4-Ethyl-2-((E)-styryl)-pyridine

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 4-Ethyl-2-((E)-styryl)-pyridine
• 英文别名: 4-Ethyl-2-[(E)-2-phenylvinyl]pyridine；4-ethyl-2-[(E)-2-phenylethenyl]pyridine
• 化学式: C₁₅H₁₅N
• 分子量: 209.291
• InChiKey: FGHMUQFLTSPJQI-CMDGGOBGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.13
• 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：

  4-乙基吡啶 、 苯基乙炔基三甲基硅烷 在 sodium hexaflorophosphate 、 二(三苯基膦)环戊二烯基氯化钌(II) 作用下， 反应 11.0h， 以66%的产率得到4-Ethyl-2-((E)-styryl)-pyridine
  参考文献：
  名称：

  Ruthenium-Mediated Regio- and Stereoselective Alkenylation of Pyridine

  摘要：

  A novel alkenylation reaction of pyridine is developed. Heating a cationic ruthenium vinylidene complex [CpRu(=C=CHR)(PPh(3))(2)]PF(6) in pyridine at 100-125 degrees C for 24 h affords (E)-2-alkenylpyridine. Initially, pyridine coordinates to ruthenium by displacement of one of the phosphine ligands. Then, [2 + 2] heterocycloaddition occurs to form a four-membered ruthenacyclic complex. Deprotonation of the beta-hydrogen affords a neutral pi-azaallyl complex. Protonolysis furnishes the product. As a result, a vinylidene group is inserted into the alpha C-H bond of pyridine. The alkenylation reaction is made catalytic in ruthenium by the use of (alkyn-1-yl)silane as the vinylidene source. Treatment of (alkyn-1-yl)trimethylsilane with pyridine in the presence of a cationic ruthenium complex [CpRu(PPh(3))(2)]PF(6) affords the corresponding (E)-2-alkenylpyridine in good yield in a regio- and stereoselective manner.

  DOI：

  10.1021/ja029829z

文献信息

• Ruthenium-Mediated Regio- and Stereoselective Alkenylation of Pyridine
  作者：Masahiro Murakami、Seiji Hori

  DOI：10.1021/ja029829z

  日期：2003.4.1

  A novel alkenylation reaction of pyridine is developed. Heating a cationic ruthenium vinylidene complex [CpRu(=C=CHR)(PPh(3))(2)]PF(6) in pyridine at 100-125 degrees C for 24 h affords (E)-2-alkenylpyridine. Initially, pyridine coordinates to ruthenium by displacement of one of the phosphine ligands. Then, [2 + 2] heterocycloaddition occurs to form a four-membered ruthenacyclic complex. Deprotonation of the beta-hydrogen affords a neutral pi-azaallyl complex. Protonolysis furnishes the product. As a result, a vinylidene group is inserted into the alpha C-H bond of pyridine. The alkenylation reaction is made catalytic in ruthenium by the use of (alkyn-1-yl)silane as the vinylidene source. Treatment of (alkyn-1-yl)trimethylsilane with pyridine in the presence of a cationic ruthenium complex [CpRu(PPh(3))(2)]PF(6) affords the corresponding (E)-2-alkenylpyridine in good yield in a regio- and stereoselective manner.