6,7-dihydro-2,11-dimethyldipyrido<1,2-a:2',1'-c>pyrazinediium dibromide | 4150-51-0

• 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
• 英文名称: 6,7-dihydro-2,11-dimethyldipyrido<1,2-a:2',1'-c>pyrazinediium dibromide
• 英文别名: 6,7-Dihydro-2,11-dimethyldipyrido<1,2-a:2',1'-c>pyrazinium dibromide；2,11-dimethyl-6,7-dihydrodipyrido<1,2-a:2',1'-c>pyrazinium dibromide；6,7-dihydro-2,11-dimethyldipyrido[1,2-a:2,1-c]pyrazinium dibromide；2,11-dimethyl-6,7-dihydrodipyrido[1,2-a:2',1'-c]pyrazinium dibromide；[Me2EDQ]Br2；MDQ；4,13-Dimethyl-7,10-diazoniatricyclo[8.4.0.02,7]tetradeca-1(10),2(7),3,5,11,13-hexaene;bromide
• CAS: 4150-51-0
• 化学式: 2Br*C₁₄H₁₆N₂
• 分子量: 372.102
• InChiKey: AJXYQVGHSRJLNL-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  -1.44
• 重原子数：
  17
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  7.8
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  6,7-dihydro-2,11-dimethyldipyrido<1,2-a:2',1'-c>pyrazinediium dibromide 在 Sephadex DEAE A-50 resin 作用下， 以 甲醇 为溶剂， 生成 6,7-Dihydro-2,11-dimethyldipyrido<1,2-a:2',1'-c>pyrazinium dichloride
  参考文献：
  名称：

  Free-Energy Dependence of Electron-Transfer Rate Constants at Si/Liquid Interfaces

  摘要：

  Differential capacitance vs potential and current density vs potential measurements have been used to characterize the interfacial energetics and kinetics, respectively, of n-type Si electrodes in contact with a series of one-electron, outer-sphere redox couples. The differential capacitance data yielded values for the electron concentration at the surface of the semiconductor as well as values for the driving force of the interfacial electron-transfer event at Si/CH3OH-viologen(2+/+) junctions. The differential capacitance vs potential measurements were essentially independent of the ac frequency imposed on the interface, with linear Bode plots (log\impedance\vs log frequency, at a fixed potential) between approximate to 10(3) and approximate to 10(5) Hz, with slopes typically between -0.99 and -1.00. The slopes of C-2-E (Mott-Schottky) plots were in excellent agreement with theory, and little frequency dispersion was observed in the x-intercepts of such plots. The conduction band edge of the n-type Si anodes was invariant to within +/-40 mV in response to a variation in the redox potential of the solution of greater than 400 mV, indicating "ideal" interfacial energetic behavior of this system with no evidence for Fermi level pinning.,. From these measurements, the surface-state density of the Si/CH3OH contact can be estimated as <10(11) cm(2), i.e., less than 1 defect for 10(4) surface atoms. The current density vs potential plots exhibited a first-order kinetic dependence on the concentration of electrons at the semiconductor surface and a first-order kinetic dependence on the concentration of accepters in the solution. Rate constants for transfer of charge from the semiconductor to the acceptor were determined as a function of the driving force for the interfacial charge-transfer event. The rate constants varied from 4 x 10(-18) cm(4) s(-1) to 6 x 10(-17) cm(4) s(-1) and were well fit to Marcus-type behavior, with a reorganization energy of 0.7 eV and a maximum rate constant at optimal exoergicity of 6 x 10(-17) cm(4) s(-1). This maximum rate constant value is in excellent agreement with theoretical expectations for transfer of charge from a delocalized carrier in a semiconductor to a one-electron, outer-sphere redox acceptor dissolved in the electrolyte solution.

  DOI：

  10.1021/jp972087p
• 作为产物：
  描述：

  4-甲基吡啶 在 palladium 10% on activated carbon 作用下， 以 硝基苯 为溶剂， 生成 6,7-dihydro-2,11-dimethyldipyrido<1,2-a:2',1'-c>pyrazinediium dibromide
  参考文献：
  名称：

  Ranganayakulu; Murthy, Journal of the Indian Chemical Society, 2010, vol. 87, # 3, p. 309 - 316

  摘要：

  DOI：
• 作为试剂：
  描述：

  (E)-(4-hydroxy-3-methylbut-2-enyl)phosphonophosphoric acid 在 sodium dithionite 、 IspH 、 6,7-dihydro-2,11-dimethyldipyrido<1,2-a:2',1'-c>pyrazinediium dibromide 作用下， 反应 0.5h， 生成 3-甲基丁-2-烯基膦酰磷酸氢酯 、 二磷酸 P-(3-甲基-3-丁烯-1-基)酯
  参考文献：
  名称：

  重新审视磷酸脱氧木酮糖途径中的 IspH 催化系统：实现高活性

  摘要：

  从两个 C(5) 异戊二烯构件、异戊二烯基二磷酸 (IPP) 及其异构体二甲基烯丙基二磷酸 (DMAPP) 中，类异戊二烯家族的 30 000 多个成员在自然界中使用两种生物合成途径构建而成，甲羟戊酸 (MVA) 途径和磷酸脱氧木酮糖 (DXP) 途径。DXP 通路的 IspH 是一种含有铁硫簇的蛋白质，催化 DXP 通路的还原脱水反应。在文献中，广泛的大肠杆菌 IspH 活动已被报道（2.0 nmol min(-1) mg(-1) 到 3.4 micromol min(-1) mg(-1)）。对于如此广泛的活性，反应测定是在许多不同条件下进行的，无法直接比较活性和确定导致 IspH 活性如此巨大差异的关键因素。在这项工作中，我们系统地研究了氧化还原介质在 IspH 催化中的作用，使用大肠杆菌 IspH 作为酶，连二亚硫酸盐作为最终电子源。我们的研究不仅表明了铁硫簇的重要性，而且相对于大肠杆菌

