(3E,5E)-ethyl 3-((E)-styryl)hepta-3,5-dienoate | 1311158-79-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (3E,5E)-ethyl 3-((E)-styryl)hepta-3,5-dienoate
• 英文别名: ethyl (3E,5E)-3-[(E)-2-phenylethenyl]hepta-3,5-dienoate
• CAS: 1311158-79-8
• 化学式: C₁₇H₂₀O₂
• 分子量: 256.345
• InChiKey: RJEBDLFKVWHIBV-MVWHDUQSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  19
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  巴豆醛 、 ethyl 5-phenylpent-2-ynoate 在 1,3,5-三氮杂-7-磷杂金刚烷 作用下， 以 1,4-二氧六环 为溶剂， 反应 16.0h， 以42%的产率得到(3E,5E)-ethyl 3-((E)-styryl)hepta-3,5-dienoate
  参考文献：
  名称：

  β-Olefination of 2-Alkynoates Leading to Trisubstituted 1,3-Dienes

  摘要：

  A phosphine-mediated olefination of 2-alkynoates with aldehydes forming 1,3-dienes with high E-selectivity and up to 88% yield is described. Reaction conditions are optimized and reactions are demonstrated for,various aryl, alkyl, and alkenyl aldehydes and for ethyl 2-alkynoates with different substituents in the delta-position. Proof of concept is shown for the generation of a beta,gamma-unsaturated lactone by intramolecular olefination, and furthermore the use of the generated 1,3-dienes in the Diels-Alder reaction has been demonstrated.

  DOI：

  10.1021/ol2011677

文献信息

• β-Olefination of 2-Alkynoates Leading to Trisubstituted 1,3-Dienes
  作者：Mathias J. Jacobsen、Erik Daa Funder、Jacob R. Cramer、Kurt V. Gothelf

  DOI：10.1021/ol2011677

  日期：2011.7.1

  A phosphine-mediated olefination of 2-alkynoates with aldehydes forming 1,3-dienes with high E-selectivity and up to 88% yield is described. Reaction conditions are optimized and reactions are demonstrated for,various aryl, alkyl, and alkenyl aldehydes and for ethyl 2-alkynoates with different substituents in the delta-position. Proof of concept is shown for the generation of a beta,gamma-unsaturated lactone by intramolecular olefination, and furthermore the use of the generated 1,3-dienes in the Diels-Alder reaction has been demonstrated.