2,4-Ditert-butyl-6-[(quinolin-8-ylamino)methyl]phenol | 800393-58-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 2,4-Ditert-butyl-6-[(quinolin-8-ylamino)methyl]phenol
• 英文别名: 2,4-ditert-butyl-6-[(quinolin-8-ylamino)methyl]phenol
• CAS: 800393-58-2
• 化学式: C₂₄H₃₀N₂O
• 分子量: 362.515
• InChiKey: AVWPQOLOWITMPT-UHFFFAOYSA-N

物化性质

• 沸点：
  479.7±40.0 °C(Predicted)
• 密度：
  1.102±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.7
• 重原子数：
  27
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  45.2
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  [Yb(bis(trimethylsilyl)amido)3(μ-Cl)Li(tetrahydrofuran)3] 、 2,4-Ditert-butyl-6-[(quinolin-8-ylamino)methyl]phenol 以 四氢呋喃 为溶剂， 反应 24.0h， 以70%的产率得到
  参考文献：
  名称：

  Synthesis and characterization of lanthanide amides bearing phenoxy(quinolinyl)amide ligand and their application in the ring-opening polymerization of 1,4-dioxan-2-one

  摘要：

  The amine elimination reaction of quinolinyl aminophenol (LH2) with Ln[N(SiMe3)(2)](3)(mu-Cl)Li(THF)(3) in THF afforded lanthanide-lithium aminophenoxy complexes L(2)LnLi(THF)(2) (Ln = Yb (1), Sm (2)), while the similar reaction with Ln[N(SiMe3)(2)](3) in toluene gave normal monoamido lanthanide complexes LLnN(SiMe3)(2)(DME) (Ln = Sm (3), Nd (4), La (5)). All complexes have been fully characterized. X-ray structural determination revealed that complexes 1 and 2 have a monomeric C-2-symmetric hetero-bimetallic structure, in which the lanthanide atom is connected to the lithium atom by two oxygen bridges from two phenoxy(quinolinyl) amide ligands. Complexes 4 and 5 have a solvated monomeric structure, and the lanthanide metal centers adopt a distorted octahedral geometry. It was found that complexes 3-5 initiated the ring-opening polymerization of 1,4-dioxan-2-one (PDO) with high activity. (C) 2014 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jorganchem.2014.04.017
• 作为产物：
  描述：

  8-氨基喹啉 、 3,5-二叔丁基水杨醛 在 甲酸 作用下， 以 甲醇 为溶剂， 反应 12.0h， 生成 2,4-Ditert-butyl-6-[(quinolin-8-ylamino)methyl]phenol
  参考文献：
  名称：

  Rare Self-Luminous Mixed-Valence Eu-MOF with a Self-Enhanced Characteristic as a Near-Infrared Fluorescent ECL Probe for Nondestructive Immunodetection

  摘要：

  通过一种罕见的混合电价 Eu-MOF（L4EuIII2EuII），可以实现 Eu2+ 对 Eu3+ 的稳定而高效的敏化发射。与其他物质的敏化相比，Eu2+ 和 Eu3+ 之间相似的离子半径和核外电子构型使敏化更容易、更高效。Eu2+ 对 Eu3+ 的敏化对 L4EuIII2EuII 的自增强发光、更长的发光时间和更稳定的电化学发光（ECL）信号有很大帮助。同时，L4EuIII2EuII 具有约 900 纳米的近红外荧光和强大的自发光特性，可用作近红外荧光探针和发光体，以建立近红外 ECL 生物传感器。这种近红外生物传感器凭借近红外的强敏感性和环境适应性，可以大大减少对被检测样品的破坏，甚至实现无损检测，提高检测灵敏度。此外，由于 Ce3+/Ce4+ 和 Co2+/Co3+ 两种氧化还原对的作用，CeO2@Co3O4 三壳微球进一步增强了 ECL 强度。基于这些策略的近红外 ECL 生物传感器对 CYFRA 21-1 具有超灵敏的检测能力，检出限低至 1.70 fg/mL，同时也为构建高效无损的免疫检测生物传感器提供了新的思路。

  DOI：

  10.1021/acs.analchem.1c01531

文献信息

• Synthesis and Structural Characterization of Mixed-Valent Ytterbium and Europium Complexes Supported by a Phenoxy(quinolinyl)amide Ligand
  作者：Yinyin Jiang、Xi Zhu、Muzi Chen、Yaorong Wang、Yingming Yao、Bing Wu、Qi Shen

  DOI：10.1021/om5000198

  日期：2014.4.28

  mixed-valent ytterbium and europium complexes L4LnIII2LnII (Ln = Yb (1), Eu (2)) was observed for the first time in the spontaneous reduction reaction system of quinolinyl aminophenol (H2L) with Ln[N(SiMe3)2]3 (Ln = Yb, Eu) in toluene at 90 °C, whereas the same reaction with Sm[N(SiMe3)2]3 gave the expected monoamido samarium complex LSmN(SiMe3)2(DME) (4). The isolation of the binuclear ytterbium complex L3Yb2

