12-chloro-1,1-diethoxy-dodec-2-yne | 109819-75-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 12-chloro-1,1-diethoxy-dodec-2-yne
• 英文别名: 12-chloro-1,1-diethoxy-2-dodecyne；12-Chloro-1,1-diethoxydodec-2-yne
• CAS: 109819-75-2
• 化学式: C₁₆H₂₉ClO₂
• 分子量: 288.858
• InChiKey: WBUVDLDNIOWTCO-UHFFFAOYSA-N

物化性质

• 沸点：
  107-110 °C(Press: 10-14 Torr)
• 密度：
  0.961±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  19
• 可旋转键数：
  12
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.88
• 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：

  12-chloro-1,1-diethoxy-dodec-2-yne 在 镍 氢气 、 草酸 作用下， 生成 12-chloro-dodecanal
  参考文献：
  名称：

  Epsztein,R. et al., Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences, 1961, vol. 252, p. 1803 - 1805

  摘要：

  DOI：
• 作为产物：
  描述：

  11-氯-1-十一碳炔 、 原甲酸三乙酯 在 锌 作用下， 生成 12-chloro-1,1-diethoxy-dodec-2-yne
  参考文献：
  名称：

  Epsztein,R. et al., Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences, 1961, vol. 252, p. 1803 - 1805

  摘要：

  DOI：

文献信息

• OMEGA-HALO-2-ALKYNAL, METHOD FOR PRODUCING SAME, AND METHOD FOR PRODUCING CONJUGATED Z-ALKEN-YN-YL ACETATE USING SAME
  申请人：Shin-Etsu Chemical Co., Ltd.

  公开号：US20140309452A1

  公开（公告）日：2014-10-16

  Provided is a method for industrially producing a conjugated Z-alken-yn-yl acetate such as Z-13-hexadecen-11-yn-yl acetate which is a sex pheromone component of a pine processionary moth, and an intermediate for the conjugated Z-alken-yn-yl acetate under mild conditions at a high yield. More specifically, provided is a method for producing a conjugated Z-alken-yn-yl acetate (5) comprising the steps of: reacting an ω-halo-2-alkynal (1) with an alkylidene triphenylphosphorane (3) through a Wittig reaction to obtain a conjugated Z-alken-yn-yl halide (4), and acetoxylating the conjugated Z-alken-yn-yl halide (4) into a conjugated Z-alken-yn-yl acetate (5).

  提供了一种工业生产共轭的Z-烯炔基乙酸酯的方法，例如Z-13-十六烯-11-炔基乙酸酯，它是松毛虫的性信息素成分，并在温和条件下高产率地获得共轭的Z-烯炔基乙酸酯的中间体。更具体地说，提供了一种生产共轭的Z-烯炔基乙酸酯（5）的方法，包括以下步骤：通过Wittig反应将ω-卤代-2-炔醛（1）与烷基三苯基膦烯（3）反应，以获得共轭的Z-烯炔基卤化物（4），并将共轭的Z-烯炔基卤化物（4）乙酰化为共轭的Z-烯炔基乙酸酯（5）。
• METHOD FOR PRODUCING AN OMEGA-HALO-2-ALKYNAL
  申请人：Shin-Etsu Chemical Co., Ltd.

  公开号：US20160107969A1

  公开（公告）日：2016-04-21

  Provided is a method for industrially producing a conjugated Z-alken-yn-yl acetate such as Z-13-hexadecen-11-yn-yl acetate which is a sex pheromone component of a pine processionary moth, and an intermediate for the conjugated Z-alken-yn-yl acetate under mild conditions at a high yield. More specifically, provided is a method for producing a conjugated Z-alken-yn-yl acetate (5) comprising the steps of: reacting an ω-halo-2-alkynal (1) with an alkylidene triphenylphosphorane (3) through a Wittig reaction to obtain a conjugated Z-alken-yn-yl halide (4), and acetoxylating the conjugated Z-alken-yn-yl halide (4) into a conjugated Z-alken-yn-yl acetate (5).

  提供了一种工业生产共轭Z-烯炔-醇酸酯的方法，例如Z-13-十六烯-11-炔-醋酸酯，它是松毛虫的性信息素成分，并在温和条件下高产率地制备共轭Z-烯炔-醇酸酯的中间体。更具体地，提供了一种制备共轭Z-烯炔-醇酸酯（5）的方法，包括以下步骤：通过Wittig反应，将ω-卤代-2-炔醛（1）与三苯基膦亚甲基（3）反应，得到共轭Z-烯炔-醇酸酯（4），并将共轭Z-烯炔-醇酸酯（4）乙酰化为共轭Z-烯炔-醇酸酯（5）。
• METHOD FOR PRODUCING A CONJUGATED Z-ALKEN-YN-YL ACETATE
  申请人：Shin-Etsu Chemical Co., Ltd.

