12-chloro-2-dodecynal | 100251-32-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 12-chloro-2-dodecynal
• 英文别名: 12-chloro-dodec-2-ynal；12-Chlorododec-2-ynal；12-chlorododec-2-ynal
• CAS: 100251-32-9
• 化学式: C₁₂H₁₉ClO
• 分子量: 214.735
• InChiKey: IGLBWKSPQMCDMY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  14
• 可旋转键数：
  8
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  11-氯-1-十一碳炔 在 锌 草酸 作用下， 生成 12-chloro-2-dodecynal
  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）。
• 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）。
• Omega-halo-2-alkynal, method for producing the same, and method for producing conjugated Z-alken-yn-yl acetate using the same
  申请人：SHIN-ETSU CHEMICAL CO., LTD

  公开号：EP2789602B1

  公开（公告）日：2017-12-27