3,3',5,5'-tetra(p-N,N-dimethylaminophenylethynyl)biphenyl | 1145777-03-2

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二芳基庚烷
• 英文名称: 3,3',5,5'-tetra(p-N,N-dimethylaminophenylethynyl)biphenyl
• 英文别名: 4-[2-[3-[3,5-bis[2-[4-(dimethylamino)phenyl]ethynyl]phenyl]-5-[2-[4-(dimethylamino)phenyl]ethynyl]phenyl]ethynyl]-N,N-dimethylaniline
• CAS: 1145777-03-2
• 化学式: C₅₂H₄₆N₄
• 分子量: 726.964
• InChiKey: NOVLWNLOOYVJIB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  12.1
• 重原子数：
  56
• 可旋转键数：
  13
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  13
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  1-bromo-3,5-di(p-N,N-dimethylaminophenylethynyl)benzene 在 bis(triphenylphosphine)nickel(II) chloride 、 四丁基碘化铵 、 锌 作用下， 以 四氢呋喃 为溶剂， 反应 12.0h， 以65%的产率得到3,3',5,5'-tetra(p-N,N-dimethylaminophenylethynyl)biphenyl
  参考文献：
  名称：

  Efficient synthesis of 3,3′,5,5′-tetra(p-X-phenylethynyl)biphenyl (X: NMe2; OMe) by homocoupling of 1-bromo-3,5-di(p-X-phenylethynyl)benzene or by heterocoupling of 3,3′,5,5′-tetraethynylbiphenyl with p-X-phenylbromobenzene with nickel or palladium complexes, respectively

  摘要：

  The conjugated 3,3',5,5'-tetra(p-X-phenylethynyl)biphenyl derivatives were efficiently obtained by homocoupling of 1-bromo-3,5-di(p-X-phenylethynyl)benzene mediated by zero-valent nickel complexes. The 1-bromo 3,5-di(p-X-phenylethynyl)benzene was previously prepared by heterocoupling between 1-bromo-3,5-di(ethynyl)benzene and p-X- iodobenzene (X: NMe2; OMe) catalysed by the palladium/copper system in good yield. The necessary 1-bromo-3,5-di(ethynyl)benzene was obtained by heterocoupling between 1,3,5-tribromobenzene and 2-methyl-3-butyn-2-ol catalysed by palladium and successive treatment with sodium hydroxide in dry toluene, in good yield.The same 3,3',5,5'-tetra(p-X-phenylethynyl)biphenyl (X: NMe2; OMe) derivatives were alternatively synthesised in highest yield by heterocoupling between 3,3',5,5'-tetra(ethynyl)biphenyl and p-X-bromobenzene (X: NMe2; OMe) catalysed by palladium in excellent yields. Previously, 3,3',5,5'-tetra(ethynyl)biphenyl was obtained in practically quantitative yield by homocoupling of 1-bromo-3,5-di-[4-(2-methyl-3-butyn-2-ol)] benzene mediated by the zero-valent nickel complex to the 3,3',5,5'-tetra[di-[4-(2-methyl-3-butyn-2-ol)] followed the treatment with sodium hydroxide. (C) 2009 Published by Elsevier Ltd.

  DOI：

  10.1016/j.tet.2009.01.036

文献信息

• Efficient synthesis of 3,3′,5,5′-tetra(p-X-phenylethynyl)biphenyl (X: NMe2; OMe) by homocoupling of 1-bromo-3,5-di(p-X-phenylethynyl)benzene or by heterocoupling of 3,3′,5,5′-tetraethynylbiphenyl with p-X-phenylbromobenzene with nickel or palladium complexes, respectively
  作者：J. Gonzalo Rodríguez、Teresa Laparra

  DOI：10.1016/j.tet.2009.01.036

  日期：2009.3

  The conjugated 3,3',5,5'-tetra(p-X-phenylethynyl)biphenyl derivatives were efficiently obtained by homocoupling of 1-bromo-3,5-di(p-X-phenylethynyl)benzene mediated by zero-valent nickel complexes. The 1-bromo 3,5-di(p-X-phenylethynyl)benzene was previously prepared by heterocoupling between 1-bromo-3,5-di(ethynyl)benzene and p-X- iodobenzene (X: NMe2; OMe) catalysed by the palladium/copper system in good yield. The necessary 1-bromo-3,5-di(ethynyl)benzene was obtained by heterocoupling between 1,3,5-tribromobenzene and 2-methyl-3-butyn-2-ol catalysed by palladium and successive treatment with sodium hydroxide in dry toluene, in good yield.The same 3,3',5,5'-tetra(p-X-phenylethynyl)biphenyl (X: NMe2; OMe) derivatives were alternatively synthesised in highest yield by heterocoupling between 3,3',5,5'-tetra(ethynyl)biphenyl and p-X-bromobenzene (X: NMe2; OMe) catalysed by palladium in excellent yields. Previously, 3,3',5,5'-tetra(ethynyl)biphenyl was obtained in practically quantitative yield by homocoupling of 1-bromo-3,5-di-[4-(2-methyl-3-butyn-2-ol)] benzene mediated by the zero-valent nickel complex to the 3,3',5,5'-tetra[di-[4-(2-methyl-3-butyn-2-ol)] followed the treatment with sodium hydroxide. (C) 2009 Published by Elsevier Ltd.