  公开号：US20160107978A1

  公开（公告）日：2016-04-21

  Provided is a method for industrially producing a conjugated Z-alken-yn-yl acetate such as Z-13-hexadecen-11-yn-yl acetate which is a sex pheromone component of a pine processionary moth, and an intermediate for the conjugated Z-alken-yn-yl acetate under mild conditions at a high yield. More specifically, provided is a method for producing a conjugated Z-alken-yn-yl acetate (5) comprising the steps of: reacting an ω-halo-2-alkynal (1) with an alkylidene triphenylphosphorane (3) through a Wittig reaction to obtain a conjugated Z-alken-yn-yl halide (4), and acetoxylating the conjugated Z-alken-yn-yl halide (4) into a conjugated Z-alken-yn-yl acetate (5).

  提供了一种工业生产共轭Z-烯炔基乙酸酯的方法，例如Z-13-十六烯-11-炔基乙酸酯，它是松毛虫的性信息素成分，以及在温和条件下高产率下制备共轭Z-烯炔基乙酸酯的中间体。更具体地说，提供了一种生产共轭Z-烯炔基乙酸酯（5）的方法，包括以下步骤：通过Wittig反应将ω-卤代-2-炔醛（1）与烷基三苯基膦（3）反应，以获得共轭Z-烯炔基卤化物（4），并将共轭Z-烯炔基卤化物（4）乙酰化为共轭Z-烯炔基乙酸酯（5）。
• A method for the preparation of a gamma-substituted (E)-2-alken-1-AL
  申请人：Shin-Etsu Chemical Co., Ltd.

  公开号：EP0282940A2

  公开（公告）日：1988-09-21

  An efficient method is disclosed for the preparation of an ω-­substituted (E)-2-alken-1-al, e.g., 12-chloro-(E)-2-dodecen-1-al in three steps of reactions. The starting compound is an ω-substituted 1-alkynyl magnesium halide which is reacted with trimethyl or triethyl orthoformate to give an ω-substituted 1,1-dialkoxy-2-al­kyne followed by a partial hydrogenation of the triple bond and then hydrolysis or, alternatively, followed by the hydrolysis reac­tion and then partial hydrogenation of the triple bond.

  本发明公开了一种通过三步反应制备ω-取代的(E)-2-烯-1-醛，例如 12-氯-(E)-2-十二烯-1-醛的有效方法。起始化合物为ω-取代的 1-炔基卤化镁，与原甲酸三甲酯或原甲酸三乙酯反应，得到ω-取代的 1,1-二烷氧基-2-炔，然后进行三键的部分氢化反应，再进行水解，或者先进行水解反应，再进行三键的部分氢化反应。
• Omega-halo-2-alkynal, method for producing same, and method for producing conjugated Z-alken-yn-yl acetate using same
  申请人：SHIN-ETSU CHEMICAL CO., LTD

  公开号：EP2789602A1

  公开（公告）日：2014-10-15

  Provided is a method for industrially producing a conjugated Z-alken-yn-yl acetate such as Z-13-hexadecen-11-yn-yl acetate which is a sex pheromone component of a pine processionary moth, and an intermediate for the conjugated Z-alken-yn-yl acetate under mild conditions at a high yield. More specifically, provided is a method for producing a conjugated Z-alken-yn-yl acetate (5) comprising the steps of: reacting an ω-halo-2-alkynal (1) with an alkylidene triphenylphosphorane (3) through a Wittig reaction to obtain a conjugated Z-alken-yn-yl halide (4), and acetoxylating the conjugated Z-alken-yn-yl halide (4) into a conjugated Z-alken-yn-yl acetate (5).

  本发明提供了一种在温和条件下工业化生产共轭 Z-烯炔基乙酸酯如 Z-13-hexadecen-11-炔基乙酸酯的方法，Z-烯炔基乙酸酯是松树游蛾的一种性信息素成分，本发明还提供了一种高产率的共轭 Z-烯炔基乙酸酯的中间体。更具体地说，提供了一种生产共轭 Z-烯炔基乙酸酯（5）的方法，包括以下步骤：通过 Wittig 反应使ω-卤代-2-炔醛（1）与亚烷基三苯基膦（3）反应，得到共轭 Z-烯炔基卤化物（4），并将共轭 Z-烯炔基卤化物（4）乙酰氧基化成共轭 Z-烯炔基乙酸酯（5）。