N,N'-[1,4-butanediylbis(oxy-7,1-naphthalenediyl)]bis(2-pyridinecarboxamide) | 1367358-46-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: N,N'-[1,4-butanediylbis(oxy-7,1-naphthalenediyl)]bis(2-pyridinecarboxamide)
• 英文别名: N-[7-[4-[8-(pyridine-2-carbonylamino)naphthalen-2-yl]oxybutoxy]naphthalen-1-yl]pyridine-2-carboxamide
• CAS: 1367358-46-0
• 化学式: C₃₆H₃₀N₄O₄
• 分子量: 582.659
• InChiKey: PWGVYVFUKPRMCF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7
• 重原子数：
  44
• 可旋转键数：
  11
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  102
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  dichloro(cycloocta-1,5-diene)palladium (II) 、 N,N'-[1,4-butanediylbis(oxy-7,1-naphthalenediyl)]bis(2-pyridinecarboxamide) 在 Et₃N 作用下， 以 氯仿 为溶剂， 以20%的产率得到[[N,N'-[1,4-butanediylbis(oxy-7,1-naphthalenediyl)]bis(2-pyridinecarboxamidato)]-κN(1),κN(1)',κN(2),κN(2)']palladium
  参考文献：
  名称：

  Planar-Chiral Metal Complexes Comprised of Square-Planar Metal and Achiral Tetradentate Ligands: Design, Optical Resolution, and Thermodynamics

  摘要：

  Planar-chiral palladium complexes {[{N,N'-[1,4-butanediylbis(oxy-7,1-naphthalenediyl)]bis(2- pyridinecarboxamidato)](2-)-kappa N-1',kappa N-1',kappa N-2,kappa N-2']palladium (PdL4) and [[2,2'-[1,4-butanediylbis[[(oxy-7,1-naphthalenediyl)]mino]methyl]]dipyrrolato](2)kappa N-1,kappa N-1',kappa N-2,kappa N-2']palladium (PdL5)} were synthesized from achiral tetradentate ligands N,N'[1,4-butanediylbis(oxy-7,1-naphthalenediyl)]bis(2-pyridinecarboxamide) (H2L4) and N,N'bis[(H-1-pyrrol-2-yl]methylidene]-7,7'-(1,4-butanediyldioxy)bis- (1-naphthalenamine) (H2L5) bearing two dissymmetric bidentate units at both ends and a Pd-II ion, respectively. The palladium complexes were crystallized in the monoclinic space group P2(1)/n with the unit cell parameters a = 16.5464(6) angstrom, b = 11.3534(4) angstrom, c = 17.6697(7) angstrom, beta = 115.5300(10)degrees, and Z = 4 for PdL4 and a = 17.2271(8) angstrom, b = 10.1016(5) angstrom, c = 17.9361(9) angstrom, beta = 105.6310(10)degrees, and Z = 4 for PaL5.. The planar-chiral structures of PdL4 and PdL5 were confirmed by single-crystal X-ray analyses, resulting in the fact that the crystals were racemic mixtures. The racemic mixtures were successfully resolved by using chiral high-performance liquid-chromatography techniques. Racemizations of the complexes were found to be drastically dependent on the arrangement of the charged or uncharged metal-binding N atoms of the ligands.

  DOI：

  10.1021/ic2024742
• 作为产物：
  描述：

  2-吡啶甲酰氯 、 7,7'-(1,4-butanediyldioxy)bis(1-naphthalenamine) 在 吡啶 作用下， 以 苯 为溶剂， 反应 3.0h， 以0.64 g的产率得到N,N'-[1,4-butanediylbis(oxy-7,1-naphthalenediyl)]bis(2-pyridinecarboxamide)
  参考文献：
  名称：

  Planar-Chiral Metal Complexes Comprised of Square-Planar Metal and Achiral Tetradentate Ligands: Design, Optical Resolution, and Thermodynamics

