2,6-bis((1H-1,2,4-triazol-1-yl)methyl)-4-methylphenol | 845255-47-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 2,6-bis((1H-1,2,4-triazol-1-yl)methyl)-4-methylphenol
• 英文别名: 4-Methyl-2,6-bis(1,2,4-triazol-1-ylmethyl)phenol；4-methyl-2,6-bis(1,2,4-triazol-1-ylmethyl)phenol
• CAS: 845255-47-2
• 化学式: C₁₃H₁₄N₆O
• 分子量: 270.294
• InChiKey: FROFBKCQMDRXFI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  81.6
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2,6-bis((1H-1,2,4-triazol-1-yl)methyl)-4-methylphenol 、 5,6-二氯-2,3-二氰基吡嗪 在 吡啶 作用下， 以 丙酮 为溶剂， 反应 24.0h， 以90%的产率得到5,6-bis{2,6-bis[(1H-1,2,4-triazol-1-yl)methyl]-4-methylphenoxy}-pyrazine-2,3-dicarbonitrile
  参考文献：
  名称：

  Phthalocyanines and Tetrapyrazinoporphyrazines with Two Cationic Donuts: High Photodynamic Activity as a Result of Rigid Spatial Arrangement of Peripheral Substituents

  摘要：

  High photodynamic activity was observed for hexadeca-cationic zinc, magnesium, and metal-free phthalocyanines (Pcs) and tetrapyrazinoporphyrazines with EC50 values as low as 5 nM (MCF-7 cells) for the best compound; this activity was several times better than that of clinically established photosensitizers verteporfin, temoporfin, S3AlOHPc, or protoporphyrin IX. This lead compound was characterized by low dark toxicity (TC50 = 369 mu M), high efficiency against other cell lines (HCT 116 and HeLa), and possible activation by light above 680 nm. The excellent photodynamic activity resulted from the rigid spatial arrangement of the quaternized triazole moieties above and below the Pc core, as confirmed by X-ray crystallography. The triazole moieties thus formed two "cationic donuts" that protected the hydrophobic core against aggregation in water. The lysosoines were found to be the site of subcellular localization and were consequently the primary targets of photodynamic injury, resulting in predominantly necrotic cell death.

  DOI：

  10.1021/acs.jmedchem.7b00272
• 作为产物：
  描述：

  对甲酚 以 1,4-二氧六环 为溶剂， 反应 5.0h， 生成 2,6-bis((1H-1,2,4-triazol-1-yl)methyl)-4-methylphenol
  参考文献：
  名称：

  使用 2,6-Di(1H-1,2,4-三唑-1-基-甲基)-4-R-苯氧基配体调节同金属 DyIII、TbIII 和 EuIII 1-D 配位聚合物的发射：通过单态

  摘要：

  这项工作报告了具有两个苯氧三唑基配体的 Dy III、Tb III和 Eu III配位聚合物的结构表征和光物理性质[2,6-di(1 H -1,2,4-trizo-1-yl) -甲基)-4-R-苯氧基，L R Tr (R = CH 3；Cl)]。这些配体使我们能够获得同构聚合物，被描述为一维双链，其中 Ln III是九配位的。使用 Y III类似物的低温时间分辨发射光谱估算了配体三重态 (T 1 ) 态的能量。具有 L Cl Tr 的化合物比具有 L Me Tr 的化合物具有更高的发射强度。Tb III化合物的发射不受所使用的不同激发波长的影响，并且在纯绿光区域发射。相比之下，DyL Me Tr在蓝到白区域发射光，而DyL Cl Tr在所有激发波长下都保持在白色区域。另一方面，Eu III化合物在蓝色（配体）或红色区域（Eu III）发光，具体取决于苯氧部分的取代基和激发波长。通过使用时间

  DOI：

  10.1021/acs.inorgchem.3c02201

文献信息

• Exceptionally effective generation of singlet oxygen in aqueous media via iodinated zinc-phthalocyanine
  作者：Basma Ghazal、Ali Husain、Asaithampi Ganesan、Mahmut Durmuş、Xian-Fu Zhang、Saad Makhseed

  DOI：10.1016/j.dyepig.2019.01.036

  日期：2019.5

  heavy metal atom have been investigated as singlet oxygen generators in aqueous media. In addition to the heavy atom effect exerted by iodine covalently bonded to the Pc molecule, a second dimensional effect induced by aggregation which brings the iodine anions of triazolyl units into closer proximity to the Pc core leading to the highest reported singlet oxygen generation for a Pc derivative in water

  已经研究了具有季铵化三唑基部分的不对称取代锌酞菁（Pc）衍生物的水溶性和碘作为重金属原子作为水性介质中的单重态氧产生剂。除了碘与Pc分子共价结合产生的重原子效应外，聚集引起的二维效应还使三唑基单元的碘阴离子更靠近Pc核，从而导致Pc的单线态氧生成量最高在水衍生物（Φ Δ  = 0.87）。
• Purple subphthalocyanine‐phthalocyanine dyad: Synthesis, photophysicochemical properties and DFT study
  作者：Saad Makhseed、Basma Ghazal、Mahmut Durmuş

  DOI：10.1002/aoc.5780

  日期：2020.9

  A new phthalocyanine‐subphthalocyanine heterodyad (5) was prepared by Pd(0)‐catalyzed Sonogashira coupling reaction between an asymmetrical phthalocyanine (3) bearing monoiodo and multiple triazolide moieties on its backbone and a subphthalocyanine (4) bearing axially propargyl group. The structure of this heterodyad (5) was subsequently confirmed by the conventional spectroscopic techniques. The photophysical

