10-methoxybenzo[h]quinoline | 83491-11-6

• 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: 10-methoxybenzo[h]quinoline
• CAS: 83491-11-6
• 化学式: C₁₄H₁₁NO
• 分子量: 209.247
• InChiKey: HYNXSESPAPLRTB-UHFFFAOYSA-N

物化性质

• 沸点：
  387.7±15.0 °C(Predicted)
• 密度：
  1.196±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 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：

  10-methoxybenzo[h]quinoline 在 碘 、 溶剂黄146 作用下， 以 甲醇 、 氯仿 为溶剂， 生成 7,9-diiodo-10-methoxybenzo[h]quinoline
  参考文献：
  名称：

  Proton-Transfer Tautomerism in 10-Hydroxybenzo[h]quinolines:  Heavy Atom Effects and Non-Hydrogen-Bonded Photorotamer Formation in 77 K Glassy Matrixes

  摘要：

  The low-lying triplet states of 10-hydroxybenzo[h]quinoline (HBQ) and its halogenated derivaties 7,9-diiodo-10-hydroxybenzo[h]- quinoline (DIHBQ) in an excited-state intramolecular proton-transfer (ESIPT) process have been investigated. For DIHBQ, which is enhanced by the intramolecular heavy atom effect, the proton-transfer tautomer (i.e., the keto form) phosphorescence that is maximized at 735 nm (tau(p) = 1.75 mus) was resolved in a 77 K methylcyclohexane (MCH) glass. Further transient absorption and 10, sensitization experiments allow us to deduce the population yield and radiative decay rate of the keto triplet state to be 0.85 and 8.8 s(-1), respectively. Upon increasing the excitation intensity, photolysis reactions were observed for both HBQ and DIHBQ in the MCH glass. The reversibility of the photolysis reaction throughout a thawing and freezing cycle led us to conclude that the rupture of an intramolecular hydrogen bond through the excessive energy dissipated does occur. The product exhibits a non-hydrogen-bonding type of enol emission that would otherwise be inaccessible in the hydrogen-bonded enol form because of the ultrafast ESIPT. Accordingly, relative energy levels in different spin manifolds are established during a proton-transfer cycle. The keto-enol reverse proton transfer in the lowest triplet manifold was estimated to be endergonic by similar to7.42 kcal/mol.

  DOI：

  10.1021/jp020288+
• 作为产物：
  描述：

  7,8-苯并喹啉 在 碘苯二乙酸 、 [((1,3-bis(2,6-diisopropylphenyl)-imidazol-2-ylidene)∙CS2)Pd(triphenylphosphine)2](hexafluorophosphate) 作用下， 以 甲醇 为溶剂， 反应 22.0h， 以96%的产率得到10-methoxybenzo[h]quinoline
  参考文献：
  名称：

  咪唑-2-（2-硫代羧酸盐）钯配合物的合成和催化应用† ‡

  摘要：

  钯（II）二聚体[Pd（C，N -C 6 H 4 CH 2 NMe 2）Cl] 2与两当量的NHC·CS 2两性离子配体[NHC = IPr（1,3-二异丙基咪唑-2 -亚烷基），ICy（1,3-二环己基咪唑-2-亚基），IMes（1,3-双（2,4,6-三甲基苯基）亚咪唑-2-亚基），IDip（1,3-双（2，在NH 4 PF 6存在的情况下，将SIMes（1,3-双（2,4,6-三甲基苯基）咪唑啉-2-亚甲基）（6-二异丙基苯基）咪唑-2-亚基）生成阳离子产物[Pd （C，N -C 6 H 4 CH2 NMe 2）（S 2 C·NHC）] +。以类似的方式，从相应的二聚体[Pd]获得化合物[Pd（ C， N -bzq）（S 2 C·NHC）] +（bzq =苯并[ h ]喹啉基，NHC = ICy，IMes，IDip）。 （ C， N- bzq）Cl] 2。用NHC处理[PdCl 2（PPh