  摘要：

  Planar-chiral palladium complexes {[{N,N'-[1,4-butanediylbis(oxy-7,1-naphthalenediyl)]bis(2- pyridinecarboxamidato)](2-)-kappa N-1',kappa N-1',kappa N-2,kappa N-2']palladium (PdL4) and [[2,2'-[1,4-butanediylbis[[(oxy-7,1-naphthalenediyl)]mino]methyl]]dipyrrolato](2)kappa N-1,kappa N-1',kappa N-2,kappa N-2']palladium (PdL5)} were synthesized from achiral tetradentate ligands N,N'[1,4-butanediylbis(oxy-7,1-naphthalenediyl)]bis(2-pyridinecarboxamide) (H2L4) and N,N'bis[(H-1-pyrrol-2-yl]methylidene]-7,7'-(1,4-butanediyldioxy)bis- (1-naphthalenamine) (H2L5) bearing two dissymmetric bidentate units at both ends and a Pd-II ion, respectively. The palladium complexes were crystallized in the monoclinic space group P2(1)/n with the unit cell parameters a = 16.5464(6) angstrom, b = 11.3534(4) angstrom, c = 17.6697(7) angstrom, beta = 115.5300(10)degrees, and Z = 4 for PdL4 and a = 17.2271(8) angstrom, b = 10.1016(5) angstrom, c = 17.9361(9) angstrom, beta = 105.6310(10)degrees, and Z = 4 for PaL5.. The planar-chiral structures of PdL4 and PdL5 were confirmed by single-crystal X-ray analyses, resulting in the fact that the crystals were racemic mixtures. The racemic mixtures were successfully resolved by using chiral high-performance liquid-chromatography techniques. Racemizations of the complexes were found to be drastically dependent on the arrangement of the charged or uncharged metal-binding N atoms of the ligands.

  DOI：

  10.1021/ic2024742

文献信息

• Planar-Chiral Metal Complexes Comprised of Square-Planar Metal and Achiral Tetradentate Ligands: Design, Optical Resolution, and Thermodynamics
  作者：Hidetoshi Goto、Teppei Hayakawa、Kanako Furutachi、Hiroshi Sugimoto、Shohei Inoue

  DOI：10.1021/ic2024742

  日期：2012.4.2

  Planar-chiral palladium complexes [N,N'-[1,4-butanediylbis(oxy-7,1-naphthalenediyl)]bis(2- pyridinecarboxamidato)](2-)-kappa N-1',kappa N-1',kappa N-2,kappa N-2']palladium (PdL4) and [[2,2'-[1,4-butanediylbis[[(oxy-7,1-naphthalenediyl)]mino]methyl]]dipyrrolato](2)kappa N-1,kappa N-1',kappa N-2,kappa N-2']palladium (PdL5)} were synthesized from achiral tetradentate ligands N,N'[1,4-butanediylbis(oxy-7,1-naphthalenediyl)]bis(2-pyridinecarboxamide) (H2L4) and N,N'bis[(H-1-pyrrol-2-yl]methylidene]-7,7'-(1,4-butanediyldioxy)bis- (1-naphthalenamine) (H2L5) bearing two dissymmetric bidentate units at both ends and a Pd-II ion, respectively. The palladium complexes were crystallized in the monoclinic space group P2(1)/n with the unit cell parameters a = 16.5464(6) angstrom, b = 11.3534(4) angstrom, c = 17.6697(7) angstrom, beta = 115.5300(10)degrees, and Z = 4 for PdL4 and a = 17.2271(8) angstrom, b = 10.1016(5) angstrom, c = 17.9361(9) angstrom, beta = 105.6310(10)degrees, and Z = 4 for PaL5.. The planar-chiral structures of PdL4 and PdL5 were confirmed by single-crystal X-ray analyses, resulting in the fact that the crystals were racemic mixtures. The racemic mixtures were successfully resolved by using chiral high-performance liquid-chromatography techniques. Racemizations of the complexes were found to be drastically dependent on the arrangement of the charged or uncharged metal-binding N atoms of the ligands.