2-(4-乙氧基羰基喹啉-2-基)喹啉-4-羧酸乙酯 | 912-84-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 中文名称: 2-(4-乙氧基羰基喹啉-2-基)喹啉-4-羧酸乙酯
• 英文名称: 4,4'-diethylester-2,2'-biquinoline
• 英文别名: diethyl 4,4′-dicarboxy-2,2′-biquinoline；Diethyl 2,2'-bicinchoninat；2,2'-Bis-cinchoninsaeure-diethylester；4,4'-bis(ethoxycarbonyl)-2,2-biquinoline；[2,2']biquinolinyl-4,4'-dicarboxylic acid diethyl ester；2,2'-biquinoline-4,4'-dicarboxylic acid diethyl ester；[2,2']biquinolyl-4,4'-dicarboxylic acid diethyl ester；diethyl 2,2-biquinoline-4,4'-dicarboxylic acid；debq；[2,2']Bichinolyl-4,4'-dicarbonsaeure-diaethylester；Ethyl 2-(4-ethoxycarbonylquinolin-2-yl)quinoline-4-carboxylate
• CAS: 912-84-5
• 化学式: C₂₄H₂₀N₂O₄
• 分子量: 400.434
• InChiKey: MHTKEFREHDUDMW-UHFFFAOYSA-N

物化性质

• 熔点：
  160-161 °C
• 沸点：
  586.2±50.0 °C(Predicted)
• 密度：
  1.258±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  30
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  78.4
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  五羰基溴铼(I) 、 2-(4-乙氧基羰基喹啉-2-基)喹啉-4-羧酸乙酯 以 甲苯 为溶剂， 生成 fac-[(diethyl-2,2'-biquinoline-4,4'-dicarboxylate)tricarbonylbromorhenium(I)]
  参考文献：
  名称：

  Towards near-IR emissive rhenium tricarbonyl complexes: Synthesis and characterisation of unusual 2,2′-biquinoline complexes

  摘要：

  Diethyl-2,2'-biquinoline-4,4'-dicarboxylate (debq) reacts with pentacarbonylbromorhenium in toluene to give fac-[Re(CO)(3)(debq)Br]; subsequent reaction with AgOTf in MeCN affords the cationic complex fac-[Re (CO)(3)(debq)(MeCN)]OTf. X-ray crystallographic data on fac-[Re(CO)(3)(debq)Br] show that the debq ligand is coordinated in a bidentate fashion at an angle of 32 degrees from the equatorial plane of the complex: DFT calculations confirm this as the lowest energy conformation.fac-[Re(CO)(3)(debq)Br] and fac-[Re(CO)(3)(debq) (MeCN)]OTf both possess (MLCT)-M-1 absorptions in the visible region, the former most red-shifted to ca. 465 nm. Both complexes demonstrated unusual luminescent properties: in solution, emission appears to be dominated by ligand-centred processes, whereas only (MLCT)-M-3 emission, tailing into the near-IR, was observed in the solid state at 671 (tau = 59 ns) and 711 nm (tau = 19 ns) for fac-[Re(CO)(3)(debq)(MeCN)]OTf and fac-[Re (CO)(3)(debq)Br], respectively. However, the debq ligand is not labile in these complexes, which are robust to competing ligands and coordinating solvents. (C) 2011 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.inoche.2011.06.021
• 作为产物：
  描述：

  2,2'-二辛可宁酸 在 氯化亚砜 作用下， 生成 2-(4-乙氧基羰基喹啉-2-基)喹啉-4-羧酸乙酯
  参考文献：
  名称：

  α-(2-Piperidyl)-2-aryl-4-quinolinemethanols¹

  摘要：

  DOI：

  10.1021/ja01216a087

文献信息

• Adduct Formation of Dichloridodioxidomolybdenum(VI) and Methyltrioxidorhenium(VII) with a Series of Bidentate Nitrogen Donor Ligands
  作者：Ahmad M. Al‐Ajlouni、Alev Günyar、Ming‐Dong Zhou、Paul N. W. Baxter、Fritz E. Kühn

  DOI：10.1002/ejic.200801103

  日期：2009.3

  do not form adducts with MTO, and only 6,6'-dimethyl- and 6,6'-diphenyl-2,2'-bipyridines form adducts with MoO(2)Cl(2). However, these adducts are much less stable than other methyl derivatives of 2,2'-bipridine adducts. The steric strain between the two methyl groups in 3,3-dimethyl-2,2'-bipyridine influences the bipyridine planarity upon complexation and reduces the adduct stability. The thermodynamic

