3-quinolinyltriphenylphosphonium iodide | 1203646-09-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 3-quinolinyltriphenylphosphonium iodide
• CAS: 1203646-09-6
• 化学式: C₂₇H₂₁NP*I
• 分子量: 517.349
• InChiKey: PSWQGLQLOQXAME-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  1.86
• 重原子数：
  30.0
• 可旋转键数：
  4.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  12.89
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  3-quinolinyltriphenylphosphonium iodide 在 乙醇 、 三乙胺 作用下， 反应 1.0h， 以87%的产率得到喹啉
  参考文献：
  名称：

  Preparation and Reaction of Quinolinyl (or Pyridinyl)phosphonium Salts with Base and Pivalaldehyde

  摘要：

  alpha- and gamma-Heteroaryltriphenylphosphonium iodides were prepared by reaction of the corresponding heteroaryl iodides with triphenylphosphine. Reaction of beta-heteroaryl iodides with triphenylphosphine in the presence of a palladium catalyst gave beta-heteroaryltriphenylphosphonium iodides. Elimination of the heteroaryl group was achieved by treating the heteroaryltriphenylphosphonium iodides with a base. Further, the heteroaryl group was trapped with pivalaldehyde to introduce a pivaloyl substituent onto the heteroaromatic ring.

  DOI：

  10.3987/com-11-12154
• 作为产物：
  描述：

  3-碘喹啉 、 三苯基膦 在 tris-(dibenzylideneacetone)dipalladium(0) 作用下， 以 5,5-dimethyl-1,3-cyclohexadiene 为溶剂， 反应 16.0h， 以95%的产率得到3-quinolinyltriphenylphosphonium iodide
  参考文献：
  名称：

  Chemistry of Heteroaryltriphenylphosphonium Iodides: Preparation from Iodoheteroaromatics and Elimination of the Phosphonium Iodide Group Using Basic Solvents

  摘要：

  alpha- and gamma-lodoheteroaromatics were found to react with triphenylphosphine to give heteroaromatictriphenylphosphonium iodides in excellent yields. beta-lodoheteroaromatics, which are less reactive with triphenylphosphine compared to alpha- or gamma-compounds, were converted into the corresponding phosphonium iodides using palladium catalysts. Treatment of heteroaromatictriphenylphosphonium iodides resulted in the elimination of the phosphonium iodide group using basic solvents such as aqueous sodium hydroxide or ethanol - triethylamine.

  DOI：

  10.3987/com-09-11799