N,N'-bis(2-hydroxy-5-methoxybenzylidene)-propane-1,2-diamine | 324059-19-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: N,N'-bis(2-hydroxy-5-methoxybenzylidene)-propane-1,2-diamine
• 英文别名: N,N'-bis(2-hydroxy-5-methoxybenzylidene)propane-1,2-diamine；N,N-bis(2-hydroxy-5-methoxybenzylidene)propane-1,2-diamine；bis-(5-methoxysalicylidene)-1,2-diaminopropane；H2(2h5mb)2pn；2-{(E)-[(2-{[(1E)-(2-hydroxy-5-methoxyphenyl)methylene]amino}-1-methylethyl)imino]methyl}-4-methoxyphenol；2-[2-[(2-hydroxy-5-methoxyphenyl)methylideneamino]propyliminomethyl]-4-methoxyphenol
• CAS: 324059-19-0
• 化学式: C₁₉H₂₂N₂O₄
• 分子量: 342.395
• InChiKey: XXLFQUBZGNWHHK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  25
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  83.6
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  N,N'-bis(2-hydroxy-5-methoxybenzylidene)-propane-1,2-diamine 生成 N,N-bis(2-hydroxy-5-methoxybenzylidene)propane-1,2-diamine
  参考文献：
  名称：

  Synthesis, spectral, photolysis and electrochemical studies of mononuclear copper(II) complex with a new asymmetric tetradentate ligand: Application as copper nanoparticle precursor

  摘要：

  A copper(II) complex with asymmetric tetradentate Schiff base ligand, obtained by the single condensation of 1,2-diaminopropane with 2-hydroxy-5-methoxy benzaldehyde was prepared. The ligand and complex were characterized by their IR, UV-Vis, FT-IR, NMR spectra and CV. Crystal structures of the mononuclear copper complex have been obtained by X-ray diffraction studies which revealed to be distorted square planner coordination geometry. The spectral data confirm coordination of ligand to copper ion center. The redox properties of complex at different scan rates exhibit grossly similar features consisting of an electrochemically pseudo-reversible Cu(II)/Cu(I) reduction at ca. -0.97 V and pseudo-reversible Cu(I)/Cu(II) oxidation at ca. -0.81 V. The copper nanoparticles with average size of 73 nm were formed by thermal reduction of copper complex in the presence of triphenylphosphine. (C)0 2012 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.saa.2012.05.081
• 作为产物：
  描述：

  2-羟基-5-甲氧基苯甲醛 、 1,2-丙二胺 以 甲醇 为溶剂， 以73%的产率得到N,N'-bis(2-hydroxy-5-methoxybenzylidene)-propane-1,2-diamine
  参考文献：
  名称：

  两种新的含1,2-丙二胺和2-羟基-5-甲氧基苯甲醛配体的锰配合物的合成，晶体结构和电化学性质

  摘要：

  两种新的均双核锰（III）配合物[Mn（L）（H 2 O）] 2（PF 6）2，其中[H 2 L = N，N'-双（2-羟基-5-甲氧基-亚苄基） ）-丙烷-1,2-二胺]是通过将N，N'-双（2-羟基-5-甲氧基亚苄基）丙烷-1,2-二胺作为席夫碱配体与乙酸锰（II）反应制得的和六氟磷酸铵。通过光谱，结构和电化学研究表征了该配合物。X射线结构分析表明配合物中存在二锰核，配位体通过N 2 O 2与锰（III）结合。。二聚体单元由一个具有中心对称同系物的分子的双Mn-O桥形成。配合物的晶体结构表明，在固态下，配合物采用亚胺N和羟基O的八面体环境，其中一个轴向H 2 O配体围绕锰。每个双核复合物的两个锰中心周围存在两个协调/螯合环境。络合物的电子光谱在d–d跃迁中显示出红移。这些络合物在乙腈溶液中的玻璃碳电极上的电化学还原表明，对应于Mn（III）-Mn（II）的第一个还原过程在0至-1.0 V的范围内是电化学可逆的。

  DOI：

  10.1080/15533174.2012.740740

文献信息

• Taqui Khan, M. M.; Shaikh, Z. A.; Kureshy, R. I., Polyhedron, 1992, vol. 11, p. 91 - 100
  作者：Taqui Khan, M. M.、Shaikh, Z. A.、Kureshy, R. I.、Boricha, A. B.

