2,2'-[propane-1,3-diylbis(iminomethylene)]bis(6-methoxyphenol) | 5767-55-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 2,2'-[propane-1,3-diylbis(iminomethylene)]bis(6-methoxyphenol)
• 英文别名: (1,3-propanediyl)bis(iminomethylene)bis(6-methoxyphenol)；bis(2-hydroxy-3-methoxybenzyl)propane-1,3-diamine；N,N'-Bis(2-hydroxy-3-methoxybenzyl)-1,3-diaminopropane；2-[[3-[(2-Hydroxy-3-methoxyphenyl)methylamino]propylamino]methyl]-6-methoxyphenol
• CAS: 5767-55-5
• 化学式: C₁₉H₂₆N₂O₄
• 分子量: 346.426
• InChiKey: OAUJEJBYBDLLAM-UHFFFAOYSA-N

物化性质

• 熔点：
  119-120 °C
• 沸点：
  519.8±50.0 °C(Predicted)
• 密度：
  1.174±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  25
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  83
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2,2'-[propane-1,3-diylbis(iminomethylene)]bis(6-methoxyphenol) 、 溴乙酸乙酯 在 potassium carbonate 作用下， 以 乙腈 为溶剂， 反应 24.0h， 以60%的产率得到diethyl-2,2'-(propane-1,3-diylbis((2-hydroxy-3-methoxybenzyl)azanediyl))diacetate
  参考文献：
  名称：

  Salen, reduced salen and N-alkylated salen type compounds: Spectral characterization, theoretical investigation and biological studies

  摘要：

  Salen [2,2'-{propane-1,3-diylbis[nitrilo(E)methylylidene]}bis(6-methoxyphenol)], reduced salen [(2,2'-[propane-1,3-diylbis(iminomethylene))]bis(6-methoxyphenol)] and N-alkylated salen [diethyl-2,2'-(propane-1,3-diylbis((2-hydroxy-3-methoxybenzyl) azanediyl))diacetate] compounds have been synthesized and characterized by IR, H-1 NMR, C-13 NMR and UV-vis. spectroscopy. Molecular geometry of the title compounds in the ground state has been optimized by density functional method (B3LYP) with 6-31G basis set. Vibrational frequencies of the compounds were computed and compared with the experimental values. Tautomeric stability study of salen inferred that the enolimine form is more stable than its keto-enamine form in gas phase. The spectral behavior of salen in polar and nonpolar solvents was examined demonstrate the positive solvatochromism. The synthesized compounds have been studied with respect to their binding to calf thymus DNA showed that there were interactions between the compounds and DNA through a groove binding mode. Furthermore, the DNA cleavage activity of the compounds has been investigated by gel electrophoresis. The antioxidant properties of compounds were evaluated by DPPH method. The N-alkylated compound has a higher DPPH free radical scavenging activity. The antimicrobial activity was investigated on various gram positive and gram negative bacteria. (C) 2012 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.saa.2012.11.100
• 作为产物：
  描述：

  N,N'-bis(3-methoxysalicylidene)-1,3-propanediamine 在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 生成 2,2'-[propane-1,3-diylbis(iminomethylene)]bis(6-methoxyphenol)
  参考文献：
  名称：

  四种含四齿仲二胺配体锌配合物固态结构中锂键、H 键和 π 堆积相互作用的重要性

  摘要：

  在这份手稿中，我们报告了四种新锌配合物的制备，[{(μ-CH 3 COO)ZnL 1 } 2 Zn]·2DMSO ( 1 ), [{(DMF)ZnL 1 (μ-CH 3 COO)ZnL 1 Zn(N 3 )}]·0.64DMSO·0.36EtOH ( 2 )、[(μ-CH 3 COO) 2 Zn 2 L 1 ] n ( 3 )和[Zn 2 L 2 Cl 2 ] ( 4 )及其通过元素和光谱分析表征，其中 H 2 L 1是1,3-丙二基双(亚氨基亚甲基)双(4-氯苯酚)并且H 2 L 2是1,3-丙二基双(亚氨基亚甲基)双(6-甲氧基苯酚)。该结构已通过单晶X射线衍射分析得到证实。复合物1和2的合成策略涉及使用 DMSO 滴，这对于分别稳定1和2的晶体至关重要，表明 DMSO 在稳定复合物中的重要性。使用分子中原子的量子理论和非共价相互作用图（NCI 图）进行的全面 DFT 计算表明在配合物1和2中形成了强氢键、CH⋯π