  MoO(2)Cl(2) 和 (CH(3))ReO(3) (MTO) 的各种双齿 N 碱加合物的稳定性在 thf 和 CH(2)Cl(2) 作为溶剂进行了调查。形成常数由基于 1:1 加合物形成的分光光度数据确定。[MoO2Cl(2)L(2)]（L(2) = 二齿氮配体）的加合物形成常数比 [(CH(3))ReO(3) 高 10(4)-10(6) 倍)L(2)] 在相同条件下具有相同的配体。两个系统的加合物稳定性对配体的电子性质非常敏感，并随着它们的供体能力而增加。形成常数与西格玛的哈米特相关性给出了相对较大的反应常数负值（rho(Re) = -5.9，rho(Mo) = -6.6）。稳定性还受空间和应变因素的影响。因此，空间位阻的 6,6'-二取代-2，2'-联吡啶不与 MTO 形成加合物，只有 6,6'-二甲基-和 6,6'-二苯基-2,2'-联吡啶与 MoO(2)Cl(2) 形成加合物。然而，这些加合物的稳定性远低于
• Bidentate Lewis base adducts of molybdenum(VI): Ligand impact on catalytic performance and stability
  作者：Alev Günyar、Fritz E. Kühn

  DOI：10.1016/j.molcata.2009.12.007

  日期：2010.3.17

  t-butyl hydroperoxide as oxidizing agent is strongly influenced by the nature of the ligand L and its steric demand. The complexes, with the sole exception of compound 9 [MoO2Cl2(1,10-phenanthroline-5,6-dione)], are very active and highly selective epoxidation catalysts. The influence of the terminal oxo ligands together with the Lewis base ligands on the Mo center obviously keeps the compounds on a

  溶剂取代的[MoO 2 Cl 2 ]（THF）2与1当量的配合物的反应。二齿氮供体配体产生[MoO 2 Cl 2 L 2 ]类型的络合物（L 2  = 4,5-二氮杂芴-9-一； 1,10-菲咯啉-5,6-二酮； 2,2'-在室温下在惰性条件下以定量收率得到双喹啉4,4'-二羧酸二乙酯，3,6'-双-2-吡啶基-哒嗪; 4,4'-二乙氧基羰基-2,2'-联吡啶）几分钟内达到气体气氛。[MoO 2 Cl 2 L 2的催化活性用叔丁基氢过氧化物作为氧化剂的烯烃环氧化中的[α]配合物受到配体L的性质及其空间需求的强烈影响。除了化合物9 [MoO 2 Cl 2（1,10-菲咯啉-5,6-二酮）]以外，该配合物是非常活泼和高度选择性的环氧化催化剂。末端氧代配体与路易斯碱配体一起对Mo中心的影响显然使化合物保持在相当稳定的电子密度水平上。
• Syntheses, crystal structures and magnetic properties of two halogen bridged dinuclear copper(II) complexes [(4,4′-diethylester-2,2′-biquinoline)2Cu2(μ-X)2X2] (X−=Cl−, Br−)
  作者：Hao Yang、Xiao-Mei Sun、Xiao-Ming Ren

  DOI：10.1016/j.poly.2014.03.043

  日期：2014.11

  Two dinuclear Cu2+ complexes, [(deebq)(2)Cu-2(mu-X)(2)X-2] (deebq = 4,4'-diethylester-2,2'-biquinoline, X- = Cl- for 1 and Br- for 2), were prepared and structurally characterized. The isostructural 1 and 2 crystallize in monoclinic space group P2(1)/c, with quite similar unit cell parameters and packing structures. Two Cu2+ ions related to each other via an inversion center are connected by two halogen anions in a mu(2)-bridge mode, and each Cu2+ ion is coordinated by two N atoms form one deebq ligand and three X- anions to form distorted trigonal bipyramidal coordination geometry in dinuclear Cu2+ complex. The neighboring dinuclear units are held together through intermolecular van der Waals forces. Two complexes show antiferromagnetic (AFM) coupling nature with J/k(B) = -73.4 K for 1 and -83.7 K for 2 within the dinuclear unit. The theoretical analyses utilizing broken-symmetry approach disclosed that the AFM coupling is achieved via orbital overlap in the dinuclear unit for two complexes. (C) 2014 Elsevier Ltd. All rights reserved.
• Toward Exceeding the Shockley−Queisser Limit:  Photoinduced Interfacial Charge Transfer Processes that Store Energy in Excess of the Equilibrated Excited State
  作者：Paul G. Hoertz、Aaron Staniszewski、Andras Marton、Gerard T. Higgins、Christopher D. Incarvito、Arnold L. Rheingold、Gerald J. Meyer

