1,2-双(6-甲基吡啶-2-基)-1,2-乙二酮 | 6630-11-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 1,2-双(6-甲基吡啶-2-基)-1,2-乙二酮
• 英文名称: 1,2-bis(6-methylpyridin-2-yl)ethane-1,2-dione
• 英文别名: 6,6'-dimethyl-2,2'-pyridil；6.6'-Dimethyl-α-pyridil；bis-(6-methyl-pyridin-2-yl)-ethanedione；bis-(6-methyl-[2]pyridyl)-ethanedione；Bis-(6-methyl-[2]pyridyl)-aethandion；bis(6-methyl-2-pyridyl) diketone
• CAS: 6630-11-1
• 化学式: C₁₄H₁₂N₂O₂
• 分子量: 240.261
• InChiKey: GXRQKSBITVLBQD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  59.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1,2-双(6-甲基吡啶-2-基)-1,2-乙二酮 在 lead(II) oxide 作用下， 生成 bis(6-methylpyridin-2-yl)methanone
  参考文献：
  名称：

  Mathes; Sauermilch, Chemische Berichte, 1953, vol. 86, p. 109

  摘要：

  DOI：
• 作为产物：
  描述：

  6,6'-dimethyl-2,2'-pyridoin 在 碘 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以59%的产率得到1,2-双(6-甲基吡啶-2-基)-1,2-乙二酮
  参考文献：
  名称：

  2,2′-Pyridoin derivatives protect HL-60 cells against oxidative stress

  摘要：

  Focusing on 2,2 '-pyridoin (1, 1,2-di(2-pyridyl)-1,2-ethenediol) and its synthetic derivatives as the lead compound of the potent antioxidative enediol, their protective effect against oxidative stress was evaluated on the HL-60 cell system. 2,2 '-Pyridoins showed no remarkable cytotoxic effect on HL-60 cells. The derivatives 1, 2, 3, 5, and 6 inhibited H(2)O(2)-induced cell death and intracellular oxidative stress more significantly than ascorbic acid. Since 2,2 '-pyridoins are oxidized to the diketones, 2,2 '-pyridils, in a protic solvent, the antioxidant activity of 2,2 '-pyridils was also investigated. 2,2 '-Pyridils showed antioxidant activity in the cell; however, the activity was lower than that of 2,2 '-pyridoins. These results suggested that 2,2 '-pyrdoin derivatives can be good cytoprotective agents against oxidative stress. (c) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2008.08.057

文献信息

• Metal-to-ligand charge-transfer excited-states in binuclear copper(I) complexes. Tuning MLCT excited-states through structural modification of bridging ligands. A resonance Raman study
  作者：Mark R. Waterland、Amar Flood、Keith C. Gordon

  DOI：10.1039/a909121a

  日期：——

  The resonance Raman spectra of the ground- and lowest excited-states for a series of binuclear copper(I) complexes with bridging ligands based on 2,3-di-(2-pyridyl)quinoxaline have been measured. Analyses of the ground-state resonance Raman spectra show strong enhancement of an inter-ring stretching mode and quinoxaline-based modes; consistent with the Frank–Condon state having bonding changes about

  共鸣 拉曼光谱桥联的一系列双核铜（I）配合物的基态和最低激发态的分布配体 基于 2,3-二-（2-吡啶基）喹喔啉已被测量。基态共振分析拉曼光谱显着增强了环间拉伸模式和基于喹喔啉的模式；与Frank-Condon态相一致，在铜（I）中心和喹喔啉环系上具有键变化。电子吸收数据还表明，最初形成的MLCT状态定位于喹喔啉环系统。激发态共振拉曼光谱 对配合物显示相似的光谱特征，这些配合物在 吡啶基 桥接环 配体。他们展示光谱 与 自由基阴离子 的桥梁 配体。这与金属到金属的激发态的形成是一致的。配体 自然界中的电荷转移以及 自由基阴离子 位于桥的喹喔啉环系上 配体。
• Synthesis, Characterisation and Crystal Structure of a Co-crystal of Two Components: 1,2-bis(6-methylpyridin-2-yl)ethane-1,2-dione and 1-(pyridin-2-yl)-2-(6-methylpyridin-2-yl)ethane-1,2-dione
  作者：M. Judith Percino、Víctor M. Chapela、Omar Urzúa、Héctor Toribio、Cecilia Rodríguez-Barbarín

