2-羟基-5-甲基-3-[(4-甲基哌嗪-1-基)甲基]苯甲醛 | 155454-68-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 2-羟基-5-甲基-3-[(4-甲基哌嗪-1-基)甲基]苯甲醛
• 英文名称: 2-Formyl-4-methyl-6-<(4-methylpiperazin-1-yl)methyl>phenol
• 英文别名: 2-formyl-4-methyl-6-[(4-methylpiperazine-1-yl)methyl] phenol；2-formyl-4-methyl-6-[(4-methylpiperazine-1-yl)methyl]phenol；2-formyl-4-methyl-6-((4-methylpiperazin-1-yl)methyl)phenol；Benzaldehyde, 2-hydroxy-5-methyl-3-[(4-methyl-1-piperazinyl)methyl]-；2-hydroxy-5-methyl-3-[(4-methylpiperazin-1-yl)methyl]benzaldehyde
• CAS: 155454-68-5
• 化学式: C₁₄H₂₀N₂O₂
• 分子量: 248.325
• InChiKey: LMQKBGRALSTILZ-UHFFFAOYSA-N

物化性质

• 熔点：
  83-84 °C(Solv: hexane (110-54-3))
• 沸点：
  355.3±42.0 °C(Predicted)
• 密度：
  1.164±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  43.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-羟基-5-甲基-3-[(4-甲基哌嗪-1-基)甲基]苯甲醛 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 为溶剂， 反应 16.0h， 生成 4-Methyl-2-<(4-methylpiperazin-1-yl)methyl>-6-<methyl>phenol
  参考文献：
  名称：

  A New Method for the Synthesis of Nonsymmetric Dinucleating Ligands by Aminomethylation of Phenols and Salicylaldehydes

  摘要：

  Monoaminomethylated phenols 5-7 and symmetrically diaminomethylated phenols 8 and 9 were prepared in a one-step procedure-from p-cresol, formaldehyde, and a variety of secondary amines by making use of the aromatic Mannich reaction. Nonsymmetric diaminomethylated phenols 10 and 11 were prepared by a sequential aromatic Mannich reaction using p-cresol, formaldehyde, and two different secondary amines. Alternatively, nonsymmetric diaminomethylated phenols 20-24 were prepared by aminomethylation of 5-methylsalicylaldehyde followed by Ca) condensation with a primary amine and subsequent reduction or (b) reductive amination with a secondary amine. Monoami-nomethylated and (non)symmetric diaminomethylated phenols are excellent ligands for the synthesis of mono- and dinuclear transition metal complexes as is illustrated by the isolation of mononuclear iron(III) complex 25 and nonsymmetric dinuclear copper(II) complex 26.

  DOI：

  10.1021/jo00087a046
• 作为产物：
  描述：

  N-甲基哌嗪 、 聚合甲醛 、 5-甲基水杨醛 生成 2-羟基-5-甲基-3-[(4-甲基哌嗪-1-基)甲基]苯甲醛
  参考文献：
  名称：

  A New Method for the Synthesis of Nonsymmetric Dinucleating Ligands by Aminomethylation of Phenols and Salicylaldehydes

  摘要：

  Monoaminomethylated phenols 5-7 and symmetrically diaminomethylated phenols 8 and 9 were prepared in a one-step procedure-from p-cresol, formaldehyde, and a variety of secondary amines by making use of the aromatic Mannich reaction. Nonsymmetric diaminomethylated phenols 10 and 11 were prepared by a sequential aromatic Mannich reaction using p-cresol, formaldehyde, and two different secondary amines. Alternatively, nonsymmetric diaminomethylated phenols 20-24 were prepared by aminomethylation of 5-methylsalicylaldehyde followed by Ca) condensation with a primary amine and subsequent reduction or (b) reductive amination with a secondary amine. Monoami-nomethylated and (non)symmetric diaminomethylated phenols are excellent ligands for the synthesis of mono- and dinuclear transition metal complexes as is illustrated by the isolation of mononuclear iron(III) complex 25 and nonsymmetric dinuclear copper(II) complex 26.

  DOI：

  10.1021/jo00087a046

文献信息

• Amino-salicylaldimine–palladium(II) complexes: New and efficient catalysts for Suzuki and Heck reactions
  作者：Jin Cui、Mingjie Zhang、Yuwei Zhang

  DOI：10.1016/j.inoche.2009.10.023

  日期：2010.1

  alladium(II) complexes bearing 5-methyl-3-(R-1-ylmethyl)-salicylaldimine ligands (R = morpholine, piperidine, pyrrolidine, 4-methylpiperazin, diisopropylamine) have been prepared and characterized by IR, 1H NMR and elemental analysis. Crystal structure details of complex 2b have been confirmed by X-ray structure analysis. The obtained Pd(II) complexes were found to be effective catalysts for the Suzuki

  摘要 制备并表征了一系列带有 5-甲基-3-(R-1-基甲基)-水杨醛亚胺配体（R = 吗啉、哌啶、吡咯烷、4-甲基哌嗪、二异丙胺）的氨基-水杨醛亚胺-钯 (II) 配合物通过 IR、1H NMR 和元素分析。配合物 2b 的晶体结构细节已通过 X 射线结构分析得到证实。发现获得的 Pd(II) 配合物是 Suzuki 和 Heck 交叉偶联反应的有效催化剂，该反应可以在空气中的未干燥溶剂中进行。
• Synthesis of unsymmetrical ‘end-off’ phenoxo and oximinato di bridged copper(II) and nickel(II) complexes: spectral, electrochemical and magnetic properties
  作者：D. Saravanakumar、N. Sengottuvelan、G. Priyadarshni、M. Kandaswamy、H. Okawa

  DOI：10.1016/j.poly.2003.11.004

  日期：2004.2

  interaction (μeff: 1.55–1.58 BM) at 298 K with a broad EPR signal (g=2.1). Variable temperature magnetic susceptibility study of the binuclear copper(II) complex [Cu2L1](ClO4)2 · 2H2O (5) shows the observed −2J value is 283 cm−1. The mononuclear copper(II) complexes have a magnetic moment value close to the spin only value with four hyperfine EPR signals.