  DOI：

  10.1039/d2nj05490f

文献信息

• A benzoate bridged dinuclear mixed valence cobalt(III/II) complex with CoIIIO4CoII core: Synthesis, structure and investigation of its phenoxazinone synthase mimicking activity
  作者：Abhisek Banerjee、Shouvik Chattopadhyay

  DOI：10.1016/j.poly.2019.114290

  日期：2020.2

  Abstract A dinuclear class-I mixed valence cobalt(III)/cobalt(II) complex, [(N3)CoIIIL(µ-C6H5COO)CoII(N3)]·CH3OH [where H2L = (1,3-propanediyl)bis(iminomethylene)bis(6-methoxyphenol)] has been prepared and characterized by elemental and spectral analysis. The structure of the complex has been confirmed by single crystal X-ray diffraction analysis. The cobalt(III) center is placed in the inner N2O2

  摘要一种双核I类混合价钴（III）/钴（II）配合物，[（N3）CoIIIL（µ-C6H5COO）CoII（N3）]·CH3OH [其中H2L =（1,3-丙二基）双（亚氨基亚甲基） ）双（6-甲氧基苯酚）]已制备并通过元素分析和光谱分析表征。配合物的结构已通过单晶X射线衍射分析确认。钴（III）中心位于内部N2O2隔室中，而钴（II）中心位于配体的外部O4隔室中。该复合物可以充当活性官能模型，用于将k-cat = 153.90 h-1的2-氨基苯酚氧化为2-氨基苯恶嗪-3-酮。
• Study on interaction of <i>N</i>,<i>N</i>′-(2-hydroxy-3-methoxybenzyl) diamine cerium(IV) with bovine serum albumin
  作者：Hai-Tao Xia、Yu-Fen Liu、Wei-Xing Ma

  DOI：10.1080/00958972.2013.850496

  日期：2013.11.10

  Complexes of cerium(IV) with bis(N,N′-(2-hydroxy-3-methoxybenzyl) ethane-1,2-diamine, bis(2-hydroxy-3-methoxybenzyl) propane-1,2-diamine and bis(2-hydroxy-3-methoxybenzyl) propane-1,3-diamine were synthesized by reaction of cerium(IV) nitrate and the ligands. The obtained coordination compounds have also been characterized by elemental analysis, IR spectroscopy, and single crystal X-ray diffraction

  结合位点也根据 Stern-Volmer 方程获得，相应的热力学参数 ΔH、ΔS 和 ΔG 通过 van't Hoff 方程计算。氢键和范德华力是这些复合物和 BSA 之间的主要分子间作用力。BSA 与这些复合物之间的距离小于 8 nm，表明供体和受体之间的能量转移发生的概率很高。同步荧光研究表明，这些复合物与 BSA 的结合改变了酪氨酸残基周围的极性，而不是色氨酸残基。BSA 与这些复合物之间的距离小于 8 nm，表明供体和受体之间的能量转移发生的概率很高。同步荧光研究表明，这些复合物与 BSA 的结合改变了酪氨酸残基周围的极性，而不是色氨酸残基。BSA 与这些复合物之间的距离小于 8 nm，表明供体和受体之间的能量转移发生的概率很高。同步荧光研究表明，这些复合物与 BSA 的结合改变了酪氨酸残基周围的极性，而不是色氨酸残基。
• A series of hydrogen bond mediated dinuclear nickel(II) complexes with reduced Schiff base ligands: An insight into the nature of their short intermolecular hydrogen bonds
  作者：Saikat Mirdya、Michael G.B. Drew、Akash Kumar Chandra、Abhisek Banerjee、Antonio Frontera、Shouvik Chattopadhyay

  DOI：10.1016/j.poly.2020.114374

  日期：2020.3

  Abstract A series of isostructural centrosymmetric hydrogen bonded dimeric nickel(II) complexes of general formula, [Ni2(HL)2(DMSO)2(H2O)2]X where H2L = N2O4 donor reduced Schiff base ligand, [H2L1=(2,2-dimethyl-1,3-propanediyl)bis(iminomethylene)bis(6-methoxyphenol) and H2L2=(2,2-dimethyl-1,3-propanediyl)bis(iminomethylene)bis(6-ethoxyphenol)] and X = counter anion}, are synthesized and characterized

