2-(bromomethyl)-5-chloro-8-methoxyquinoline | 172033-46-4

• 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-(bromomethyl)-5-chloro-8-methoxyquinoline
• 英文别名: 5-Chloro-8-methoxy-2-(bromomethyl)quinoline；2-bromomethyl-5-chloro-8-methoxyquinoline
• CAS: 172033-46-4
• 化学式: C₁₁H₉BrClNO
• 分子量: 286.556
• InChiKey: ZUUIVRAEWWPJBF-UHFFFAOYSA-N

物化性质

• 熔点：
  151-153 °C(Solv: ethyl acetate (141-78-6); hexane (110-54-3))
• 沸点：
  373.2±37.0 °C(Predicted)
• 密度：
  1.572±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  22.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-(bromomethyl)-5-chloro-8-methoxyquinoline 在 lithium chloride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 5-Chloro-2-[[16-[(5-chloro-8-hydroxyquinolin-2-yl)methyl]-1,4,10,13-tetraoxa-7,16-diazacyclooctadec-7-yl]methyl]quinolin-8-ol
  参考文献：
  名称：

  一种新的 K+ 和 Ba2+ 高选择性大环：通过络合形成伪第二大环的影响

  摘要：

  一种能够在络合时形成伪第二大环的新大环化合物已被表征。5-氯-8-羟基喹啉 (CHQ)-取代的 diaza-18-crown-6 (1) 化合物具有独特的络合特性。在甲醇中与 1 形成 K{sup +} 和 Ba{sup 2+} 复合物的 log K 值大于与所有其他套索醚形成的 K{sup +} 和 Ba{sup 2+} 复合物的 log K 值。1-Ba{sup 2+} 复合体的 log K 值与密码体 [2.2. 2]-Ba{sup 2+} 复合体。Ba{sup 2+} 对其他碱土阳离子和 K{sup +} 对 Na{sup +} 在甲醇中的选择性因子分别为 >10{sup 7} 和接近 10{sup 3}，它们是有史以来报告的套索醚的最高系数。而且，Ba{sup 2+} 对其他碱土阳离子的选择性 1 大于迄今为止研究的任何其他穴状物质。UV-可见光、{sup 1}H NMR 光谱和

  DOI：

  10.1021/ja00151a014

文献信息

• Quinoline-Containing Calixarene Fluoroionophores: A Combined NMR, Photophysical and Modeling Study
  作者：Alessandro Casnati、Francesco Sansone、Andrea Sartori、Luca Prodi、Marco Montalti、Nelsi Zaccheroni、Franco Ugozzoli、Rocco Ungaro

  DOI：10.1002/ejoc.200390206

  日期：2003.4

  alkaline earth metal ions. Combined NMR, photophysical, and modeling studies disclosed the peculiar conformational and coordination features of monovalent and divalent metal ion complexes. Lanthanide metal ion complexes were prepared and studied in acetonitrile solution showing good luminescence in the case of Nd3+, Yb3+, and Er3+ ions. (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003)

  8-烷氧基-5-氯喹啉荧光团附加在具有两种不同方向的杯[4]芳烃三酰胺的下边缘。在配体 1 中，喹啉部分通过吡啶 C2 原子连接到杯芳烃骨架，而在配体 2 中，它通过生色团的酚氧原子连接。在氯仿和甲醇溶液中研究的两种配体的结合特性表明它们是有效的氟离子载体，在碱金属和碱土金属离子中对钠离子和锶离子具有选择性。结合核磁共振、光物理和建模研究揭示了单价和二价金属离子配合物的独特构象和配位特征。在乙腈溶液中制备和研究镧系金属离子配合物，在 Nd3+、Yb3+ 和 Er3+ 离子的情况下显示出良好的发光。
• Synthesis of New Pyridinoazacrown Ethers Containing Aromatic and Heteroaromatic Proton Ionizable Substituents
  作者：Andrei V. Bordunov、Paul C. Hellier、Jerald S. Bradshaw、N. Kent Dalley、Xiaolan Kou、Xian Xin Zhang、Reed M. Izatt

