(1E,4E)-1-[4-(dimethylamino)phenyl]-5-(5-fluoropyridin-2-yl)penta-1,4-dien-3-one | 1424279-01-5

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: (1E,4E)-1-[4-(dimethylamino)phenyl]-5-(5-fluoropyridin-2-yl)penta-1,4-dien-3-one
• CAS: 1424279-01-5
• 化学式: C₁₈H₁₇FN₂O
• 分子量: 296.344
• InChiKey: WXXREKXHXSCRHJ-QAZZFAKDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  33.2
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  2-溴-5-氟吡啶 、 (E)-1-[4-(dimethylamino)phenyl]pent-1-en-4-yn-3-ol 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 三乙胺 、 三苯基膦 作用下， 以 1,4-二氧六环 为溶剂， 反应 0.75h， 以52%的产率得到(1E,4E)-1-[4-(dimethylamino)phenyl]-5-(5-fluoropyridin-2-yl)penta-1,4-dien-3-one
  参考文献：
  名称：

  Versatile Synthesis of Dissymmetric Diarylideneacetones via a Palladium-Catalyzed­ Coupling–Isomerization Reaction

  摘要：

  As a twofold Michael system, the diarylideneacetone core is of particular interest in organic synthesis and for therapeutic applications. To overcome the drawbacks of the classical Claisen-Schmidt protocol, a new methodology for the synthesis of dissymmetric (hetero)diarylideneacetones has been developed. Conditions were optimized with a Box-Behnken design of experiment. The milder reaction conditions allow the efficient preparation of fluorinated, or heteroaromatic, dissymmetric diarylideneacetones which cannot be obtained through the classical Claisen-Schmidt protocol.

  DOI：

  10.1055/s-0032-1316811

文献信息

• Versatile Synthesis of Dissymmetric Diarylideneacetones via a Palladium-Catalyzed­ Coupling–Isomerization Reaction
  作者：Thomas Müller、Thibault Gendron、Elisabeth Davioud-Charvet

  DOI：10.1055/s-0032-1316811

  日期：——

  As a twofold Michael system, the diarylideneacetone core is of particular interest in organic synthesis and for therapeutic applications. To overcome the drawbacks of the classical Claisen-Schmidt protocol, a new methodology for the synthesis of dissymmetric (hetero)diarylideneacetones has been developed. Conditions were optimized with a Box-Behnken design of experiment. The milder reaction conditions allow the efficient preparation of fluorinated, or heteroaromatic, dissymmetric diarylideneacetones which cannot be obtained through the classical Claisen-Schmidt protocol.