  摘要一系列[Ni2（HL）2（DMSO）2（H2O）2] X的同构中心对称氢键合二聚镍（II）配合物，其中H2L = N2O4供体还原的席夫碱配体，[H2L1 =（2 ，2-二甲基-1,3-丙二基）双（亚氨基亚甲基）双（6-甲氧基苯酚）和H2L2 =（2,2-二甲基-1,3-丙二基）双（亚氨基亚甲基）双（6-乙氧基苯酚）]和X合成，并通过元素分析，红外光谱和电子光谱进行表征。所有配合物的结构已通过单晶X射线衍射分析确认。每个配合物均以固态形式形成O⋯H⋯O氢键二聚体，其中O⋯O距离非常短，范围为2.424（3）至2.437（3）A。 DFT估计了这些氢键的能量。
• Field-induced single-molecule magnet behaviour in a series of dinuclear cobalt(III,II) complexes
  作者：Abhisek Banerjee、Carlos J. Gómez García、Samia Benmansour、Rosa M. Gomlia、Antonio Frontera、Shouvik Chattopadhyay

  DOI：10.1016/j.poly.2022.115802

  日期：2022.7

  crystal X-ray structures of complexes 1–4 show that both cobalt centres in the four complexes adopt a distorted octahedral geometry with Co(III) and Co(II) centres residing at inner N2O2 and outer O4 pockets of the reduced Schiff base, respectively. Magnetic measurements show that all complexes behave as Co(II) monomers, confirming the presence of diamagnetic low spin Co(III) ions, which have also been

  我们介绍了四种双核钴 (III,II) 配合物的合成、结构和磁性表征：[(NCS)Co III (L n )(µ–OAc)Co II (NCS)]·G，n/G = 1 /CH 3 OH ( 1 )、2/CH 3 CN ( 2 )、3/- ( 3 ) 和 4/CH 3 OH ( 4 )，即 H 2 L n，四种密切相关的还原席夫碱配体：H 2 L 1 = (1,3-丙二基)双(亚胺亚甲基)双(6-甲氧基苯酚), H 2 L 2 = (1,3-丙二基)双(亚胺亚甲基)双(6-乙氧基苯酚), H 2 L3 = (2,2-二甲基-1,3-丙二基)-双(亚胺亚甲基)双(6-甲氧基苯酚)和H 2 L 4 = (2,2-二甲基-1,3-丙二基)-双(亚胺亚甲基)双（6-乙氧基苯酚）。配合物1-4的单晶 X 射线结构表明，四个配合物中的钴中心均采用扭曲的八面体几何形状，Co(III) 和 Co(II) 中心位于内部
• The importance of spodium bonds, H-bonds and π-stacking interactions in the solid state structures of four zinc complexes with tetradentate secondary diamine ligands
  作者：Puspendu Middya、Mainak Karmakar、Rosa M. Gomila、Michael G. B. Drew、Antonio Frontera、Shouvik Chattopadhyay

  DOI：10.1039/d2nj05490f

  日期：——

  interaction plot (NCI plot) indicates the formation of strong H-bonds, CH⋯π and ancillary SpBs in complexes 1 and 2. DMSO has not been added during the synthesis of complexes 3 and 4, where no spodium bonds have been observed. Strong self-assembled (π–π stacked or H-bonded) dimers have been found in the solid state structures of 3 and 4.

  在这份手稿中，我们报告了四种新锌配合物的制备，[(μ-CH 3 COO)ZnL 1 } 2 Zn]·2DMSO ( 1 ), [(DMF)ZnL 1 (μ-CH 3 COO)ZnL 1 Zn(N 3 )}]·0.64DMSO·0.36EtOH ( 2 )、[(μ-CH 3 COO) 2 Zn 2 L 1 ] n ( 3 )和[Zn 2 L 2 Cl 2 ] ( 4 )及其通过元素和光谱分析表征，其中 H 2 L 1是1,3-丙二基双(亚氨基亚甲基)双(4-氯苯酚)并且H 2 L 2是1,3-丙二基双(亚氨基亚甲基)双(6-甲氧基苯酚)。该结构已通过单晶X射线衍射分析得到证实。复合物1和2的合成策略涉及使用 DMSO 滴，这对于分别稳定1和2的晶体至关重要，表明 DMSO 在稳定复合物中的重要性。使用分子中原子的量子理论和非共价相互作用图（NCI 图）进行的全面 DFT 计算表明在配合物1和2中形成了强氢键、CH⋯π