(4Z,7Z)-1-(tetrahydropyran-2-yloxy)-4,7-decadiene | 166901-11-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧烷类
• 英文名称: (4Z,7Z)-1-(tetrahydropyran-2-yloxy)-4,7-decadiene
• 英文别名: 2-[(4Z,7Z)-deca-4,7-dienoxy]oxane
• CAS: 166901-11-7
• 化学式: C₁₅H₂₆O₂
• 分子量: 238.37
• InChiKey: VSNQOZMEYPCLNC-CWWKMNTPSA-N

物化性质

• 沸点：
  335.4±42.0 °C(Predicted)
• 密度：
  0.92±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  17
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (4Z,7Z)-1-(tetrahydropyran-2-yloxy)-4,7-decadiene 在 六甲基磷酰三胺 、 氨 、 溴 、 sodium 、 三苯基膦 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 二氯甲烷 为溶剂， 生成 (E3,Z8,Z11)-3,8,11-tetradecatrienyl alcohol
  参考文献：
  名称：

  Titanium(II)-based Z-reduction of alkynes: stereo- and regio-specific Z-dideuteriation of conjugated and methylene-skipped ynes

  摘要：

  该研究描述了以 D2O 作为氘源，通过 TiII 介导的、立体和区域特异性还原分离的、共轭的和亚甲基跳变的聚炔，并将这种方法（使用 H2O）应用于合成 (3E,8Z,11Z)-tetradeca-3,8,11-trienyl acetate（一种西红柿毁灭性害虫 Scrobipalpuloides absoluta 的主要性引诱剂）。

  DOI：

  10.1039/cc9960001697
• 作为产物：
  描述：

  2-(4-戊炔氧基)四氢-2H-吡喃 在 titanium(IV) isopropylate 、 copper(l) iodide 、 水 、 异丙基溴化镁 、 potassium carbonate 、 sodium iodide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 生成 (4Z,7Z)-1-(tetrahydropyran-2-yloxy)-4,7-decadiene
  参考文献：
  名称：

  Titanium(II)-based Z-reduction of alkynes: stereo- and regio-specific Z-dideuteriation of conjugated and methylene-skipped ynes

  摘要：

  该研究描述了以 D2O 作为氘源，通过 TiII 介导的、立体和区域特异性还原分离的、共轭的和亚甲基跳变的聚炔，并将这种方法（使用 H2O）应用于合成 (3E,8Z,11Z)-tetradeca-3,8,11-trienyl acetate（一种西红柿毁灭性害虫 Scrobipalpuloides absoluta 的主要性引诱剂）。

  DOI：

  10.1039/cc9960001697

文献信息

• Titanium(II)-based Z-reduction of alkynes. Syntheses of deuterium labelled linolenic and oleic acids and (3E,8Z,11Z )-tetradeca-3,8,11-trienyl acetate, the sex pheromone of a tomato pest, Scrobipalpuloides absoluta
  作者：Natasha L. Hungerford、William Kitching

  DOI：10.1039/a800674a

  日期：——

  An operationally simple TiII-mediated, stereo- and regio-specific reduction of isolated, conjugated and methylene ‘skipped’ polyynes to the corresponding Z-polyenes in a one-pot procedure is described and applied inter alia to the syntheses of deuterium labelled linolenic and oleic acids. Final quenching with D2O (instead of H2O) results in regio- and stereo-specific Z-dideuteration of the alkyne. The synthesis of (3E,8Z,11Z)-tetradeca-3,8,11-trienyl acetate, the major sex pheromone of Scrobipalpuloides absoluta, a destructive pest of tomatoes, and the (3Z,8Z,11Z)-isomer, utilises this methodology in key reduction steps, and under- or over-reduction are negligible.

  本文描述了一种操作简便的TiII介导的一锅法立体和区域选择性还原孤立共轭亚甲基跳跃多炔烃至相应的Z-多烯烃的方法，并应用于氘标记亚麻酸和油酸的合成。最终用D2O（而非H2O）淬灭反应，实现了炔烃的区域和立体选择性双氘化。(3E,8Z,11Z)-十四碳-3,8,11-三烯基乙酸酯（主要性信息素）和(3Z,8Z,11Z)异构体的合成，利用了这种方法在关键还原步骤中，且不足或过度还原的情况可忽略不计。
• Process for preparing (4Z,7Z)-4,7-decadien-1-yl acetate
  申请人：SHIN-ETSU CHEMICAL CO., LTD.

  公开号：US10221123B1

  公开（公告）日：2019-03-05

  A high-yield process for preparing (4Z,7Z)-4,7-decadien-1-yl acetate, with reduced number of steps, without using a protecting group. A process for preparing (4Z,7Z)-4,7-decadien-1-yl acetate is provided, the process including at least the following steps: reducing a 10-halo-3,6-decadiyne of the general formula (1) to form a (3Z,6Z)-10-halo-3,6-decadiene of the general formula (2); and converting the (3Z,6Z)-10-halo-3,6-decadiene into (4Z,7Z)-4,7-decadien-1-yl acetate of the formula (4) having an acetoxy group in place of the halogen atom of the (3Z,6Z)-10-halo-3,6-decadiene.