  通式[ML 1 ]（ClO 4）·H 2 O，[M 2 L 1 ]（ClO 4）2  ·2H 2 O，[ML ]的新型单核和不对称双核铜（II）和镍（II）配合物2-（ClO 4）·H 2 O和[M 2 L 2 ]（ClO 4）2  ·2H 2 O通过2-甲酰基-4-甲基-6-[（4-甲基哌嗪-1基）的缩合反应制得）甲基]苯酚（1）与N -β-氨基乙基异亚硝基乙基甲基酮亚胺（PCI）或NM（II）盐（其中M = Cu和Ni）存在下的-β-氨基甲基乙基异亚硝基乙基甲基酮亚胺（PCII）。通过元素分析和光谱分析对复合物进行表征。循环伏安法研究证明，在阴极区域中所有单核络合物都存在一个准可逆的还原波。对于阴极区域中的所有双核络合物，获得了两个拟可逆的一个电子还原波。双核铜（II）配合物示出了反铁磁交互（μ EFF：1.55-1.58 BM）在298K具有宽的EPR信号（克= 2.1）。双核铜（II）配合物[Cu
• Synthesis, characterization and electrochemical behavior of new acyclic mono and binuclear copper (II) complexes: DNA binding and cleavage studies
  作者：Elumalai Sundaravadivel、Kandaswamy Muthusamy、Babu Varghese

  DOI：10.1016/j.poly.2013.04.057

  日期：2013.9

  A new series of acyclic mono and binuclear copper (II) complexes of the general formula [Cu(L1-5)](ClO4)(H2O)(2) (1-5) and [Cu-2(L1-5)(H2O)(2)](ClO4)(2) (6-10), L1-5 refers to [N-(salicylaldimine)N'-[(2-formyl-4-methyl-6-(4-methylpiperazine-1-yl)methyl)phenol] diamines, where the diamines are L-1 = 1,2-diamino ethane, L-2 = 1,3-diamino propane, 1.3 = 1,2-diamino benzene, L-4 = 2-aminobenzylamine and L-5 = 1,8-diamino naphthalene) have been synthesized and characterized. From the single crystal X-ray diffraction method, the mononuclear complex [Cu(L-1)](ClO4)(H2O)(2) (1), in which the copper atom exhibits a distorted square planar geometry, coordinates with two phenolic oxygen atoms and two ethylenediamine nitrogen atoms. The coordination bond angles have values between 83.7(2)degrees [N1-Cu1-N2] and 94.08(19)degrees [O2-Cu1-N2]. Electrochemical studies were performed using cyclic voltammetry, in which the appearance of one quasi-reversible peak within the potential range -0.91 to -1.21 V (E-pc) for mononuclear and two quasi-reversible peaks within the potential ranges -0.70 to -0.88 V (E-pc(1)) and -0.96 to -1.15 V (E-pc(2)) for binuclear complexes were observed respectively. The CT-DNA binding ability of the complexes was investigated using absorption and fluorescence spectroscopic studies, viscosity measurements and circular dichroic techniques. In the absorption spectra, the binding constant (K-b) values for all the complexes were found to be of the order of 0.4 x 10(4)-5.5 x 10(4) and from fluorescence spectra the apparent binding constant (K-app) values were of the order of 1.7 x 10(6)-6.6 x 10(6). From the above K-b and K-app values, the binding propensity of the complexes to CT-DNA is revealed to be through the intercalative mode. The complexes cleave supercoiled pBR322 DNA in the presence of mercaptoethanol as a reducing agent and with a mechanistic pathway involving the formation of singlet oxygen as a reactive oxygen species. Overall, the more aromatic containing binuclear Cu(II) complex (10) exhibits better DNA binding and cleavage activity than the substituted aliphatic complexes. (C) 2013 Elsevier Ltd. All rights reserved.
• Lubben, Marcel; Hage, Ronald; Meetsma, Auke, Inorganic Chemistry, 1995, vol. 34, # 8, p. 2217 - 2224
  作者：Lubben, Marcel、Hage, Ronald、Meetsma, Auke、Bÿma, Koos、Feringa, Ben L.

  DOI：——

  日期：——
• A New Method for the Synthesis of Nonsymmetric Dinucleating Ligands by Aminomethylation of Phenols and Salicylaldehydes
  作者：Marcel Lubben、Ben L. Feringa

  DOI：10.1021/jo00087a046

  日期：1994.4

  Monoaminomethylated phenols 5-7 and symmetrically diaminomethylated phenols 8 and 9 were prepared in a one-step procedure-from p-cresol, formaldehyde, and a variety of secondary amines by making use of the aromatic Mannich reaction. Nonsymmetric diaminomethylated phenols 10 and 11 were prepared by a sequential aromatic Mannich reaction using p-cresol, formaldehyde, and two different secondary amines. Alternatively, nonsymmetric diaminomethylated phenols 20-24 were prepared by aminomethylation of 5-methylsalicylaldehyde followed by Ca) condensation with a primary amine and subsequent reduction or (b) reductive amination with a secondary amine. Monoami-nomethylated and (non)symmetric diaminomethylated phenols are excellent ligands for the synthesis of mono- and dinuclear transition metal complexes as is illustrated by the isolation of mononuclear iron(III) complex 25 and nonsymmetric dinuclear copper(II) complex 26.