(2E,4E)-ethyl 5-cyanopenta-2,4-dienoate | 1231182-89-0

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (2E,4E)-ethyl 5-cyanopenta-2,4-dienoate
• 英文别名: ethyl (2E,4E)-5-cyanopenta-2,4-dienoate
• CAS: 1231182-89-0
• 化学式: C₈H₉NO₂
• 分子量: 151.165
• InChiKey: JJLGBJYSMPBOHA-GGWOSOGESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  11
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  50.1
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  在 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 3.0h， 以46 mg的产率得到(2E,4E)-ethyl 5-cyanopenta-2,4-dienoate
  参考文献：
  名称：

  An Efficient Transformation from Benzyl or Allyl Halides to Aryl and Alkenyl Nitriles

  摘要：

  A novel approach to aryl or alkenyl nitriles from benzyl and allyl halides has been developed. A tandem TBAB-catalyzed substitution and the subsequent novel oxidative rearrangement are involved in this transformation. To the best of our knowledge, this is the first transformation from allyl halides to alkenyl nitriles. The broad reaction scope and the mild conditions may make these methods of use in organic synthesis.

  DOI：

  10.1021/ol101094u

文献信息

• Ruthenium-Catalyzed Oxidative Cross-Coupling Reaction of Activated Olefins with Vinyl Boronates for the Synthesis of (<i>E</i>,<i>E</i>)-1,3-Dienes
  作者：Dattatraya H. Dethe、Nagabhushana C. Beeralingappa、Amar Uike

  DOI：10.1021/acs.joc.0c02823

  日期：2021.2.19

  An oxidative cross-coupling reaction between activated olefins and vinyl boronate derivatives has been developed for the highly stereoselective construction of synthetically useful (E,E)-1,3-dienes. The highlight of this reaction is that exclusive stereoselectivity (only E,E-isomer) was achieved from a base-free, ligand-free, and mild catalytic condition with a less expensive [RuCl2(p-cymene)]2 catalyst

  已经开发出活化烯烃和乙烯基硼酸酯衍生物之间的氧化交叉偶联反应，以用于合成有用的（E，E）-1，3-二烯的高度立体选择性的结构。该反应的亮点在于，使用便宜的[RuCl 2（p- Cymene）] 2催化剂，可从无碱，无配体和温和的催化条件下获得独特的立体选择性（仅E，E-异构体）。
• An Efficient Transformation from Benzyl or Allyl Halides to Aryl and Alkenyl Nitriles
  作者：Wang Zhou、Jiaojiao Xu、Liangren Zhang、Ning Jiao

  DOI：10.1021/ol101094u

  日期：2010.6.18

  A novel approach to aryl or alkenyl nitriles from benzyl and allyl halides has been developed. A tandem TBAB-catalyzed substitution and the subsequent novel oxidative rearrangement are involved in this transformation. To the best of our knowledge, this is the first transformation from allyl halides to alkenyl nitriles. The broad reaction scope and the mild conditions may make these methods of use in organic synthesis.