6,7-dimethoxy-2,3-bis(1H-pyrrol-2-yl)quinoxaline | 475476-69-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 英文名称: 6,7-dimethoxy-2,3-bis(1H-pyrrol-2-yl)quinoxaline
• 英文别名: 6,7-dimethoxy-2,3-bis(pyrrol-2'-yl)quinoxaline
• CAS: 475476-69-8
• 化学式: C₁₈H₁₆N₄O₂
• 分子量: 320.351
• InChiKey: IANUMYDTSGFUTO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  75.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  6,7-dimethoxy-2,3-bis(1H-pyrrol-2-yl)quinoxaline 在 盐酸 、 三氯氧磷 作用下， 以 甲醇 、 甲苯 为溶剂， 反应 6.67h， 生成
  参考文献：
  名称：

  Quinoxaline-Bridged Porphyrinoids

  摘要：

  Quinoxaline-bridged porphyrinoids (3), the first macrocycles containing dipyrrolylquinoxaline (DPQ, 1) subunits, were synthesized from the condensation of the diformyl-substituted DPQ derivatives (2) and 1,8-diaminoanthracene. The resulting structures were confirmed by X-ray analyses, which showed encapsulation of CHCl3 molecules within the columnar channels established by the stacked arrangement of the individual macrocycles. The solution phase interactions with fluoride and dihydrogen phosphate anions were studied in the case of the unsubstituted system 3a in CH2Cl(2). The binding affinities for these anions, studied at the tetrabutylammonium salts, were found to be enhanced relative to those of the simple, unsubstituted monomeric DPQ "parent" system (11 a), presumably as the result of the combined effects of preorganization and cooperative binding permitted by the pyrrole NH donor groups. Positive homotropic allosteric anion binding was observed and is ascribed to the structurally coupled nature of the two binding cavities present in the macrocycles. Support for this latter contention came from energy minimization studies.

  DOI：

  10.1021/ja0273750
• 作为产物：
  描述：

  1,2-二(1H-吡咯-2-基)-1,2-乙烷二酮 、 1,2-二甲氧基-4-二硝基苯 在 palladium on activated charcoal 氢气 作用下， 以 乙醇 、 溶剂黄146 为溶剂， 20.0 ℃ 、344.74 kPa 条件下， 反应 68.0h， 以89%的产率得到6,7-dimethoxy-2,3-bis(1H-pyrrol-2-yl)quinoxaline
  参考文献：
  名称：

  首次“加冕”的双吡咯基喹喔啉的合成，结构表征和络合特性

  摘要：

  报道了四个冠取代的二吡咯基喹喔啉1-4的合成。合成中的关键步骤是1,2-二氨基苯并冠与1,2-双（1 H-吡咯-2-基）乙二酮（20）的反应。对18-冠-6-二吡咯基喹喔啉1的单晶X射线衍射分析表明，该分子形成围绕一个水分子的四聚体，其中有不少于10个氢键将超分子结构保持在一起。在15冠-5-二吡咯基喹喔啉2的情况下但是，X射线衍射分析表明该物种以二聚体形式存在于固态中，一个吡咯的NH质子位于相邻冠醚上两个氧原子的氢键结合距离之内。解决了第二个单晶结构2；结果表明，该系统能够配位钾阳离子，从而至少在固态下形成分子间夹心复合物。在[d 6 ]丙酮溶液受体2和同类物1，3和4，还发现复杂的钠和钾阳离子的冠乙醚结合位点内，以1：1的方式通过如判断11 H NMR光谱分析。尽管系统1 - 4似乎氟化物阴离子以及阳离子，无法获得定量的结合亲和力结合1 - 4与呈现的系统的评估用于协作的结合是不可能的氟阴离子。（©Wiley-VCH

  DOI：

  10.1002/1099-0690(200211)2002:22<3768::aid-ejoc3768>3.0.co;2-r

文献信息

• Synthesis, Structural Characterization and Complexation Properties of the First “Crowned” Dipyrrolylquinoxalines
  作者：Gregory J. Kirkovits、Rebecca S. Zimmerman、Michael T. Huggins、Vincent M. Lynch、Jonathan L. Sessler

  DOI：10.1002/1099-0690(200211)2002:22<3768::aid-ejoc3768>3.0.co;2-r

  日期：2002.11

  anedione (20). A single crystal X-ray diffraction analysis of the 18-crown-6-dipyrrolylquinoxaline 1 revealed that this molecule forms a tetramer centered around a single molecule of water, with no fewer than 10 hydrogen bonds holding the supramolecular structure together. In the case of the 15-crown-5-dipyrrolylquinoxaline 2, however, X-ray diffraction analysis revealed that this species exists as

  报道了四个冠取代的二吡咯基喹喔啉1-4的合成。合成中的关键步骤是1,2-二氨基苯并冠与1,2-双（1 H-吡咯-2-基）乙二酮（20）的反应。对18-冠-6-二吡咯基喹喔啉1的单晶X射线衍射分析表明，该分子形成围绕一个水分子的四聚体，其中有不少于10个氢键将超分子结构保持在一起。在15冠-5-二吡咯基喹喔啉2的情况下但是，X射线衍射分析表明该物种以二聚体形式存在于固态中，一个吡咯的NH质子位于相邻冠醚上两个氧原子的氢键结合距离之内。解决了第二个单晶结构2；结果表明，该系统能够配位钾阳离子，从而至少在固态下形成分子间夹心复合物。在[d 6 ]丙酮溶液受体2和同类物1，3和4，还发现复杂的钠和钾阳离子的冠乙醚结合位点内，以1：1的方式通过如判断11 H NMR光谱分析。尽管系统1 - 4似乎氟化物阴离子以及阳离子，无法获得定量的结合亲和力结合1 - 4与呈现的系统的评估用于协作的结合是不可能的氟阴离子。（©Wiley-VCH
• Quinoxaline-Bridged Porphyrinoids
  作者：Jonathan L. Sessler、Hiromitsu Maeda、Toshihisa Mizuno、Vincent M. Lynch、Hiroyuki Furuta

  DOI：10.1021/ja0273750

  日期：2002.11.1

  Quinoxaline-bridged porphyrinoids (3), the first macrocycles containing dipyrrolylquinoxaline (DPQ, 1) subunits, were synthesized from the condensation of the diformyl-substituted DPQ derivatives (2) and 1,8-diaminoanthracene. The resulting structures were confirmed by X-ray analyses, which showed encapsulation of CHCl3 molecules within the columnar channels established by the stacked arrangement of the individual macrocycles. The solution phase interactions with fluoride and dihydrogen phosphate anions were studied in the case of the unsubstituted system 3a in CH2Cl(2). The binding affinities for these anions, studied at the tetrabutylammonium salts, were found to be enhanced relative to those of the simple, unsubstituted monomeric DPQ "parent" system (11 a), presumably as the result of the combined effects of preorganization and cooperative binding permitted by the pyrrole NH donor groups. Positive homotropic allosteric anion binding was observed and is ascribed to the structurally coupled nature of the two binding cavities present in the macrocycles. Support for this latter contention came from energy minimization studies.