  在喹啉基氨基酚（H 2 L）的自发还原反应体系中首次观察到mixed和-的混合价络合物L 4 Ln III 2 Ln II（Ln = Yb（1），Eu（2））的形成。在90°C下与Ln [N（SiMe 3）2 ] 3（Ln = Yb，Eu）在甲苯中反应，而与Sm [N（SiMe 3）2 ] 3的相同反应得到预期的单酰胺do络合物LSmN（SiMe 3）2（DME）（4）。双核y复合物L 3的分离Yb 2（3）在温和的条件下表明，从三价配合物到混合价species物种1的转变可能涉及配体再分布反应和Yb–N键的均质化。
• Synthesis and characterization of lanthanide amides bearing phenoxy(quinolinyl)amide ligand and their application in the ring-opening polymerization of 1,4-dioxan-2-one
  作者：Hairong Zhou、Yinyin Jiang、Muzi Chen、Yaorong Wang、Yingming Yao、Bing Wu、Dongmei Cui

  DOI：10.1016/j.jorganchem.2014.04.017

  日期：2014.8

  The amine elimination reaction of quinolinyl aminophenol (LH2) with Ln[N(SiMe3)(2)](3)(mu-Cl)Li(THF)(3) in THF afforded lanthanide-lithium aminophenoxy complexes L(2)LnLi(THF)(2) (Ln = Yb (1), Sm (2)), while the similar reaction with Ln[N(SiMe3)(2)](3) in toluene gave normal monoamido lanthanide complexes LLnN(SiMe3)(2)(DME) (Ln = Sm (3), Nd (4), La (5)). All complexes have been fully characterized. X-ray structural determination revealed that complexes 1 and 2 have a monomeric C-2-symmetric hetero-bimetallic structure, in which the lanthanide atom is connected to the lithium atom by two oxygen bridges from two phenoxy(quinolinyl) amide ligands. Complexes 4 and 5 have a solvated monomeric structure, and the lanthanide metal centers adopt a distorted octahedral geometry. It was found that complexes 3-5 initiated the ring-opening polymerization of 1,4-dioxan-2-one (PDO) with high activity. (C) 2014 Elsevier B.V. All rights reserved.
• Rare Self-Luminous Mixed-Valence Eu-MOF with a Self-Enhanced Characteristic as a Near-Infrared Fluorescent ECL Probe for Nondestructive Immunodetection
  作者：Lu Zhao、Xianzhen Song、Xiang Ren、Dawei Fan、Qin Wei、Dan Wu

  DOI：10.1021/acs.analchem.1c01531

  日期：2021.6.22

  Steady and efficient sensitized emission of Eu2+ to Eu3+ can be achieved through a rare mixed-valence Eu-MOF (L4EuIII2EuII). Compared with the sensitization of other substances, the similar ion radius and configuration of the extranuclear electron between Eu2+ and Eu3+ make sensitization easier and more efficient. The sensitization of Eu2+ to Eu3+ is of great assistance for the self-enhanced luminescence of L4EuIII2EuII, the longer luminous time, and the more stable electrochemiluminescence (ECL) signal. Simultaneously, L4EuIII2EuII possesses near-infrared (NIR) fluorescence of around 900 nm and a mighty self-luminous characteristic, which render it useful as a NIR fluorescent probe and as a luminophore to establish a NIR ECL biosensor. This NIR biosensor can greatly reduce the damage to the detected samples and even achieve a nondestructive test and improve the detection sensitivity by virtue of strong susceptibility and environmental suitability of NIR. In addition, the CeO2@Co3O4 triple-shelled microspheres further enhanced the ECL intensity due to two redox pairs of Ce3+/Ce4+ and Co2+/Co3+. The NIR ECL biosensor based on these strategies owns an ultrasensitive detection ability of CYFRA 21-1 with a low limit of detection of 1.70 fg/mL and also provides a novel idea for the construction of a highly effective nondestructive immunodetection biosensor.

  通过一种罕见的混合电价 Eu-MOF（L4EuIII2EuII），可以实现 Eu2+ 对 Eu3+ 的稳定而高效的敏化发射。与其他物质的敏化相比，Eu2+ 和 Eu3+ 之间相似的离子半径和核外电子构型使敏化更容易、更高效。Eu2+ 对 Eu3+ 的敏化对 L4EuIII2EuII 的自增强发光、更长的发光时间和更稳定的电化学发光（ECL）信号有很大帮助。同时，L4EuIII2EuII 具有约 900 纳米的近红外荧光和强大的自发光特性，可用作近红外荧光探针和发光体，以建立近红外 ECL 生物传感器。这种近红外生物传感器凭借近红外的强敏感性和环境适应性，可以大大减少对被检测样品的破坏，甚至实现无损检测，提高检测灵敏度。此外，由于 Ce3+/Ce4+ 和 Co2+/Co3+ 两种氧化还原对的作用，CeO2@Co3O4 三壳微球进一步增强了 ECL 强度。基于这些策略的近红外 ECL 生物传感器对 CYFRA 21-1 具有超灵敏的检测能力，检出限低至 1.70 fg/mL，同时也为构建高效无损的免疫检测生物传感器提供了新的思路。