2,2'-Bipyridine-5-N-(6-hydroxyhexyl)carboxamide | 161954-78-5

• 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: 2,2'-Bipyridine-5-N-(6-hydroxyhexyl)carboxamide
• 英文别名: N-(6-hydroxyhexyl)-6-pyridin-2-ylpyridine-3-carboxamide
• CAS: 161954-78-5
• 化学式: C₁₇H₂₁N₃O₂
• 分子量: 299.373
• InChiKey: VXPLDCJHHJRATD-UHFFFAOYSA-N

物化性质

• 沸点：
  534.1±50.0 °C(predicted)
• 密度：
  1.144±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  22
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  75.1
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2,2'-Bipyridine-5-N-(6-hydroxyhexyl)carboxamide 、 甲基丙烯酰氯 在 吡啶 作用下， 以 氯仿 为溶剂， 反应 16.0h， 以64%的产率得到2,2'-Bipyridine-5-N-(6-(methacryloxy)hexyl)carboxamide
  参考文献：
  名称：

  Reduction of Nicotinamides, Flavins, and Manganese Porphyrins by Formate, Catalyzed by Membrane-Bound Rhodium Complexes

  摘要：

  Two polymerizable cyclopentadienyl-2,2'-bipyridinerhodium complexes and one amphiphilic rhodium complex have been synthesized and incorporated into the bilayers of vesicles formed from a polymerizable ammonium surfactant. Incorporation was achieved by chemical linkage (via a copolymerization reaction) or by physical absorption. The complexes are located at different positions in the bilayer, viz, in the hydrophobic interior or at the aqueous interface. The anchored rhodium complexes efficiently catalyze the reduction of both two-electron substrates (e.g., nicotinamides and flavin) and one-electron substrates (e.g., manganese(III) porphyrins) by sodium formate. Kinetic studies indicate that the rate-limiting step of the reaction is the reduction of the rhodium center by formate, leading to a rhodium(III) hydride or a rhodium(I) species. The three complexes showed different catalytic activities. Cyclic voltammetry and UV-vis measurements revealed that their reduction potentials ([Rh(III)](2+) + 2e- reversible arrow Rh(I)) and the pK(a) values ([Rh(III)H](+) reversible arrow Rh(I) + H+) are also different. From the observed trends it is concluded that the catalytic activity of the rhodium complexes depends on its position in the bilayer.

  DOI：

  10.1021/jo00111a018
• 作为产物：
  描述：

  5-甲基-2,2'-联吡啶 在 4-二甲氨基吡啶 、 potassium permanganate 、 氯化亚砜 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 36.0h， 生成 2,2'-Bipyridine-5-N-(6-hydroxyhexyl)carboxamide
  参考文献：
  名称：

  Reduction of Nicotinamides, Flavins, and Manganese Porphyrins by Formate, Catalyzed by Membrane-Bound Rhodium Complexes

  摘要：

  Two polymerizable cyclopentadienyl-2,2'-bipyridinerhodium complexes and one amphiphilic rhodium complex have been synthesized and incorporated into the bilayers of vesicles formed from a polymerizable ammonium surfactant. Incorporation was achieved by chemical linkage (via a copolymerization reaction) or by physical absorption. The complexes are located at different positions in the bilayer, viz, in the hydrophobic interior or at the aqueous interface. The anchored rhodium complexes efficiently catalyze the reduction of both two-electron substrates (e.g., nicotinamides and flavin) and one-electron substrates (e.g., manganese(III) porphyrins) by sodium formate. Kinetic studies indicate that the rate-limiting step of the reaction is the reduction of the rhodium center by formate, leading to a rhodium(III) hydride or a rhodium(I) species. The three complexes showed different catalytic activities. Cyclic voltammetry and UV-vis measurements revealed that their reduction potentials ([Rh(III)](2+) + 2e- reversible arrow Rh(I)) and the pK(a) values ([Rh(III)H](+) reversible arrow Rh(I) + H+) are also different. From the observed trends it is concluded that the catalytic activity of the rhodium complexes depends on its position in the bilayer.

  DOI：

  10.1021/jo00111a018

文献信息

• Reduction of Nicotinamides, Flavins, and Manganese Porphyrins by Formate, Catalyzed by Membrane-Bound Rhodium Complexes
  作者：J. H. van Esch、M. A. M. Hoffmann、R. J. M. Nolte

  DOI：10.1021/jo00111a018

  日期：1995.3

  Two polymerizable cyclopentadienyl-2,2'-bipyridinerhodium complexes and one amphiphilic rhodium complex have been synthesized and incorporated into the bilayers of vesicles formed from a polymerizable ammonium surfactant. Incorporation was achieved by chemical linkage (via a copolymerization reaction) or by physical absorption. The complexes are located at different positions in the bilayer, viz, in the hydrophobic interior or at the aqueous interface. The anchored rhodium complexes efficiently catalyze the reduction of both two-electron substrates (e.g., nicotinamides and flavin) and one-electron substrates (e.g., manganese(III) porphyrins) by sodium formate. Kinetic studies indicate that the rate-limiting step of the reaction is the reduction of the rhodium center by formate, leading to a rhodium(III) hydride or a rhodium(I) species. The three complexes showed different catalytic activities. Cyclic voltammetry and UV-vis measurements revealed that their reduction potentials ([Rh(III)](2+) + 2e- reversible arrow Rh(I)) and the pK(a) values ([Rh(III)H](+) reversible arrow Rh(I) + H+) are also different. From the observed trends it is concluded that the catalytic activity of the rhodium complexes depends on its position in the bilayer.