(E)-(3-(3-oxo-1-phenylbut-1-en-2-yl)indolizin-2-yl)triphenylphosphonium tetrafluoroborate | 1443430-74-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 咪唑并吡啶类
• 英文名称: (E)-(3-(3-oxo-1-phenylbut-1-en-2-yl)indolizin-2-yl)triphenylphosphonium tetrafluoroborate
• CAS: 1443430-74-7
• 化学式: BF₄*C₃₆H₂₉NOP
• 分子量: 609.411
• InChiKey: KGZBDLZDPYPILL-NOEFFRSSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.99
• 重原子数：
  44.0
• 可旋转键数：
  7.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.03
• 拓扑面积：
  21.48
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为产物：
  描述：

  [Ru(CHC(PPh₃)CH(2-Py))Cl₂PPh₃]BF₄ 、 4-苯基-3-丁炔-2-酮 在 tetrafluoroboric acid 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 以83%的产率得到(E)-(3-(3-oxo-1-phenylbut-1-en-2-yl)indolizin-2-yl)triphenylphosphonium tetrafluoroborate
  参考文献：
  名称：

  Mechanistic Study of Indolizine Heterocycle Formation by Ruthenium(II)-Assisted Three-Component Cross-Coupling/Cyclization

  摘要：

  In the presence of the acid HBF4, 3-alkenyl-2-phosphonium indolizines 3a-c can be produced respectively by adding PhC CCOCH3 (2a), CH3OCOC CCOOCH3 (2b), and CH3CH2C CCOCH3 (2c) to a mixture of ruthenium complex RuCl2(PPh3)(3) and the propargyl alcohol (2-Py)CH(OH)C CH (1). We carefully investigated the mechanism of this reaction by means of structurally characterizing two key intermediates, ruthenium vinyl (4) and ruthenium carbene (5), and by deuterium-labeling experiments. A plausible mechanism is proposed, which involves addition of a proton to an alkyne carbon and the insertion of an alkyne into the C alpha bond of an alkenylcarbene group, followed by an alpha-H elimination and reductive elimination.

  DOI：

  10.1021/om400372w