  DOI：

  10.1039/c2dt31413d

文献信息

• Selective Determination of Beryllium(II) Ion at Picomole per Decimeter Cubed Levels by Kinetic Differentiation Mode Reversed-Phase High-Performance Liquid Chromatography with Fluorometric Detection Using 2-(2‘-Hydroxyphenyl)-10-hydroxybenzo[<i>h</i>]quinoline as Precolumn Chelating Reagent
  作者：Hiroaki Matsumiya、Hitoshi Hoshino

  DOI：10.1021/ac0260847

  日期：2003.2.1

  A highly sensitive and selective method for the determination of the Be(II) ion has been developed by the use of reversed-phase high-performance liquid chromatography (HPLC) with fluorometric detection using 2-(2‘-hydroxyphenyl)-10-hydroxybenzo[h]quinoline (HPHBQ) as a precolumn (off-line) chelating reagent. The reagent HPHBQ has been designed to form the kinetically inert Be chelate compatible with high fluorescence yield, which is appropriate to the HPLC-fluorometric detection system. The Be−HPHBQ chelate is efficiently separated on a LiChrospher 100 RP-18(e) column with a methanol (58.3 wt %)−water eluent containing 20 mmol kg-1 of tartaric acid and is fluorometrically detected at 520 nm with the excitation at 420 nm. Under the conditions used, the concentration range of 20−8000 pmol dm-3 of Be(II) ion can be determined without interferences from 10 μmol dm-3 each of common metal ions, typically Al(III), Cu(II), Fe(III), and Zn(II), and still more coexistence of Ca(II) and Mg(II) ions at 0.50 mmol dm-3 and 5.0 mmol dm-3, respectively, is tolerated. The detection limit (3σ baseline fluctuation) is 4.3 pmol dm-3 (39 fg cm-3). The extraordinarily high sensitivity with toughness toward the matrix influence was demonstrated with the successful application to environmental Be analyses, such as determination of Be in rainwater and tap water.

  利用反相高效液相色谱（HPLC）结合荧光检测法，采用2-(2'-羟基苯基)-10-羟基苯并[h]喹啉（HPHBQ）作为前柱（离线）螯合剂，开发了一种高灵敏度和选择性的Be(II)离子测定方法。设计了HPHBQ试剂，使其能形成动力学上不活泼的Be螯合物，并且具有高荧光产率，适合于HPLC-荧光检测系统。在含有20 mmol kg-1 酒石酸的甲醇（58.3 wt %）-水溶液中，Be−HPHBQ螯合物在LiChrospher 100 RP-18(e)柱上被高效分离，并在420 nm激发下于520 nm处进行荧光检测。在所用条件下，Be(II)离子的浓度范围为20−8000 pmol dm-3，不受常见金属离子（如Al(III)、Cu(II)、Fe(III)和Zn(II)，各10 μmol dm-3）以及Ca(II)和Mg(II)离子分别共存于0.50 mmol dm-3和5.0 mmol dm-3的影响。检测限（3σ基线波动）为4.3 pmol dm-3（39 fg cm-3）。该方法极佳的灵敏度和对基质影响的强韧性通过对环境样品中Be的分析得到了验证，例如对雨水和自来水中的Be进行测定。
• Photophysics of 10-Hydroxybenzo[<i>h</i>]quinoline in Aqueous Solution
  作者：Pi-Tai Chou、Ching-Yen Wei

  DOI：10.1021/jp961368e

  日期：1996.1.1

  determine the fluorescence species and dynamics of excited-state proton transfer (ESPT) of 10-hydroxybenzo[h]quinoline (HBQ) in water. The acidity of the hydroxyl proton and protonated benzoquinolinic nitrogen for various BQ derivatives in both ground and excited states has been measured by pH-dependent absorption and emission spectroscopies. The results, in combination with fluorescence decay dynamics

