(E)-14-(tert-butoxy)tetradec-6-en-4-yne | 247167-80-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (E)-14-(tert-butoxy)tetradec-6-en-4-yne
• 英文别名: (E)-14-[(2-methylpropan-2-yl)oxy]tetradec-6-en-4-yne
• CAS: 247167-80-2
• 化学式: C₁₈H₃₂O
• 分子量: 264.451
• InChiKey: PRVUNTHYDMQRJW-MDZDMXLPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.1
• 重原子数：
  19
• 可旋转键数：
  10
• 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：

  (E)-14-(tert-butoxy)tetradec-6-en-4-yne 在 bis(cyclohexanyl)borane 、 溶剂黄146 作用下， 以 四氢呋喃 为溶剂， 反应 16.0h， 以69%的产率得到(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
• 作为产物：
  描述：

  7-溴-1-庚醇 在 四(三苯基膦)钯 copper (I) iodide 、 Amberlyst H-15 、 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 13.0h， 生成 (E)-14-(tert-butoxy)tetradec-6-en-4-yne
  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

• Stereoselective Reduction of Conjugated and Non-conjugated Triple Bonds in Attractant Precursors with Zn Activated by Cu: A Designed Approach to the Synthesis of Conjugated Dienic Pheromones
  作者：Jacek Grodner

  DOI：10.1055/s-0042-1751573

  日期：2024.7

  A simple, highly stereoselective, and efficient method to obtain important attractants by the reduction of the triple bond in several E-enynes and hex-3-ynyl acetate by an activated Zn-Cu system is described. The stereoselectivity of the semireduction for the generation of a new (Z)-C=C bond was >98%. The substrates for the reduction reaction were obtained by new synthetic routes with an overall yield

  描述了一种简单、高度立体选择性且有效的方法，通过活化的 Zn-Cu 体系还原几个E-烯炔和乙酸己-3-炔酯中的三键来获得重要的引诱剂。半还原生成新的 ( Z )-C=C 键的立体选择性>98%。通过新的合成路线获得了还原反应的底物，总收率超过40%。
• An alternative synthesis of (8E,10Z)-tetradeca-8,10-dienal, sex pheromone of horse-chestnut leafminer (Cameraria ohridella)
  作者：Jacek Grodner

  DOI：10.1016/j.tet.2008.12.044

  日期：2009.2

  The stereoselective synthesis of the sex pheromone of horse-chestnut leafminer was efficiently carried out using methodology based on the Pd(0)-catalyzed cross-coupling of 1-pentynylmagnesium bromide with the corresponding vinyl iodides as the key step. (C) 2009 Elsevier Ltd. All rights reserved.
• (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