benzo[1,2'h:5,4-h']di(4-methylquinoline) | 1351191-71-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: benzo[1,2'h:5,4-h']di(4-methylquinoline)
• 英文别名: 8,18-Dimethyl-5,21-diazapentacyclo[12.8.0.03,12.04,9.017,22]docosa-1(14),2,4,6,8,10,12,15,17,19,21-undecaene；8,18-dimethyl-5,21-diazapentacyclo[12.8.0.03,12.04,9.017,22]docosa-1(14),2,4,6,8,10,12,15,17,19,21-undecaene
• CAS: 1351191-71-3
• 化学式: C₂₂H₁₆N₂
• 分子量: 308.382
• InChiKey: FZJIMOLTHOFRIO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  24
• 可旋转键数：
  0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  25.8
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  benzo[1,2'h:5,4-h']di(4-methylquinoline) 、 lithium chloride 、 palladium dichloride 以 甲醇 为溶剂， 以87%的产率得到
  参考文献：
  名称：

  Synthesis, characterization, and cyclometalation studies of benzo[1,2-h: 5,4-h′]diquinolines with palladium and platinum

  摘要：

  Benzo[1,2-h: 5,4-h']diquinoline(1a) represents a new family of tridentate NCN pincer ligand. We report the synthesis of the parent ligand (1a) and its derivatives (1b R = Me, 1c R = t-Butyl, 1d R = Phenyl). The ligands were characterized by H-1 and C-13 NMR, as well as mass spectral analysis, and X-ray structural determination. They readily undergo cyclometalation with LiPdCl4, Pd(OAc)(2), and K2PtCl4 to form the cyclometalated Pd(NCN) Cl (2a-c, 3a), and Pt(NCN)Cl (4a) pincer complexes. These complexes have been characterized through NMR, and mass spectrometry. PdNCNCl (2a) structure was determined by single crystal X-ray diffraction. Complex 2a has shown to catalyze the Heck coupling reaction between bromobenzene and n-butylacyrlate in NMP at 140 degrees C, TON of 2506 were observed. (C) 2011 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jorganchem.2011.08.012
• 作为产物：
  描述：

  1,8-二氨基蒽醌 在 sodium tetrahydroborate 、 溶剂黄146 作用下， 以 丙醛 、 硝基苯 为溶剂， 反应 72.0h， 生成 、 、 benzo[1,2'h:5,4-h']di(4-methylquinoline)
  参考文献：
  名称：

  Synthesis, characterization, and cyclometalation studies of benzo[1,2-h: 5,4-h′]diquinolines with palladium and platinum

  摘要：

  Benzo[1,2-h: 5,4-h']diquinoline(1a) represents a new family of tridentate NCN pincer ligand. We report the synthesis of the parent ligand (1a) and its derivatives (1b R = Me, 1c R = t-Butyl, 1d R = Phenyl). The ligands were characterized by H-1 and C-13 NMR, as well as mass spectral analysis, and X-ray structural determination. They readily undergo cyclometalation with LiPdCl4, Pd(OAc)(2), and K2PtCl4 to form the cyclometalated Pd(NCN) Cl (2a-c, 3a), and Pt(NCN)Cl (4a) pincer complexes. These complexes have been characterized through NMR, and mass spectrometry. PdNCNCl (2a) structure was determined by single crystal X-ray diffraction. Complex 2a has shown to catalyze the Heck coupling reaction between bromobenzene and n-butylacyrlate in NMP at 140 degrees C, TON of 2506 were observed. (C) 2011 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jorganchem.2011.08.012

文献信息

• Synthesis, characterization, and cyclometalation studies of benzo[1,2-h: 5,4-h′]diquinolines with palladium and platinum
  作者：Kenneth J.H. Young、Xianhui Bu、William C. Kaska

  DOI：10.1016/j.jorganchem.2011.08.012

  日期：2011.12

  Benzo[1,2-h: 5,4-h']diquinoline(1a) represents a new family of tridentate NCN pincer ligand. We report the synthesis of the parent ligand (1a) and its derivatives (1b R = Me, 1c R = t-Butyl, 1d R = Phenyl). The ligands were characterized by H-1 and C-13 NMR, as well as mass spectral analysis, and X-ray structural determination. They readily undergo cyclometalation with LiPdCl4, Pd(OAc)(2), and K2PtCl4 to form the cyclometalated Pd(NCN) Cl (2a-c, 3a), and Pt(NCN)Cl (4a) pincer complexes. These complexes have been characterized through NMR, and mass spectrometry. PdNCNCl (2a) structure was determined by single crystal X-ray diffraction. Complex 2a has shown to catalyze the Heck coupling reaction between bromobenzene and n-butylacyrlate in NMP at 140 degrees C, TON of 2506 were observed. (C) 2011 Elsevier B.V. All rights reserved.