1-(tetrahydropyran-2-yloxy)-4,7-decadiyne | 166901-10-6

• 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: 1-(tetrahydropyran-2-yloxy)-4,7-decadiyne
• 英文别名: 2-deca-4,7-diynyloxy-tetrahydro-pyran；2-Deca-4,7-diynoxyoxane
• CAS: 166901-10-6
• 化学式: C₁₅H₂₂O₂
• 分子量: 234.338
• InChiKey: WDDDZLQXFTXNJC-UHFFFAOYSA-N

物化性质

• 沸点：
  357.4±42.0 °C(Predicted)
• 密度：
  0.98±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  17
• 可旋转键数：
  4
• 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：

  1-(tetrahydropyran-2-yloxy)-4,7-decadiyne 在 喹啉 作用下， 以 二氯甲烷 为溶剂， 生成 (4Z,7Z)-4,7-decadien-1-yl acetate
  参考文献：
  名称：

  Identification of the sex pheromone of the lesser date moth, Batrachedra amydraula, using sequential SPME auto-sampling

  摘要：

  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.

  DOI：

  10.1016/j.tetlet.2011.06.091
• 作为产物：
  描述：

  2-戊炔-1-醇 在 氢氧化钾 、 copper(I) bromide dimethylsulfide complex 、 乙基溴化镁 作用下， 反应 1.5h， 生成 1-(tetrahydropyran-2-yloxy)-4,7-decadiyne
  参考文献：
  名称：

  (3E,8Z,11Z)-3,8,11-Tetradecatrienyl acetate, major sex pheromone component of the tomato pest Scrobipalpuloides absoluta (Lepidoptera: Gelechiidae)

  摘要：

  The major sex attractant emitted by Scrobipalpuloides absoluta females is shown to be (3E,8Z,11Z)-3,8,11-tetradecatrien-1-yl acetate by a novel strategy involving the random reduction of double bonds, followed by methylthiolation of the reduced products. Each female sex gland contains ca. 1-5 ng of this pheromone. This triene ester, synthesized by a stereospecific procedure, shows spectral and gas chromatographic properties identical to those of the natural substance. In field tests and wind tunnel bioassays, the synthetic ester was found to be highly attractive to conspecific males. The male response to this pheromone, however, is restricted to the same early-morning time window during which females exhibit calling behavior. Copyright (C) 1996 Elsevier Science Ltd

  DOI：

  10.1016/0968-0896(96)00007-7

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。
• New Method Based on 1-(Trimethysilyl)alk-1-yne To Prepare 1,4-Skipped Diynes
  作者：Florian Montel、Renaud Beaudegnies、Jilali Kessabi、Benjamin Martin、Eric Muller、Sebastian Wendeborn、Pierre M. J. Jung

  DOI：10.1021/ol0604670

  日期：2006.4.1

  of a fluoride source and a catalytic amount of copper iodide to prepare 1,4-skipped diynes with good yields and in mild conditions. We have shown that this reaction also works very well with germanium and tin derivatives as an alternative to silicon. This new method can be useful for the synthesis of polyunsaturated fatty acids.

  [反应：参见正文]我们已经开发了一种新型TMS-炔烃与炔丙基卤之间的新型反应，该反应在氟化物源和催化量的碘化铜的存在下制备了1,4跳过的二炔，具有良好的收率和温和的反应。情况。我们已经表明，该反应对于锗和锡衍生物作为硅的替代品也非常有效。这种新方法可用于合成多不饱和脂肪酸。
• Titanium(II)-based Z-reduction of alkynes: stereo- and regio-specific Z-dideuteriation of conjugated and methylene-skipped ynes
  作者：Natasha L. Hungerford、William Kitching

  DOI：10.1039/cc9960001697

  日期：——

  A TiII-mediated, stereo- and regio-specific reduction of isolated, conjugated and methylene skipped poly-ynes to the corresponding Z-dideuterio polyenes in a one-pot procedure with D2O as deuterium source is described, and this methodology (using H2O) is applied to the synthesis of (3E,8Z,11Z)-tetradeca-3,8,11-trienyl acetate, the major sex attractant of Scrobipalpuloides absoluta, a destructive pest of tomatoes.

  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）。
• 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。