bis-pyridin-2-ylmethyl-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-phenyl]-amine | 1203669-57-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: bis-pyridin-2-ylmethyl-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-phenyl]-amine
• 英文别名: bis(pyridin-2-ylmethyl)[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]amine；N,N-bis(pyridin-2-ylmethyl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline；bis-pyridin-2-ylmethyl[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]amine
• CAS: 1203669-57-1
• 化学式: C₂₄H₂₈BN₃O₂
• 分子量: 401.316
• InChiKey: GWBUJXJZTCDLEQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.98
• 重原子数：
  30.0
• 可旋转键数：
  6.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  47.48
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  bis-pyridin-2-ylmethyl-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-phenyl]-amine 在 双氧水 、 sodium hydroxide 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 生成 N,N-bis(pyridin-2-ylmethyl)aniline
  参考文献：
  名称：

  Protic media enhanced protodeboronation for a potential H2O2-sensitive ligand system

  摘要：

  The detection of elevated concentrations of reactive oxygen species (ROS) such as H2O2 represents a promising route to identify oxidative misregulation in cells, a hallmark of carcinoma and neurodegeneration. Magnetic resonance imaging (MRI) presents an opportunity to detect ROS over a greater portion of the body compared to strategies such as fluorescence. To sense hydrogen peroxide, potential Fe2+ and Co2+ MRI sensors were synthesized by appending pinacolborane to two amino-pyridine ligand scaffolds. These were designed to expose phenol upon reaction with H2O2, turning on PARACEST (Paramagnetic Chemical Exchange Saturation Transfer) and allowing detection by MRI. Instead of yielding a phenol upon exposure to oxidative conditions, protodeboronation was observed as the major product even under mild conditions. Optimization of oxidation conditions allowed access to the phenolic analogue of the two ligands studied in 11% and 17% conversion under organic conditions. Treatment of the Fe2+ and Co2+ complexes with H2O2 resulted in rapid, partial demetallation with no evidence of the bound or free ligand undergoing an oxidative transformation. These results stress the importance of establishing stability of potential MRI contrast agents in aqueous conditions. (C) 2020 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.poly.2020.114377
• 作为产物：
  描述：

  对碘苯胺 在 potassium tert-butylate 、 potassium acetate 、 palladium diacetate 、 三苯基膦 作用下， 以 水 、 二甲基亚砜 为溶剂， 反应 114.0h， 生成 bis-pyridin-2-ylmethyl-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-phenyl]-amine
  参考文献：
  名称：

  基于 Azulene 的二磷酸腺苷荧光化学传感器

  摘要：

  AzuFluor® 435-DPA-Zn 是一种带有两个锌 ( II )-二吡啶甲胺受体基序的芴烯荧光团，在二磷酸腺苷存在下表现出荧光增强。ADP 对 ATP、AMP 和 PPi 的选择性源于受体基序的适当定位，因为异构传感器不能区分 ADP 和 ATP。

  DOI：

  10.1039/d1cc04122c

文献信息

• Quantifying factors that influence metal ion release in photocaged complexes using ZinCast derivatives
  作者：Celina Gwizdala、Charlene V. Singh、Tracey R. Friss、John C. MacDonald、Shawn C. Burdette

  DOI：10.1039/c2dt30135k

  日期：——

  tridentate ZinCast-1 utilizes a bis-pyridin-2-ylmethyl-aniline ligand that forms a 5,5-chelate ring upon metal binding. The related photocages ZinCast-2 with a N-[2-(pyridine-2-yl)ethyl]-N-(pyridine-2-ylmethyl)aniline (5,6-chelate ring) and ZinCast-3 with a N,N-bis[2-(pyridine-2-yl)ethyl]aniline (6,6-chelate ring) were synthesized for comparative studies. The complexes formed by the ions Cu2+, Zn2+ and

