(E)-3-(2-triethylsilanylvinyl)quinoline

• 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: (E)-3-(2-triethylsilanylvinyl)quinoline
• 英文别名: triethyl-[(E)-2-quinolin-3-ylethenyl]silane
• 化学式: C₁₇H₂₃NSi
• 分子量: 269.462
• InChiKey: VKOYOMHOLNVWTG-VAWYXSNFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  12.9
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  3-溴喹啉 、 三乙基乙烯基硅烷 在 bis(η3-allyl-μ-chloropalladium(II)) sodium acetate 、 顺式,顺式,顺式-1,2,3,4-四[(二苯基膦)甲基]环戊烷 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 20.0h， 以85%的产率得到(E)-3-(2-triethylsilanylvinyl)quinoline
  参考文献：
  名称：

  Selective synthesis of (E)-triethyl(2-arylethenyl)silane derivatives by reaction of aryl bromides with triethyl vinylsilane catalysed by a palladium–tetraphosphine complex

  摘要：

  Cis, cis, cis-1,2,3,4-tetrakis(diphenylphosphinomethyl)cyclopentane/0.5[PdCI(C3H5)](2) system catalyses the Heck reaction of vinylsilane derivatives with a range of aryl bromides with high ratio substrate/catalyst in good yields. The formation of mixtures of styrene, (E)-triethyl(2-arylethenyl)sitane and triethyl(1-arylethenyl)silane derivatives was observed in some cases. Very high selectivities (up to 100%) in favour of the formation of (E)-triethyl(2-arylethenyl)silane derivatives were obtained in the presence of sodium acetate as base. With other bases such as potassium carbonate, the formation of large amounts of styrene derivatives was observed. The reaction tolerates several functions such as fluoro, trifluoromethyl, methoxy, dimethylamino, acetyl, formyl, benzoyl, carboxylate, nitro or nitrile. Moreover, turnover numbers up to 10,000 can be obtained for this reaction. (c) 2005 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jorganchem.2005.05.014