  DOI：10.1021/ja060470e

  日期：2006.6.1

  Nanocrystalline (anatase), mesoporous TiO2 thin films were functionalized with [Ru(bpy)(2)(deebq)](PF6)(2), [Ru(bq)(2)(deeb)](PF6)(2), [Ru(deebq)(2)(bpy)](PF6)(2), [Ru(bpy)(deebq)(NCS)(2)], or [Os(bpy)(2)(deebq)](PF6)(2), where bpy is 2,2'-bipyridine, bq is 2,2'-biquinoline, and deeb and deebq are 4,4'-diethylester derivatives. These compounds bind to the nanocrystalline TiO2 films in their carboxylate forms with limiting surface coverages of 8 (+/- 2) x 10(-8) mol/cm(2). Electrochemical measurements show that the first reduction of these compounds (-0.70 V vs SCE) occurs prior to TiO2 reduction. Steady state illumination in the presence of the sacrificial electron donor triethylamine leads to the appearance of the reduced sensitizer. The thermally equilibrated metal-to-ligand charge-transfer excited state and the reduced form of these compounds do not inject electrons into TiO2. Nanosecond transient absorption measurements demonstrate the formation of an extremely long-lived charge separated state based on equal concentrations of the reduced and oxidized compounds. The results are consistent with a mechanism of ultrafast excited-state injection into TiO2 followed by interfacial electron transfer to a ground-state compound. The quantum yield for this process was found to increase with excitation energy, a behavior attributed to stronger overlap between the excited sensitizer and the semiconductor acceptor states. For example, the quantum yields for [Os(bpy)(2)(dcbq)]/TiO2 were phi(417 nm) = 0.18 +/- 0.02, phi(532.5 nm) = 0.08 +/- 0.02, and phi(683 nm) = 0.05 +/- 0.01. Electron transfer to yield ground-state products occurs by lateral intermolecular charge transfer. The driving force for charge recombination was in excess of that stored in the photoluminescent excited state. Chronoabsorption measurements indicate that ligand-based intermolecular electron transfer was an order of magnitude faster than metal-centered intermolecular hole transfer. Charge recombination was quantified with the Kohlrausch-Williams-Watts model.
• Crystal structures and properties of two Cu(I) complexes based on Keggin-type clusters and diethyl 4,4′-dicarboxy-2,2′-biquinoline acid
  作者：Jiajia Lai、Xianying Duan、Hui Yang、Meilin Wei

  DOI：10.1080/00958972.2018.1460663

  日期：2018.5.19

  Two proton-conductive Cu(I) complexes based on Keggin-type clusters, [Cu(debqdc)(2)](2)[HPW12O40]4H(2)O (1), and [Cu(debqdc)(2)](2)[HPW12O40]debqdc4H(2)O (2), where debqdc is diethyl 4,4-dicarboxy-2,2-biquinoline, were simply synthesized at room temperature. The products were structurally characterized by elemental analyses, infrared spectroscopy, and single-crystal X-ray diffraction analyses. Single-crystal X-ray diffraction analyses revealed that both complexes crystallized in the triclinic space group P-1 and presented two three-dimensional supramolecular networks with one-dimensional hydrophilic channels via hydrogen-bonding interactions and - stacking interactions between the aromatic rings. In the [Cu(debqdc)(2)](+) ion, debqdc acts as a bidentate nitrogen donor ligand in the chelating fashion. The bulky debqdc ligand constrains the Cu(I) metal center within such a rigid environment in a tetrahedral geometry. The two complexes exhibit good proton conductivities (10(-5) 10(-4) S cm(-1)) at 100 degrees C in the relative humidity range 35 98%. The luminescence behaviors of these complexes in the solid state at room temperature have also been investigated. Upon excitation at 285nm, both 1 and 2 display three main emission peaks centered at 470, 520, and 568nm, respectively.