2,2'-(((azanediylbis(propane-3,1-diyl))bis(azanylylidene))bis(methanylylidene))diphenol | 52279-45-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 2,2'-(((azanediylbis(propane-3,1-diyl))bis(azanylylidene))bis(methanylylidene))diphenol
• 英文别名: bis(salicylidenimino-3-propyl)amine；Phenol,2,2'-[iminobis(3,1-propanediylnitrilomethylidyne)]bis-；2-[3-[3-[(2-hydroxyphenyl)methylideneamino]propylamino]propyliminomethyl]phenol
• CAS: 52279-45-5
• 化学式: C₂₀H₂₅N₃O₂
• 分子量: 339.437
• InChiKey: PHYCNXXYJSMREF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  25
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  77.2
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2,2'-(((azanediylbis(propane-3,1-diyl))bis(azanylylidene))bis(methanylylidene))diphenol 在 potassium carbonate 作用下， 以 四氢呋喃 为溶剂， 反应 24.0h， 生成 Mn[salicylaldehyde(3-iodopropyl trimethoxysilane)bis(aminopropyl)amine]
  参考文献：
  名称：

  Synthesis and application of FeIII, NiII and MnII complexes anchored to HMS as efficient catalysts for cycloalkane oxyfunctionalization

  摘要：

  Methoxysilane Schiff-base pentacoordinate metal complexes, Le. Fe[Sal(PMeO-Si)DPTA], Ni[Sal(PMeO-Si)DPTA] and Mn[Sal(PMeO-Si)DPTA], were synthesized and single site covalently anchored into the uniform porous texture of HMS (2-10 nm size) via condensation process. The correspondent supported catalysts (4.a, 4.b and 4.c, respectively) were characterized by FT-IR, SEM/EDS, XRD, TG, EPR and AAS analysis. In the catalytic tests, they showed high efficiency in the selective oxidation of cyclohexane using molecular O-2 (overall conversion 40.7% with Cat. 4.a, 29.5% with Cat. 4.b and 26.2% with Cat. 4.c) under relatively mild condition in batch reactor. The Cat.4.a system (HMS/3.a) exhibits highest TONs ca. 4.2 x 10(3) with good selectivity ca. 70% (48% ketone selectivity). The reaction mechanism involves free radicals, as it was proved by the addition of PPh3. Finally, these supported catalysts could be reuse up to several catalytic cycles. (C) 2013 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.molcata.2013.12.004
• 作为产物：
  描述：

  3,3'-二氨基二丙基胺 、 水杨醛 以 氯仿 为溶剂， 反应 1.0h， 生成 2,2'-(((azanediylbis(propane-3,1-diyl))bis(azanylylidene))bis(methanylylidene))diphenol
  参考文献：
  名称：

  氯化镍 (II) 希夫碱络合物：合成、表征、毒性、抗菌和杀利什曼原虫活性

  摘要：

  使用希夫碱复合物对抗微生物制剂 a 最近作为一种对抗由多重耐药细菌和利什曼原虫引起的感染的策略受到了更多关注。本研究旨在评估氯化镍 (II) 席夫碱复合物 ([Ni(L2)] 对Leishmania amazonensis promastigote、多重耐药菌株的毒性、抗菌和杀利什曼原虫活性，并评估调节抗生素活性对抗多重耐药细菌. 席夫碱配合物通过元素分析、傅里叶变换红外光谱 (FTIR)、紫外-可见吸收光谱和热分析 (TGA/DTG/DSC) 技术表征。[Ni(L2)] 配合物在盐水卤虫（LC 50 = 150.8 微克/毫升）。在利什曼原虫测定中，NiL2 复合物显示的 IC 50值为 (6.079 μg/mL ± 0.05656 在 24 小时)、(0.854 μg/mL ± 0.02474, 48 h) 和 (1.076 μg/mL ± 0.04039, 72)。在抗菌试验中，[Ni(L2)]

  DOI：

  10.1016/j.cbi.2021.109714

文献信息

• Synthesis and characterization of 5- and 7-donor Schiff base ligands and spectroscopic evidence for tautomerism: A crystal structure showing tautomeric forms within one ligand
  作者：Hezron F.O. Ogutu、Waheed Saban、Rehana Malgas-Enus、Robert C. Luckay