  DOI：——

  日期：——
• Facile, Efficient, and Diastereoselective Synthesis of Heterohelicene-like Molecules
  作者：Wei Lin、Guo-Lan Dou、Ming-Hua Hu、Cheng-Pao Cao、Zhi-Bin Huang、Da-Qing Shi

  DOI：10.1021/ol400154j

  日期：2013.3.15

  A concise and efficient route to new and interesting heterohelicene-like molecules has been developed through the one-pot, cascade reductive coupling reaction of o-hydroxydiimines or o-nitrodiimines and triphosgene in the presence of TiCl4/Sm. Purification of the final products only required a single recrystallization leading to high purity. High diastereoselectivity was also achieved, and two structures of the final products were confirmed by X-ray diffraction analysis.
• Salicylidene-imine-zirconium(IV) complexes in combination with methylalumoxane as catalysts for the conversion of hexa-1,5-diene: adjusting of the catalytic activity
  作者：Bernd Schweder、Dirk Walther、Thomas Döhler、Olaf Klobes、Helmar Görls

  DOI：10.1002/(sici)1521-3897(199911)341:8<736::aid-prac736>3.0.co;2-v

  日期：1999.11

  A variety of substituted Schiff base complexes of the composition ("salen")ZrCl2(thf)(1-21) were synthesized, with methylalumoxane ("MAO") activated and used for a systematic study of their catalytic activity towards hexa-1,5-diene ("salen": substituted salicylidene-ethylene-iminato ligands). Main product of the catalytic cycle is methylenecyclopentane. Dimers are only formed in minor amounts. The catalytic activity and selectivity of the Ziegler-Natta systems strongly depend on the nature and the position of the peripheric substituents in the Schiff base ligands. Electron-withdrawing substituents in para-position to the phenolate oxygen (5-position) decrease the catalytic activity. Improved activity and selectivity were obtained with electron-donating substituents in 5-position. Altering the ethylene bridge causes a lowering of the activity or inactivation. According to the X-ray analysis the metal center in the related complex (L)ZrCl2 (22) (L: N',N'-bis(ethylene)-N'-methyl-N,N"-bis(benzoylacetonatoimine) has a pentagonal-bipyramidal environment. The pentadentate Schiff base Ligand lies in the plane, and both chloro groups occupy the axial positions. In contrast to the catalytically active salene complexes 22 can not rearrange to form a species in which the both chlorides are cis to each other. Consequently 22 is catalytically inactive.
• Syntheses, spectral, electrochemical and thermal studies of mononuclear manganese(III) complexes with ligands derived from 1,2-propanediamine and 2-hydroxy-3 or 5-methoxybenzaldehyde: Self-assembled monolayer formation on nanostructure zinc oxide thin film
  作者：Mohammad Hossein Habibi、Elham Askari、Mehdi Amirnasr、Ahmad Amiri、Yuki Yamane、Takayoshi Suzuki

  DOI：10.1016/j.saa.2011.03.055

  日期：2011.8

  Mononuclear Mn(III) complexes have been prepared via the Mn(II) reaction of an equimolar of Schiff-bases derived from reaction of 2-hydroxy-3-methoxybenzaldehyde or 2-hydroxy-5-methoxybenzaldehyde with 1,2-diaminopropane. Axial ligands L include: pyridine (py) and H2O. The resulting complexes have been characterized by FT-IR and UV-vis spectroscopy. The crystal structures of the complexes were determined and indicate that in the solid state the complex adopts a slightly distorted octahedral environment of the imine N and hydroxo O with the two axial ligands. The electrochemical reduction of these complexes at a glassy carbon electrode in acetonitrile solution indicates that the first reduction process corresponding to Mn-III-Mn-II is electrochemically quasi-reversible. Thermal stability of these complexes was determined by TG and DTG. Layers of these complexes were formed on nanostructure zinc oxide thin film and a red shift was observed when zinc oxide thin film is modified by complex. (C) 2011 Elsevier B.V. All rights reserved.