  已经制备并表征了两代用于Zn 2+的基于硝基苯甲酚的光笼。第一个系列包括三齿ZinCast-1，利用双吡啶-2-基甲基苯胺配体，该配体在与金属结合时形成5，5-螯合物环。具有N- [2-（吡啶-2-基）乙基] -N-（吡啶-2-基甲基）苯胺（5,6-螯合物环）的相关光笼ZinCast-2和具有N，N的ZinCast-3合成了双[2-（吡啶-2-基）乙基]苯胺（6,6-螯合物环）用于比较研究。由离子Cu 2 +，Zn 2+和Cd 2+形成的络合物用UV-Vis光谱法分析了三种ZinCast及其光产物（ZinUnc）的混合物。研究表明，ZinCast-1形成具有最高稳定性的复合物，而ZinCast-3在解笼时在金属亲和力方面表现出最显着的变化。这些结果表明，必须考虑氮原子供体能力的变化以及初始配合物的稳定性，以设计具有所需性质的光笼。合成的结果用于设计ZinCast-4和ZinCast-5，这
• ZinCast-1: a photochemically active chelator for Zn2+
  作者：Celina Gwizdala、Daniel P. Kennedy、Shawn C. Burdette

  DOI：10.1039/b913605c

  日期：——

  Two strategies were applied to the synthesis of ZinCast-1, a nitrobenzhydrol-based caged complex that upon photolysis exhibits a nearly 400-fold difference in binding for Zn2+.

  我们采用两种策略合成了 ZinCast-1，这是一种基于硝基苯甲醇的笼状复合物，光解时与 Zn2+ 的结合力相差近 400 倍。
• Studies of the Optical and Sensing Properties of 1,3,5-Triazine-Cored Star-Shaped (D-π)₃-A Molecules with Various Amino-Donor-Type Cation Receptors
  作者：Hiroki Muraoka、Hikaru Sasaki、Satoshi Ogawa

  DOI：10.1246/bcsj.20180355

  日期：2019.4.15

  We newly designed and synthesized two kinds of 1,3,5-triazine-cored star-shaped (D-π)3-A molecules with 1-aza 15-crown 5-ether receptors (TSM-ACE) and dipicolylamino receptors (TSM-DPA), which possess an intramolecular charge transfer (ICT) nature and exhibit ICT-based optical properties (ICT transition absorption and fluorescence from a ICT excited state). Both TSM-ACE and TSM-DPA display proton-induced optical spectral blue-shifts followed by red-shifts depending on their inherent two-step protonation behavior. Furthermore, TSM-ACE displays optical spectral blue-shifts followed by red-shifts upon stepwise complexation of Mg2+, whereas TSM-DPA displays optical spectral blue-shifts upon the complexation of Zn2+. The cation sensing mechanism can be explained as follows: (i) the initial blue shift is caused by the decreased ICT donor abilities of three amino-donor-type receptors (a decrease of the ICT efficiency) upon binding cations, and (ii) the second red shift is caused by an increased acceptor ability of the 1,3,5-triazine core upon binding cations. Consequently, we revealed that TSM-ACE and TSM-DPA with different cation-recognition functionalities serve as a unique optical sensor capable of visual and distinct detection of not only protons but also different kinds of metal ions.

  我们新设计并合成了两种具有1-氮杂15冠5-醚受体（TSM-ACE）和二吡啶氨基受体（TSM）的1,3,5-三嗪核星形（D-π）3-A分子-DPA），具有分子内电荷转移（ICT）性质，并表现出基于 ICT 的光学特性（ICT 跃迁吸收和来自 ICT 激发态的荧光）。 TSM-ACE 和 TSM-DPA 均显示质子引起的光谱蓝移，然后根据其固有的两步质子化行为发生红移。此外，TSM-ACE 在逐步络合 Mg2+ 时显示光谱蓝移，然后显示红移，而 TSM-DPA 在络合 Zn2+ 时显示光谱蓝移。阳离子传感机制可以解释如下：（i）初始蓝移是由三种氨基供体型受体结合阳离子时ICT供体能力降低（ICT效率降低）引起的，以及（ii）第二个红移是由 1,3,5-三嗪核心结合阳离子时受体能力增强引起的。因此，我们发现具有不同阳离子识别功能的 TSM-ACE 和 TSM-DPA 作为独特的光学传感器，不仅能够视觉和清晰地检测质子，还能够检测不同种类的金属离子。