ethyl 4-[(E)-styryl]quinoline-1(4H)-carboxylate | 1116008-65-1

• 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: ethyl 4-[(E)-styryl]quinoline-1(4H)-carboxylate
• 英文别名: ethyl 4-[(E)-2-phenylethenyl]-4H-quinoline-1-carboxylate
• CAS: 1116008-65-1
• 化学式: C₂₀H₁₉NO₂
• 分子量: 305.376
• InChiKey: SCXAHTVRUKZKJX-OUKQBFOZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  喹啉 、 (E)-styrylzirconocene chloride 、 氯甲酸乙酯 以 硝基甲烷 为溶剂， 反应 14.0h， 以82%的产率得到ethyl 2-[(E)-styryl]quinoline-1(2H)-carboxylate
  参考文献：
  名称：

  Reissert-like Alkenylation of Azaaromatic Compounds with Alkenylzirconocene Chloride Complexes

  摘要：

  Reissert-like alkenylation of azaaromatic compounds by the use of alkenylzirconocene chloride as a nucleophile was carried out in the presence of a stoichiometric amount of ClCO2Et. The regioselectivity of the nucleophilic attack depends on reacting heterocycles, solvent, and the presence of copper catalyst. Thus, the reaction of quinoline derivatives with alkenylzirconocene chloride in MeNO2 proceeded in a preferential 1,2-addition manner to give N-ethoxycarbonyl-2-alkenyl-1,2-dihydroquinolines, and the reaction of pyridine in CH2Cl2 under Cu(I)-catalyzed conditions proceeded in a 1,4-addition manner to give N-ethoxycarbonyl-4-alkenyl-1,4-dihydropyridine. The alkenylation of 3,4-dihydroisoquinoline with alkenylzirconocene chloride was also carried out in an enantioselective manner under Cu(I)/chiral Box-catalyzed conditions to give alkenylated tetrahydroisoquinoline compound (75%ee).

  DOI：

  10.3987/com-12-s(n)7

文献信息

• Reissert-like Alkenylation of Azaaromatic Compounds with Alkenylzirconocene Chloride Complexes
  作者：Akio Saito、Yuji Hanzawa、Kohei Sudo、Koichi Iimura、Miki Hayashi

  DOI：10.3987/com-12-s(n)7

  日期：——

  Reissert-like alkenylation of azaaromatic compounds by the use of alkenylzirconocene chloride as a nucleophile was carried out in the presence of a stoichiometric amount of ClCO2Et. The regioselectivity of the nucleophilic attack depends on reacting heterocycles, solvent, and the presence of copper catalyst. Thus, the reaction of quinoline derivatives with alkenylzirconocene chloride in MeNO2 proceeded in a preferential 1,2-addition manner to give N-ethoxycarbonyl-2-alkenyl-1,2-dihydroquinolines, and the reaction of pyridine in CH2Cl2 under Cu(I)-catalyzed conditions proceeded in a 1,4-addition manner to give N-ethoxycarbonyl-4-alkenyl-1,4-dihydropyridine. The alkenylation of 3,4-dihydroisoquinoline with alkenylzirconocene chloride was also carried out in an enantioselective manner under Cu(I)/chiral Box-catalyzed conditions to give alkenylated tetrahydroisoquinoline compound (75%ee).