  提供了一种制备(4Z,7Z)-4,7-癸二烯-1-醋酸酯的高产率工艺，步骤减少，无需使用保护基团。制备(4Z,7Z)-4,7-癸二烯-1-醋酸酯的工艺包括至少以下步骤：将通式(1)的10-卤代-3,6-癸二炔还原以形成通式(2)的(3Z,6Z)-10-卤代-3,6-癸二烯；将(3Z,6Z)-10-卤代-3,6-癸二烯转化为具有乙酰氧基取代(3Z,6Z)-10-卤代-3,6-癸二烯卤原子的通式(4)的(4Z,7Z)-4,7-癸二烯-1-醋酸酯。
• Tetradecatrienyl and tetradecadienyl acetates and their use as sex
  申请人：Cornell Research Foundation, Inc.

  公开号：US05728376A1

  公开（公告）日：1998-03-17

  The present invention is directed to compounds useful as moth attractants and to methods for controlling populations of the tomato moth Scrobipalpuloides absoluta with these compounds. The compounds are 3,8,11-tetradecatrienyl acetates, 3,8-tetradecadienyl acetates, 3,11-tetradecadienyl acetates, and 8,11-tetradecadienyl acetates. Preferred compounds are (3E,8Z,11Z)-3,8,11-tetradecatrienyl acetate, (3E,8Z)-3,8-tetradecadienyl acetate, (3E,11Z)-3,11 -tetradecadienyl acetate, and (8Z,11Z)-8-11-tetradecadienyl acetate. The compounds can be used as an attractant in moth traps comprising, in addition to the compounds, a moth restraint. Alternatively, the compounds of the present invention can be combined with a biocontrol agent or an insecticide for use as a moth control composition. Synthesis of (3E,8Z,11Z)-3,8,11-tetradecatrienyl acetate is described.

  本发明涉及用于吸引飞蛾的化合物以及使用这些化合物控制番茄飞蛾Scrobipalpuloides absoluta种群的方法。这些化合物是3,8,11-四十四碳烯酸乙酯，3,8-四十四碳二烯酸乙酯，3,11-四十四碳二烯酸乙酯和8,11-四十四碳二烯酸乙酯。首选化合物是(3E,8Z,11Z)-3,8,11-四十四碳烯酸乙酯，(3E,8Z)-3,8-四十四碳二烯酸乙酯，(3E,11Z)-3,11-四十四碳二烯酸乙酯和(8Z,11Z)-8-11-四十四碳二烯酸乙酯。这些化合物可以用作飞蛾诱捕器中的诱引剂，除了化合物外，还包括飞蛾约束器。或者，本发明的化合物可以与生物控制剂或杀虫剂结合使用，用作飞蛾控制组合物。描述了(3E,8Z,11Z)-3,8,11-四十四碳烯酸乙酯的合成方法。
• PROCESS FOR PREPARING (4Z,7Z)-4,7-DECADIEN-1-YL ACETATE
  申请人：Shin-Etsu Chemical Co., Ltd.

  公开号：EP3453699A1

  公开（公告）日：2019-03-13

  One object of the invention is to provide a high-yield process for preparing (4Z,7Z)-4,7-decadien-1-yl acetate, with reduced number of steps, without using a protecting group. A process for preparing (4Z,7Z)-4,7-decadien-1-yl acetate is provided, the process comprising at least the following steps: reducing a 10-halo-3,6-decadiyne of the general formula (1) to form a (3Z,6Z)-10-halo-3,6-decadiene of the general formula (2); and converting the (3Z,6Z)-10-halo-3,6-decadiene into (4Z,7Z)-4,7-decadien-1-yl acetate of the formula (4) having an acetoxy group in place of the halogen atom of the (3Z,6Z)-10-halo-3,6-decadiene.

  本发明的一个目的是提供一种高产率的制备(4Z,7Z)-4,7-癸二烯-1-基乙酸酯的工艺，该工艺减少了步骤，无需使用保护基团。 本发明提供了一种制备 (4Z,7Z)-4,7-癸二烯-1-基乙酸酯的工艺，该工艺至少包括以下步骤：还原通式（1）的 10-卤代-3,6-癸二烯，生成通式（2）的 (3Z,6Z)-10-卤代-3,6-癸二烯；并将(3Z,6Z)-10-卤-3,6-癸二烯转化为通式(4)的(4Z,7Z)-4,7-癸二烯-1-基乙酸酯，其乙酰氧基取代了(3Z,6Z)-10-卤-3,6-癸二烯的卤原子。
• Identification of the sex pheromone of the lesser date moth, Batrachedra amydraula, using sequential SPME auto-sampling
  作者：Anat Levi-Zada、Daniela Fefer、Leonid Anshelevitch、Anna Litovsky、Marie Bengtsson、Galina Gindin、Victoria Soroker

  DOI：10.1016/j.tetlet.2011.06.091

  日期：2011.8

  The identification of the sex pheromone of the lesser date moth, Batrachedra amydraula (Meyrick) was based on GC-MS analysis of volatiles released by virgin females using sequential SPME auto-sampling of headspace and by synthesis of the key component, (4Z,7Z)-4,7-decadien-1-yl acetate. Substantial capture of males in a date palm plantation using a bait consisting of the key component and 5Z-decen-1-yl acetate in a ratio of 1:2 indicated that these are the essential components of the sex pheromone. Addition of 4Z-decen-1-yl acetate and decan-1-yl acetate, which were also identified, did not affect trap-capture. The lesser date moth is the first member of the Batrachedridae whose sex pheromone has been identified. (4Z,7Z)-4,7-Decadien-1-yl acetate is a novel compound among moth sex pheromones. (C) 2011 Elsevier Ltd. All rights reserved.