  DOI：10.3184/030823407x200434

  日期：2007.3

  A condensation reaction of an equimolar ratio of 2-pyridinecarboxaldehyde and (6-methylpyridin-2-yl)methanol without a catalyst in a solvent-free reaction at 140°C was expected to yield 2-hydroxy-[1,2-bis(6-methylpyridin-2-yl)]ethan-1-one. FT-IR spectroscopy of the yellow-brown solid reaction product indicated the presence of a –CO–COH– group. The solid compound was treated with cyclohexane and green

  2-吡啶甲醛和（6-甲基吡啶-2-基）甲醇等摩尔比的缩合反应在无催化剂的情况下，在140°C下的无溶剂反应中预计会产生2-羟基-[1,2-双（ 6-methylpyridin-2-yl)]ethan-1-one。黄褐色固体反应产物的 FT-IR 光谱表明存在 -CO-COH- 基团。固体化合物用环己烷处理，产生绿色晶体。通过FT-IR、1H NMR、EI质谱和单晶X射线衍射对晶体进行表征。通过单晶 X 射线衍射确定的分子和晶体结构解析出一种晶体，该晶体显示两种分子组分 [C13H10N2O2 和 C14H12N2O2]，比例为 60.4:39.6 [C13.40H10.79N2O2]。两种化合物在三斜空间群 P-1 中共结晶，a = 7.859(5), b = 8.021(14), c = 9.060(5) Å，α = 101.36(2)°, β = 90.06(3)°, γ = 90.92(3)°
• Process to obtain dimers, trimers and up to polymers from pyridinmethanol derivatives compounds
  申请人：PERCINO ZACARIAS Maria Judith

  公开号：US20090043063A1

  公开（公告）日：2009-02-12

  The process of the current invention, named Percino-Chapela, has as one of its main novelty features that starting from pyridinmethanol derivatives, a dimerization or polymerization reaction of pyridinic alcohols is carried out in order to produce novel products, the process of the current invention has the following aspects that characterize it: it is carried out in the absence or presence of some solvent, during the process of the current invention, temperature may be or may be not used as catalyst, in the process of the current invention the reaction may be or may not be catalyzed by the presence of a catalyst (acid or base), the resultant products can be produced and separated in an easy way, in the process of the current invention starting from pyridinic alcohols the resultant ethenediols can be produced by a single step reaction, the pyridinmethanol derivatives used as starting compounds, do not oxidize as easily and their handling is easier than that of other compounds previously used that oxidize easily, the products produced with etheneidol parts can be used as antioxidants due to their capacity to act as free radicals scavengers.

  本发明的过程名为Percino-Chapela，其主要的创新特点之一是从吡啶甲醇衍生物开始，进行吡啶醇的二聚或聚合反应，以产生新的产物。本发明的过程具有以下特点：可以在有或无溶剂的情况下进行，可以使用温度作为催化剂，反应可以或不能通过催化剂（酸或碱）进行催化，所得产物可以容易地生产和分离，从吡啶醇开始，可以通过单步反应产生所得的乙烯二醇，与先前容易氧化的其他化合物相比，作为起始化合物使用的吡啶甲醇衍生物不易氧化，其处理更容易，由乙烯二醇部分产生的产品可以用作抗氧化剂，因为它们具有作为自由基清除剂的能力。
• Klosa, Journal fur praktische Chemie (Leipzig 1954), 1959, vol. <4> 9, p. 289
  作者：Klosa

  DOI：——

  日期：——
• �ber eine der Benzils�ureumlagerung analoge Reaktion in der Pyridinreihe
  作者：Josef Klosa

  DOI：10.1007/bf00641072

  日期：——

表征谱图