  DOI：

  10.1021/ja903778d

文献信息

• Diquat Derivatives: Highly Active, Two-Dimensional Nonlinear Optical Chromophores with Potential Redox Switchability
  作者：Benjamin J. Coe、John Fielden、Simon P. Foxon、James A. Harris、Madeleine Helliwell、Bruce S. Brunschwig、Inge Asselberghs、Koen Clays、Javier Garín、Jesús Orduna

  DOI：10.1021/ja103289a

  日期：2010.8.4

  optical (NLO) responses with reversible redox chemistry. The chromophores have been characterized as their PF(6)(-) salts by using various techniques including electronic absorption spectroscopy and cyclic voltammetry. Their visible absorption spectra are dominated by intense pi --> pi* intramolecular charge-transfer (ICT) bands, and all show two reversible diquat-based reductions. First hyperpolarizabilities

  在本文中，我们详细研究了双季铵化 2,2'-联吡啶 (diquat) 衍生物的构效关系。已经合成了 16 种新的发色团，在氨基电子供体取代基、π 共轭桥和烷基双季铵化单元中发生了变化。我们的目标是将非常大的二维 (2D) 二次非线性光学 (NLO) 响应与可逆氧化还原化学结合起来。通过使用各种技术，包括电子吸收光谱和循环伏安法，生色团已被表征为它们的 PF(6)(-) 盐。它们的可见吸收光谱以强烈的 pi --> pi* 分子内电荷转移 (ICT) 带为主，并且都显示出两种基于敌草快的可逆还原。通过使用 800 nm 激光的超瑞利散射测量了第一超极化率 beta，ICT 波段的斯塔克光谱提供了估计的静态第一超极化率 beta(0)。直接和间接导出的 beta 值很大，并且随着 pi 共轭程度和电子供体强度的增加而增加。扩展季铵化烷基链接总是会增加 ICT 能量并降低敌草快减少的 E(1/2)
• Bipyridinium and Phenanthrolinium Dications for Metal‐Free Hydrodefluorination: Distinctive Carbon‐Based Reactivity
  作者：Katherine I. Burton、Iris Elser、Alexander E. Waked、Tobias Wagener、Ryan J. Andrews、Frank Glorius、Douglas W. Stephan

  DOI：10.1002/chem.202101534

  日期：2021.8.11

  [2 b]2+) were prepared and evaluated for use in the initiation of hydrodefluorination (HDF) catalysis. Compound [2 a]2+ proved highly effective towards generating catalytically active silylium cations via Lewis acid-mediated hydride abstraction from silane. This enabled the HDF of a range of aryl- and alkyl- substituted sp3(C−F) bonds under mild conditions. The protocol was also adapted to effect the

  报道了衍生自联吡啶鎓和菲咯啉鎓的新型路易斯酸的开发。氢化物离子亲和力 (HIA) 值的计算表明邻位和对位的碳基路易斯酸度较高。这部分源于芳族骨架上的广泛 LUMO 离域。物种 [C 10 H 6 R 2 N 2 CH 2 CH 2 ] 2+ (R=H [1 a] 2+ , Me [1 f] 2+ , t Bu [1 g] 2+ ) 和 [C 12 H 4 R 4N 2 CH 2 CH 2 ] 2+（R=H [2 a] 2+，Me [2 b] 2+）被制备并评估用于引发加氢脱氟（HDF）催化。化合物[2 a] 2+被证明对于通过路易斯酸介导的从硅烷中提取氢化物生成具有催化活性的甲硅烷阳离子非常有效。这使得在温和条件下能够形成一系列芳基和烷基取代的 sp 3 ( CF ) 键的 HDF 。该方案还适用于实现顺式-2,4,6-(CF 3 ) 3 C 6 H 9 的氘代脱氟. 显示出作为氢化物受体，分离中性物质
• Radical cations of some low-potential viologen compounds. Reduction potentials and electron-transfer reactions
  作者：Robert F. Anderson、Kantilal B. Patel

  DOI：10.1039/f19848002693

  日期：——

  The one-electron reduction potentials (E1) of certain pyrazinediium, diazepinediium and diazocinediium viologen compounds substituted with methyl groups, V2+, have been determined from the position of the one-electron transfer equilibria with reference compounds using pulse radiolysis. E1 ranges from –491 ± 6 mV (vs NHE) for 6,7-dihydro-2,11-dimethyldipyrido-[1,2-a : 2′,1′-c]pyrazinediium dibromide

  某些吡嗪二酮，二氮杂二氮杂和重氮电影二茂氮化合物被甲基V 2+取代后的单电子还原电位（E 1）已通过脉冲辐射分解法从参考化合物的单电子转移平衡位置确定。对于1,7,7-二氢-2,11-二甲基二吡啶基-[1,2- a：2'，1'- c ]吡嗪二溴化物（V21 2 +），E 1的范围为–491±6 mV（vs NHE）-对于6,7,8,9-tetrahydro-2,3,12,13-tetramethyldipyrido [1,2- a：2'，1'- c ] [1,4] dizocinediium dibromide （V42 2+）。
• Conformational studies of annulated 2,2'-bipyridinium salts
  作者：Carmen Campa、Jaime Camps、Jose Font、Pedro De March

  DOI：10.1021/jo00380a008

  日期：1987.2
• Kinetics of reduction of eight viologens by dithionite ion
  作者：K. Tsukahara、R. G. Wilkins

  DOI：10.1021/ja00295a013

  日期：1985.5