš、Blanka Kalinová、Michal Hoskovec、Jiří Kindl、Oldřich Hovorka、Ivan Hrdý

  DOI：10.1016/s0040-4039(99)01426-4

  日期：1999.9

  A major sex attractant released by the virgin female of the horse-chestnut leafminer Cameraria ohridella Deschka et Dimic (Lepidoptera: Gracillariidae) which devastates horse-chestnut trees in Europe, was identified in picogram quantities as (8E,10Z)-tetradeca-8,10-dienal without using spectral methods. The identification solely relied on gas chromatography with electroantennographic detection (GC-EAD), calculation of Kovats' indices of the active principle on different GC phases, and construction of antennal response spectra (EAG response profiles) to C-12 and C-14 saturated and unsaturated standards with different functional groups. The dienal was prepared by a stereospecific synthesis and shown to be highly active for conspecific males in pg amounts and Fully comparable to the natural substance. (C) 1999 Elsevier Science Ltd. All rights reserved.
• TETRADECA-8,10-DIENALS, THE METHOD OF PREPARATION THEREOF AND THEIR USE AS SEXUAL ATTRACTANTS FOR LEAFMINER MOTHS
  申请人：Ustav Organicke Chemie A Biochemie Akademie Ved Ceske Republiky

  公开号：EP1192117A1

  公开（公告）日：2002-04-03
• [EN] TETRADECA-8,10-DIENALS, THE METHOD OF PREPARATION THEREOF AND THEIR USE AS SEXUAL ATTRACTANTS FOR LEAFMINER MOTHS<br/>[FR] TETRADECA-8,10-DIENALS, PROCEDE DE PREPARATION DESDITES SUBSTANCES ET LEUR UTILISATION EN TANT QU'ATTRACTIFS SEXUELS POUR LES TEIGNES MINEUSES DES FEUILLES
  申请人：USTAV ORGANICKE CHEMIE A BIOCH

  公开号：WO2001000553A1

  公开（公告）日：2001-01-04

  The subject of the invention are isomerically pure tetradeca-8,10-dienals, the synthetic preparation thereof and their use as sex attractants for leafminers of the genus Gracillariidae (Lepidotpera, Insecta), in particular the means of preparation of the (E8,Z10)-tetradeca-8,10-dienal and its utilization as a sex attractant for horse chestnut leafminer [Cameraria ohridella Deschka et Dimić 1985 (Lepidoptera:Gracillariidae)]. The title compound can be prepared so that (E)-9-(tert-butoxy)-1-jodnon-1-ene reacts with 1-pentyne in a basic solvent, preferably an alkylamine, in the presence of a Pd(0) catalyst mixed with a cuprous salt providing (E))-14-(tert-butoxy)tetradec-6-en-4-yne, whereupon the above prepared enyne is reduced to provide (4Z,6E)-14-(tert-butoxy)tetradeca-4,6-diene, then a protection group is removed in an acidic environment and the prepared (8E,10Z)-tetradeca-8,10-dien-1-ol is further oxidized to give the (E8,Z10)-tetradeca-8,10-dienal. This compound is directly, in a solution or in a mixture with additional compounds, or in the form of its pro-pheromone derivatives, applied on an appropriate support and then used in diverse types of traps containing, beside the attractant, a moth restraint to control populations of the horse chestnut leafminer, or in mass-trapping devices for the moth males or in devices containing, beside the attractant, insecticides, a biocontrol agent, or compounds regulating insect development (IGR-Insect Growth Regulators), in which the attracted males are killed, or agents spread into leafminer populations, or, finally, the title compound can be dispersed into the atmosphere in concentrations capable of confusing the males and thus preventing their copulation with conspecific females.
• Synthesis of (8E,10Z)-Tetradeca-8,10-dienal, Sex Pheromone of Horse Chestnut Leafminer (Cameraria ohridella), and All Its Geometrical Isomers
  作者：Michal Hoskovec、David Šaman、Aleš Svatoš

  DOI：10.1135/cccc20000511

  日期：——

  (8E,10Z)-Tetradeca-8,10-dienal (1a), sex pheromone of the horse chestnut leafminer (Cameraria ohridella; Lepidoptera, Gracillariidae), and its geometrical isomers (1b-1d) were efficiently synthesized using tetrakis(triphenylphosphine)palladium catalyzed cross-coupling reactions of alk-1-ynes or alkenyl alanes with corresponding vinyl iodides. The stereoisomeric purity of obtained tetradecadienals 1a-1d was higher than 95% (GC). Relative electroantennographic (EAG) activities of the prepared compounds 1a-1d elicited on male antennae supported the previously published identification of the C. ohridella sex pheromone.

  (8E,10Z)-十四碳八烯醛（1a），是马栗叶蛾（Cameraria ohridella；鳞翅目，柳小蜂科）的性信息素，其几何异构体（1b-1d）通过使用四(三苯基膦)钯催化的烯烃或烯基铝烷与相应的乙烯基碘化物进行交叉偶联反应进行了高效合成。所得到的十四碳八烯醛1a-1d的立体异构纯度高于95%（气相色谱法）。在雄性触角上引发的所制备化合物1a-1d的相对电子触角（EAG）活性支持了先前发表的对C. ohridella性信息素的鉴定。