5-[5-(2-methyl-[1,3]dioxolan-2-yl)-thiophen-2-yl]-nicotinonitrile | 1393709-40-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 5-[5-(2-methyl-[1,3]dioxolan-2-yl)-thiophen-2-yl]-nicotinonitrile
• 英文别名: 5-[5-(2-Methyl-1,3-dioxolan-2-yl)thiophen-2-yl]pyridine-3-carbonitrile；5-[5-(2-methyl-1,3-dioxolan-2-yl)thiophen-2-yl]pyridine-3-carbonitrile
• CAS: 1393709-40-4
• 化学式: C₁₄H₁₂N₂O₂S
• 分子量: 272.327
• InChiKey: ARPDYNHFOPQAKD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  83.4
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  5-溴烟腈 、 2-乙酰基噻吩乙烯缩醛 在 PdCl(C₃H₅)(dppb) 、 potassium acetate 作用下， 以 N,N-二甲基乙酰胺 为溶剂， 反应 20.0h， 以91%的产率得到5-[5-(2-methyl-[1,3]dioxolan-2-yl)-thiophen-2-yl]-nicotinonitrile
  参考文献：
  名称：

  Palladium-catalysed direct arylation of heteroaromatics with functionalised bromopyridines

  摘要：

  The regioselective 5-arylation of a variety of heteroaromatics with functionalised pyridyl bromides using palladium catalyst gives a simple access to functionalised heteroarylated pyridines. The target products were obtained in moderate to good yields using only 1 mol % PdCl(C3H5)(dppb) as the catalyst. Substituents, such as fluoro, acetyl, nitrile, nitro, methoxy or amino on the pyridyl bromide are tolerated. However, the nature of the substituents has an important influence on the yields. Electron-withdrawing substituent favours the reaction; whereas electron-donating are unfavourable. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2012.06.034

文献信息

• Palladium-catalysed direct arylation of heteroaromatics with functionalised bromopyridines
  作者：Souhila Bensaid、Henri Doucet

  DOI：10.1016/j.tet.2012.06.034

  日期：2012.9

  The regioselective 5-arylation of a variety of heteroaromatics with functionalised pyridyl bromides using palladium catalyst gives a simple access to functionalised heteroarylated pyridines. The target products were obtained in moderate to good yields using only 1 mol % PdCl(C3H5)(dppb) as the catalyst. Substituents, such as fluoro, acetyl, nitrile, nitro, methoxy or amino on the pyridyl bromide are tolerated. However, the nature of the substituents has an important influence on the yields. Electron-withdrawing substituent favours the reaction; whereas electron-donating are unfavourable. (C) 2012 Elsevier Ltd. All rights reserved.