  DOI：10.1021/jo00124a022

  日期：1995.9

  Methods for the synthesis of pyridinocrowns functionalized with various proton ionizable groups have been elaborated. Sixteen new ligands containing pyridine rings as part of the macrocycle or as a side arm have been prepared. Different interactive abilities of the OH and NH functions of 3,9-dioxa-6-azaundecane-1,11-diol (3) in strong base allowed the synthesis of pyridinoazacrowns 1 and 2 by cyclization with 2,6-bis((tosyloxy)methyl)pyridine (4) and THP-protected 4-hydroxy-2,6-bis(tosyloxy)methyl)pyridine (5). Pyridinoazacrown 1 was functionalized with different proton ionizable side arms by treatment first with formaldehyde in methanol to form the N-methoxymethyl derivative 6 and then treating 6 with 5-chloro-8-hydroxyquinoline or the appropriate substituted phenol. Pyridinoaza-18-crown-6 ligands containing p-methylphenol (7), p-methoxyphenol (8), p-chlorophenol (9),p-fluorophenol (10),p-cyanophenol (11), 2-formyl-4-bromophenol (12), or 5-chloro-8-hydroxyquinoline (13) groups were prepared by this process. Pyridinoazacrowns 1 and 2 were alkylated with 2-hydroxy-5-nitrobenzyl chloride or 5-chloro-8-methoxy-2-(bromomethyl)quinol followed by removal of the protecting groups to form p-nitrophenol- and 5-chloro-8-hydroxy-2-quinolinyl-substituted ligands (16, 18, and 21). Macrocycles 22 and 23 containing proton ionizable triazole and phenol functions inside the macrocyclic cavity and a pyridine side arm were prepared by cyclization of the appropriate dihalide with 6-(2'-pyridylmethyl)-3,9-dioxa-6-azaundecane-1,11-diol followed by cleavage of the THP or methoxy protecting groups. Preliminary complexation data show that the phenol-substituted pyridinoaza-18-crown-6 ligands form strong complexes with various metal cations and exhibit high selectivity toward Ag+. Macrocycle 16 containing a p-nitrophenol substituent formed a complex with benzylamine. The crystal structures for 16 and its benzylamine complex are also given here.
• Origins of ‘on–off’ fluorescent behavior of 8-hydroxyquinoline containing chemosensors
  作者：R. Todd Bronson、Marco Montalti、Luca Prodi、Nelsi Zaccheroni、Randy D. Lamb、N. Kent Dalley、Reed M. Izatt、Jerald S. Bradshaw、Paul B. Savage

  DOI：10.1016/j.tet.2004.08.062

  日期：2004.11

  Derivatives of 8-hydroxyquinoline were used as model compounds to probe the pathways of non-radiative relaxation of fluorophores in two fluorescent chemosensors. Results suggest that both photo-induced proton transfer and photo-induced electron transfer contribute to quenching the fluorescence of the chemosensors. Crystal structures of an 8-hydroxyquinoline-containing chemosensor complexed to various metal ions indicate that a proton shift occurs concomitant with complex formation. This proton shift precludes both photo-induced proton and electron transfer allowing fluorescence emission from chemosensor-metal ion complexes. (C) 2004 Elsevier Ltd. All rights reserved.
• Efficient Immobilization of a Cadmium Chemosensor in a Thin Film:  Generation of a Cadmium Sensor Prototype
  作者：R. Todd Bronson、David J. Michaelis、Randy D. Lamb、Ghaleb A. Husseini、Paul B. Farnsworth、Matthew R. Linford、Reed M. Izatt、Jerald S. Bradshaw、Paul B. Savage

  DOI：10.1021/ol050027t

  日期：2005.3.1

  The development of an ion-selective chemosensor for Cd2+ allows generation of a "real-time" sensor, Immobilization of the chemosensor on quartz was achieved in a simple monolayer and in a thin film using a polymer intermediary. As intended, the thin film contains much more chemosensor than the monolayer and provides measurable responses to aqueous Cd2+ concentrations below 1 mu M. Alkali and alkaline earth ions do not interfere with Cd2+ sensing; Zn2+ and Cu2+ are potential interferents.
• A New Highly Selective Macrocycle for K+ and Ba2+: Effect of Formation of a Pseudo Second Macroring through Complexation
  作者：Xian Xin Zhang、Andrei V. Bordunov、Jerald S. Bradshaw、N. Kent Dalley、Xiaolan Kou、Reed M. Izatt

  DOI：10.1021/ja00151a014

  日期：1995.11

  of Ksup +} and Basup 2+} complexes with 1 in methanol are larger than those for the Ksup +} and Basup 2+} complexes with all other lariat ethers. The log K value for the 1-Basup 2+} complex is the same magnitude as that of the cryptand [2.2. 2]-Basup 2+} complex. Selectivity factors for Basup 2+} over other alkaline-earth cations and for Ksup +} over Nasup +} in methanol are >10sup 7} and

  一种能够在络合时形成伪第二大环的新大环化合物已被表征。5-氯-8-羟基喹啉 (CHQ)-取代的 diaza-18-crown-6 (1) 化合物具有独特的络合特性。在甲醇中与 1 形成 Ksup +} 和 Basup 2+} 复合物的 log K 值大于与所有其他套索醚形成的 Ksup +} 和 Basup 2+} 复合物的 log K 值。1-Basup 2+} 复合体的 log K 值与密码体 [2.2. 2]-Basup 2+} 复合体。Basup 2+} 对其他碱土阳离子和 Ksup +} 对 Nasup +} 在甲醇中的选择性因子分别为 >10sup 7} 和接近 10sup 3}，它们是有史以来报告的套索醚的最高系数。而且，Basup 2+} 对其他碱土阳离子的选择性 1 大于迄今为止研究的任何其他穴状物质。UV-可见光、sup 1}H NMR 光谱和