  DOI：10.1016/j.molstruc.2019.02.054

  日期：2019.6

  Abstract An improved method for the synthesis of fifteen Schiff base ligands, of which six are novel, are reported. Optimised yields were obtained and the ligands have been fully characterized via several analytical techniques. It was found that tautomeric forms of these novel ligands exist and spectroscopic evidence for this phenomenon is provided. A crystal structure illustrating both enol and keto tautomeric

  摘要 报道了一种合成 15 种席夫碱配体的改进方法，其中 6 种是新的。获得了优化的产量，并通过多种分析技术充分表征了配体。发现存在这些新配体的互变异构形式，并提供了这种现象的光谱证据。说明新配体中烯醇和酮互变异构形式的晶体结构补充了获得的光谱证据。据我们所知，这是同一配体中互变异构形式的首次报道证据。
• Crystal Structures, Optical Properties, and TD-DFT Study of a Zinc(II) Schiff-Base Complex Derived from Salicylaldehyde and N1-(3-aminopropyl)Propane-1,3-Diamine
  作者：Murad A. AlDamen、Noureddine Charef、Hassan K. Juwhari、Kamal Sweidan、Mohammad S. Mubarak、Dennis G. Peters

  DOI：10.1007/s10870-016-0670-y

  日期：2016.12

  A zinc(II) complex of the pentadentate Schiff base ligand 2,2′(((azanediylbis(propane-3,1-diyl))bis(azanylylidene))bis(methanylylidene))diphenol was synthesized by reaction of the ligand with Zn(OAc)2. Reaction of salicylaldehyde with N1-(3-aminopropyl)propane-1,3-diamine [HN(C3H6NH2)2] in absolute ethanol was used to prepare the ligand. Non-merohedrally twinned crystals of the complex were characterized by single-crystal XRD and found to be in the monoclinic system, space group P21/n, with the following lattice parameters: a = 14.6594(8) Å, b = 11.6908(7) Å, c = 23.2789(14) Å, and β = 105.520(3)°. Luminescent characteristics of this complex were investigated in the solid state. Computational study of the electronic properties of this complex with the aid of time-dependent density functional theory (TD-DFT) showed good agreement with experimental data and hence consolidated the assignment of the state as ligand centered charge transfer. This complex exhibits a strong fluorescence with a broad blue emission maximum centered at 442 nm.

  通过配体与 Zn(OAc)2 的反应，合成了五价席夫碱配体 2,2′(((偶氮二基双(丙烷-3,1-二基))双(偶氮亚乙基))双(甲基亚乙基))二酚的锌(II)配合物。水杨醛与 N1-(3-氨基丙基)丙烷-1,3-二胺[HN(C3H6NH2)2]在绝对乙醇中的反应被用来制备配体。通过单晶 X 射线衍射表征，发现该配合物为单斜晶系，空间群为 P21/n，晶格参数如下：a = 14.6594(8) Å，b = 11.6908(7) Å，c = 23.2789(14) Å，β = 105.520(3)°。研究了该复合物在固态下的发光特性。借助时间相关密度泛函理论（TD-DFT）对该复合物的电子特性进行的计算研究表明，该复合物的电子特性与实验数据十分吻合，从而巩固了以配体为中心的电荷转移状态。该复合物具有很强的荧光，在 442 纳米波长处有一个宽广的蓝色发射最大值。
• Functionalization of Gold Nanoparticles by Iron(III) Complexes Derived from Schiff Base Ligands
  作者：Cédric R. Mayer、Gregory Cucchiaro、Josseline Jullien、Frédéric Dumur、Jérôme Marrot、Eddy Dumas、Francis Sécheresse

  DOI：10.1002/ejic.200800227

  日期：2008.8

  A series of iron(III) complexes derived from a variety of pentadentate Schiff base ligands, namely salten [H2salten = bis(3-salicylideneaminopropyl)amine] derivatives, have been synthesized and further used to stabilize and functionalize gold nanoparticles (Au-NPs). The iron complexes have been specifically designed to interact with the Au-NPs through an ambidentate thiocyanate ligand or through a

