N-[(4-methoxynaphthalen-1-yl)methylideneamino]benzamide | 316131-96-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: N-[(4-methoxynaphthalen-1-yl)methylideneamino]benzamide
• CAS: 316131-96-1
• 化学式: C₁₉H₁₆N₂O₂
• 分子量: 304.348
• InChiKey: ZXLLWZJXDAKLKW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  50.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-[(4-methoxynaphthalen-1-yl)methylideneamino]benzamide 以 甲醇 、 丙酮 为溶剂， 反应 73.0h， 生成
  参考文献：
  名称：

  Regioselective cyclometallation of 4-R-1-naphthaldehyde benzoylhydrazones: Palladium(II) complexes with CNO pincer like ligands

  摘要：

  Reactions of Li2PdCl4, 4-R-1-naphthaldehyde benzoylhydrazones (H2Ln; n = 1 and 2 for R = H and OMe, respectively) and NaOAc center dot 3H(2)O in 1:1:1 mole ratio in methanol provide the cyclopalladated complexes with the general formula [Pd(HLn)Cl] (1 (R = H) and 2 (R = OMe)). Treatment of one mole equivalent of [Pd(HLn)Cl] (1 and 2) with two mole equivalents of PPh3 in acetone results in the deprotonation of the O-coordinated amide functionality and the replacement of the metal coordinated chloride with PPh3 leading to the formation of [Pd(L-n)(PPh3)] (3 and 4). All the complexes have been characterized with the help of elemental analysis and spectroscopic (IR, UV-vis and H-1 NMR) measurements. NMR spectra indicates the peri-metallation of the 1-naphthalenyl fragment of the tridentate ligand in 1-4. Molecular structures determined by X-ray crystallography confirm the regioselective peri-metallation in each of 2, 3 and 4. (C) 2013 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jorganchem.2013.02.007
• 作为产物：
  描述：

  4-甲氧基-1-萘甲醛 、 苯甲酰肼 在 溶剂黄146 作用下， 以 乙醇 为溶剂， 反应 3.0h， 以85%的产率得到N-[(4-methoxynaphthalen-1-yl)methylideneamino]benzamide
  参考文献：
  名称：

  Regioselective cyclometallation of 4-R-1-naphthaldehyde benzoylhydrazones: Palladium(II) complexes with CNO pincer like ligands

  摘要：

  Reactions of Li2PdCl4, 4-R-1-naphthaldehyde benzoylhydrazones (H2Ln; n = 1 and 2 for R = H and OMe, respectively) and NaOAc center dot 3H(2)O in 1:1:1 mole ratio in methanol provide the cyclopalladated complexes with the general formula [Pd(HLn)Cl] (1 (R = H) and 2 (R = OMe)). Treatment of one mole equivalent of [Pd(HLn)Cl] (1 and 2) with two mole equivalents of PPh3 in acetone results in the deprotonation of the O-coordinated amide functionality and the replacement of the metal coordinated chloride with PPh3 leading to the formation of [Pd(L-n)(PPh3)] (3 and 4). All the complexes have been characterized with the help of elemental analysis and spectroscopic (IR, UV-vis and H-1 NMR) measurements. NMR spectra indicates the peri-metallation of the 1-naphthalenyl fragment of the tridentate ligand in 1-4. Molecular structures determined by X-ray crystallography confirm the regioselective peri-metallation in each of 2, 3 and 4. (C) 2013 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jorganchem.2013.02.007

文献信息

• Regioselective cyclometallation of 4-R-1-naphthaldehyde benzoylhydrazones: Palladium(II) complexes with CNO pincer like ligands
  作者：A.R. Balavardhana Rao、Samudranil Pal

  DOI：10.1016/j.jorganchem.2013.02.007

  日期：2013.5

  Reactions of Li2PdCl4, 4-R-1-naphthaldehyde benzoylhydrazones (H2Ln; n = 1 and 2 for R = H and OMe, respectively) and NaOAc center dot 3H(2)O in 1:1:1 mole ratio in methanol provide the cyclopalladated complexes with the general formula [Pd(HLn)Cl] (1 (R = H) and 2 (R = OMe)). Treatment of one mole equivalent of [Pd(HLn)Cl] (1 and 2) with two mole equivalents of PPh3 in acetone results in the deprotonation of the O-coordinated amide functionality and the replacement of the metal coordinated chloride with PPh3 leading to the formation of [Pd(L-n)(PPh3)] (3 and 4). All the complexes have been characterized with the help of elemental analysis and spectroscopic (IR, UV-vis and H-1 NMR) measurements. NMR spectra indicates the peri-metallation of the 1-naphthalenyl fragment of the tridentate ligand in 1-4. Molecular structures determined by X-ray crystallography confirm the regioselective peri-metallation in each of 2, 3 and 4. (C) 2013 Elsevier B.V. All rights reserved.