  通过Pd（0）催化的Sonogashira偶联反应制备了一种新的酞菁-亚酞菁亚杂二酮（5），该不对称酞菁（3）带有单碘和其主链上的多个三偶氮基部分与一个亚酞菁（4）带有轴向炔丙基。随后通过常规的光谱技术确认了该杂双（5）的结构。光物理和光化学特性包括：（5）及其建筑生色团（3）和（4）的荧光和单态氧的产生。）也进行了调查。有趣的是，这种新型双染料观察到了紫色溶液，与酞菁-亚酞菁共轭物获得的颜色（绿色或蓝色）明显不同。根据稳态吸收光谱数据和瞬态吸收结果，合成的二元组5没有聚集，并且在Pc和subPc部分之间发生了良好的能量转移。使用密度泛函理论（DFT）和时变DFT（TDDFT）分析证实了这一结果：B3LYP交换相关函数和6–31 + G（d）基础集。
• A novel coordination polymer constructed from 1D neutral chains via inter-chain π–π stacking and hydrogen bonding
  作者：Haibin Zhu、Chunhui Huang、Wei Huang、Shaohua Gou

  DOI：10.1016/j.inoche.2004.08.003

  日期：2004.10

  A novel 1D neutral coordination polymer, [Cu(dtmp)(dmf)Cl-2]dmf}(n) (1) (dtmp = 1,6-di(triazole-1-yl-methyl)-4-methylphenol, dmf = dimethyl formamide) was synthesized by reacting CuCl2 (.) 2H(2)O with the dtmp ligand. The crystal and molecular structure of the complex was determined by X-ray diffraction, in which the coordination geometry around the copper center is slightly distorted trigonal bypyramidal. One-dimensional chains have been formed through the metal and the ligand via coordination bonds, which are assembled further into a two-dimensional network by inter-chain synergic pi-pi stacking and hydrogen bonding. (C) 2004 Elsevier B.V. All rights reserved.
• Phthalocyanines and Tetrapyrazinoporphyrazines with Two Cationic Donuts: High Photodynamic Activity as a Result of Rigid Spatial Arrangement of Peripheral Substituents
  作者：Basma Ghazal、Miloslav Machacek、Mona Abbas Shalaby、Veronika Novakova、Petr Zimcik、Saad Makhseed

  DOI：10.1021/acs.jmedchem.7b00272

  日期：2017.7.27

  High photodynamic activity was observed for hexadeca-cationic zinc, magnesium, and metal-free phthalocyanines (Pcs) and tetrapyrazinoporphyrazines with EC50 values as low as 5 nM (MCF-7 cells) for the best compound; this activity was several times better than that of clinically established photosensitizers verteporfin, temoporfin, S3AlOHPc, or protoporphyrin IX. This lead compound was characterized by low dark toxicity (TC50 = 369 mu M), high efficiency against other cell lines (HCT 116 and HeLa), and possible activation by light above 680 nm. The excellent photodynamic activity resulted from the rigid spatial arrangement of the quaternized triazole moieties above and below the Pc core, as confirmed by X-ray crystallography. The triazole moieties thus formed two "cationic donuts" that protected the hydrophobic core against aggregation in water. The lysosoines were found to be the site of subcellular localization and were consequently the primary targets of photodynamic injury, resulting in predominantly necrotic cell death.
• Tuning the Emission of Homometallic Dy^III, Tb^III, and Eu^III 1-D Coordination Polymers with 2,6-Di(1<i>H</i>-1,2,4-triazole-1-yl-methyl)-4-R-phenoxo Ligands: Sensitization through the Singlet State
  作者：Jorge Manzur、Pablo Fuentealba、Yolimar Gil、Juliana Pérez-Obando、Jeannette Morales Alfaro、Andrés Igor Vega Carvallo、Daniel Aravena、Ricardo Costa de Santana、Albano N. Carneiro Neto、Evgenia Spodine

  DOI：10.1021/acs.inorgchem.3c02201

  日期：2023.11.27

  a 1D double chain, with LnIII being nona-coordinated. The energies of the ligand triplet (T1) states were estimated using low-temperature time-resolved emission spectra of YIII analogues. Compounds with LClTr present higher emission intensity than those with LMeTr. The emission of TbIII compounds was not affected by the different excitation wavelengths used and was emitted in the pure green region

  这项工作报告了具有两个苯氧三唑基配体的 Dy III、Tb III和 Eu III配位聚合物的结构表征和光物理性质[2,6-di(1 H -1,2,4-trizo-1-yl) -甲基)-4-R-苯氧基，L R Tr (R = CH 3；Cl)]。这些配体使我们能够获得同构聚合物，被描述为一维双链，其中 Ln III是九配位的。使用 Y III类似物的低温时间分辨发射光谱估算了配体三重态 (T 1 ) 态的能量。具有 L Cl Tr 的化合物比具有 L Me Tr 的化合物具有更高的发射强度。Tb III化合物的发射不受所使用的不同激发波长的影响，并且在纯绿光区域发射。相比之下，DyL Me Tr在蓝到白区域发射光，而DyL Cl Tr在所有激发波长下都保持在白色区域。另一方面，Eu III化合物在蓝色（配体）或红色区域（Eu III）发光，具体取决于苯氧部分的取代基和激发波长。通过使用时间