2-oxoethyl 5-phenylpent-2-ynoate | 1311158-71-0

• 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: 2-oxoethyl 5-phenylpent-2-ynoate
• CAS: 1311158-71-0
• 化学式: C₁₃H₁₂O₃
• 分子量: 216.236
• InChiKey: NMBGCDZOEDURAW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  16
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-oxoethyl 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 19.0h， 以8%的产率得到(E)-4-styryl-3,6-dihydro-2H-pyran-2-one
  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
• 作为产物：
  描述：

  2-hydroxyethyl 5-phenylpent-2-ynoate 在 戴斯-马丁氧化剂 作用下， 以 二氯甲烷 为溶剂， 反应 6.0h， 以50%的产率得到2-oxoethyl 5-phenylpent-2-ynoate
  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