  已经合成了一系列源自各种五齿席夫碱配体的铁 (III) 配合物，即盐酸盐 [H2salten = 双（3-水杨基氨基丙基）胺] 衍生物，并进一步用于稳定和功能化金纳米粒子 (Au-NPs) . 铁配合物经过专门设计，可通过双齿硫氰酸酯配体或通过盐衍生物配体携带的硫醇侧基与 Au-NP 相互作用。金纳米复合材料是通过在铁配合物存在下直接还原 AuIII 或通过预官能化金纳米颗粒上的配位化学合成的。在后一种情况下，带有悬垂空盐笼的 Au-NP 已用 FeIII 处理以生成铁配合物。空间和静电排斥已被调整以获得稳定的胶体溶液或诱导金纳米复合材料的沉淀。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2008)
• X-Ray crystal structures of copper(<scp>ii</scp>) and cobalt(<scp>ii</scp>) complexes with Schiff base ligands. Reactivity towards dioxygen
  作者：Francis Carré、Robert J. P. Corriu、Emmanuelle Lancelle-Beltran、Ahmad Mehdi、Catherine Reyé、Roger Guilard、Jan Sýkora、Arie van der Lee

  DOI：10.1039/b304032a

  日期：——

  Copper(II) and cobalt(II) Schiff base complexes with derivatives of the pentadentate ligand bis(salicylideneimino-3-propyl)amine [H2salDPT] have been prepared. The X-ray crystal structures of the copper(II) complexes Cu[salDPT] and Cu[sal(n-propyltrimethylsilyl)DPT] were determined and revealed five-coordination at the metal centre in both cases. The 1 ∶ 1 dioxygen adduct of Co[sal(n-propyltrimethylsilyl)DPT]

  带有五齿衍生物的铜（II）和钴（II）Schiff碱配合物配体已经制备了双（水杨亚氨基亚氨基-3-丙基）胺[H 2 salDPT]。确定了铜（II）配合物Cu [salDPT]和Cu [sal（n-丙基三甲基甲硅烷基）DPT]的X射线晶体结构，两种情况下在金属中心均显示出五配位。还分离了Co [sal（n-丙基三甲基甲硅烷基）DPT]的1：1双氧加合物，并确定了其X射线分子结构。
• Process and apparatus for producing ketoisophorone
  申请人：Daicel Chemical Industries,Ltd.

  公开号：US20020055657A1

  公开（公告）日：2002-05-09

  &bgr;-isophorone is formed by isomerizing &agr;-isophorone in the presence of an isomerizing catalyst (an aliphatic C 5-20 polycarboxylic acid) in an isomerizing-reaction unit 1. The &bgr;-isophorone thus formed is oxidized with oxygen in an inert solvent in the presence of an oxidizing catalyst (a complex salt of a transition metal and an N,N′-disalicylidenediamine) in an oxidizing-reaction unit 2, thereby forming ketoisophorone. After removing a low-boiling point component, which is an impurity (non-conjugated cyclic ketone), from the reaction mixture using a distilling unit 3, a high-boiling component (oxidizing catalyst) is separated in a distilling unit 4 , and then ketoisophorone is separated from the solvent in the separation unit 5. Thereafter, the solvent containing 0 to 5,000 ppm (weight basis) of the impurities and substantially free from ketoisophorone is recycled to the oxidizing reaction through a recycling line 6. According to the present invention, the combination of the isomerizing reaction and the oxidizing reaction makes it possible to produce ketoisophorone from &agr;-isophorone while maintaining the activity of the oxidizing catalyst.

  &bgr;-异佛尔酮是通过在异构化反应装置1中，在异构化催化剂（脂肪族C5-20多羧酸）的存在下，将&agr;-异佛尔酮异构化形成的。然后，在氧化反应装置2中，在氧化催化剂（过渡金属的复杂盐和N，N'-二水杨基二胺）的存在下，将&Bgr;-异佛尔酮与氧气在惰性溶剂中氧化，从而形成酮异佛尔酮。使用蒸馏装置3从反应混合物中去除低沸点成分（非共轭环状酮）作为杂质后，使用蒸馏装置4分离高沸点成分（氧化催化剂），然后使用分离装置5从溶剂中分离出酮异佛尔酮。此后，含有0至5,000 ppm（重量基础）杂质且基本不含酮异佛尔酮的溶剂通过回收线6循环到氧化反应中。根据本发明，异构化反应和氧化反应的组合使得能够在保持氧化催化剂活性的同时从&agr;-异佛尔酮中生产酮异佛尔酮。