  为了确定10-羟基苯并[ h]的激发态质子转移（ESPT）的荧光种类和动力学，已经合成并研究了各种7,8-苯并喹啉（BQ）衍生物。水中的]喹啉（HBQ）。对于各种BQ衍生物，无论是处于基态还是处于激发态，其羟基质子和质子化的苯并喹啉氮的酸度均已通过pH依赖的吸收光谱和发射光谱法进行了测量。结果与荧光衰减动力学相结合，得出结论：对于HBQ，无论是中性，质子化还是去质子化形式，在激发态下酮-互变异构体的形成都是强力的，并且在宽广的pH范围内占主导地位。 。该过程仅受到与自由水分子相关的质子给予或接受速率的动态限制。结果还表明，羟基氧和苯并喹啉氮之间的激发态共振电荷转移充当了ESPT反应的驱动力。
• Directing Group‐Promoted Inert C−O Bond Activation Using Versatile Boronic Acid as a Coupling Agent
  作者：Ram Ambre、Ting‐Hsuan Wang、Anmei Xian、Yu‐Shiuan Chen、Yu‐Fu Liang、Titel Jurca、Lili Zhao、Tiow‐Gan Ong

  DOI：10.1002/chem.202004132

  日期：2020.12.18

  strategy facilitates the efficient catalytic cross‐coupling of methoxyarenes with a variety of organoboron reagents. Directing groups facilitate the activation of inert C−O bonds in under‐utilized aryl methyl ethers enabling their adaptation for C−C cross‐coupling reactions as less toxic surrogates to the ubiquitous haloarenes. The method reported enables C−C cross‐coupling with readily available and economical

  一个简单的Ni（cod）2卡宾介导的策略促进了甲氧基芳烃与多种有机硼试剂的高效催化交叉偶联。定向基团可促进未充分利用的芳基甲基醚中惰性C-O键的活化，使它们能够适应C-C交叉偶联反应，因为对普遍存在的卤代芳烃的毒性较小。报道的方法可以使C-C与现成的经济型芳基硼酸试剂进行交叉偶联，这是前所未有的，并且可以与具有类似高反应活性的其他有机硼试剂进行比较。据报道，扩展了引导基团辅助的化学选择性的C-O键裂解，并进一步应用于合成新型双官能联芳基。
• Spatially isolated palladium in porous organic polymers by direct knitting for versatile organic transformations
  作者：Xinbo Wang、Shixiong Min、Swapan K. Das、Wei Fan、Kuo-Wei Huang、Zhiping Lai

  DOI：10.1016/j.jcat.2017.08.030

  日期：2017.11

  Electro-beam induced Pd atom crystallization was observed for the first time in organic polymer and revealed the ultrafine dispersion of palladium atoms. Challenging types of Suzuki-Miyaura couplings, reductive coupling of aryl halides and oxidative coupling of arylboronic acid were successively catalyzed by PPPd in aqueous media. Also catalytically selective CH functionalization reactions were achieved

  我们在这里报告一种直接编织的方法，用于从广泛使用的Pd（PPh 3）4制备高度坚固，有效，同时耐空气和湿气以及易于回收的三维（3D）多孔聚合物-Pd网络（PPPd）。首次在有机聚合物中观察到电子束诱导的Pd原子结晶，并揭示了钯原子的超细分散。在水性介质中，PPPd依次催化了具有挑战性的Suzuki-Miyaura偶联类型，芳基卤化物的还原偶联和芳基硼酸的氧化偶联。也是催化选择性碳H官能化反应比常规的Pd均相催化剂效率高出几个数量级。本文开发的策略为易于制造但高效的多相催化提供了一种实用的方法。
• A Highly Selective Catalytic Method for the Oxidative Functionalization of C−H Bonds
  作者：Allison R. Dick、Kami L. Hull、Melanie S. Sanford

  DOI：10.1021/ja031543m

  日期：2004.3.3

  This communication describes a new and highly practical Pd(II)-catalyzed method for the regio- and chemoselective oxidative functionalization of arenes and alkanes. Carbon-hydrogen bonds of substrates that contain a variety of directing groups (e.g., pyridine, azobenzene, pyrazole, and imine derivatives) are selectively transformed into esters, ethers, and aryl-halides under mild conditions. The scope

  该通讯描述了一种新的、高度实用的 Pd(II) 催化方法，用于芳烃和烷烃的区域和化学选择性氧化功能化。含有多种导向基团（例如，吡啶、偶氮苯、吡唑和亚胺衍生物）的底物的碳氢键在温和条件下选择性地转化为酯、醚和芳基卤化物。描述了该反应在底物、导向基团和氧化剂方面的范围，并提出了初步的催化循环。