11-nitrodibenzo[a,c]phenazine | 4661-57-8

• 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: 11-nitrodibenzo[a,c]phenazine
• 英文别名: 11-nitro-dibenzo[a,c]phenazine；11-Nitro-dibenzo[a,c]phenazin；11-Nitro-dibenzophenazin；11-Nitro-1,2:3,4-dibenzophenazin；11-Nitrodibenzo(a,c)phenazine；11-nitrophenanthro[9,10-b]quinoxaline
• CAS: 4661-57-8
• 化学式: C₂₀H₁₁N₃O₂
• 分子量: 325.326
• InChiKey: LJVWTGJLCXLVOI-UHFFFAOYSA-N

物化性质

• 熔点：
  254-255 °C(Solv: ethanol (64-17-5))
• 沸点：
  617.9±20.0 °C(Predicted)
• 密度：
  1.451±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  25
• 可旋转键数：
  0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  71.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  11-nitrodibenzo[a,c]phenazine 在 potassium tert-butylate 、 1,1,1-三甲基碘化肼 作用下， 以 二甲基亚砜 为溶剂， 以32%的产率得到11-Nitrophenanthro[9,10-b]quinoxalin-10-amine
  参考文献：
  名称：

  Ferrocene-Based Heteroditopic Receptors Displaying High Selectivity toward Lead and Mercury Metal Cations through Different Channels

  摘要：

  The synthesis and electrochemical, optical, and ion-sensing properties of ferrocene-imidazophenazine dyads are presented. Dyad 4 behaves as a highly selective chemosensor molecule for Pb2+ cations in CH3-CN/H2O (9:1). The emission spectrum (lambda(exc) = 317 nm) undergoes an important chelation-enhanced fluorescence effect (CHEF = 47) in the presence of Pb2+ cations, a new low-energy band appeared at 502 nm, in its UV/vis spectrun, and the oxidation redox peak is anodically shifted (Delta E-1/2 = 230 mV). The presence of Hg2+ cations also induced a perturbation of the redox potencial although in less extension, than those found with Pb2+ cations. Dyad 7, bearing two fused pyridine rings, has shown its ability for sensing Hg2+ cations selectively through three channels: electrochemical, optical, and fluorescent; the oxidation redox peak is anodically shifted (Delta(1/2) = 200 mV), a new low-energy band of the absorption spectrum appeared at 485 nm, and the emission spectrum (lambda(exc) = 340 nm) is red-shifted by 32 nm accompanied by a remarkable chelation-enhanced fluorescent effect (CHEF = 165). Linear sweep voltammetry revealed that Cu2+ cations induced oxidation of the ferrocene unit in both dyads. H-1 NMR studies have been carried out to obtain information about the molecular sites which are involved in the binding process.

  DOI：

  10.1021/jo102243e
• 作为产物：
  描述：

  2,4-二硝基苯胺 在 ammonium sulfide 、 溶剂黄146 作用下， 生成 11-nitrodibenzo[a,c]phenazine
  参考文献：
  名称：

  Heim, Chemische Berichte, 1888, vol. 21, p. 2306

  摘要：

  DOI：

文献信息

• A new facet of the reaction of nitro heteroaromatic compounds with ethyl isocyanoacetate
  作者：Takashi Murashima、Ken-ichi Fujita、Kazuo Ono、Takuji Ogawa、Hidemitsu Uno、Noboru Ono

  DOI：10.1039/p19960001403

  日期：——

  heteroarenes react with ethyl isocyanoacetate in the presence of 1,8-diazabicyclo[5.4.0]undecene (DBU) to give pyrroles or pyrimidine N-oxide depending on the structure of the starting nitro compounds. For example, 4-nitro-2,1,3-benzothiadiazole 3a reacted with ethyl isocyanoacetate to give ethyl 2,1,3-benzothiadiazole[3,4-c]pyrrole-2-carboxylate 4a (33%), while a similar reaction with 5-nitro-2,1,3-benzothiadiazole

  在1,8-二氮杂双环[5.4.0]十一碳烯（DBU）存在下，硝基杂芳烃与异氰基乙酸乙酯反应生成吡咯或嘧啶N-氧化物，具体取决于起始硝基化合物的结构。例如，4-硝基-2,1,3-苯并噻二唑3a与异氰基乙酸乙酯反应生成2,1,3-苯并噻二唑[3,4- c ]吡咯-2-羧酸乙酯4a（33％），与5-硝基-2,1,3-苯并噻二唑3b反应，得到相应的化合物4b（21％），为唯一产物。提出了这些反应的合理机制。
• Zirconium triflate: An efficient catalyst for the synthesis of quinolines and quinoxalines
  作者：Eskandar Kolvari、Mohammad Ali Zolfigol、Nadiya Koukabi、Maryam Gilandust、Abdol-Vahid Kordi

  DOI：10.1007/s13738-013-0252-2

  日期：2013.12

  An environmentally friendly method is described for the preparation of substituted quinoline and quinoxaline derivatives using Zr(OTf)4 as an efficient catalyst. The method is based on using 1,3-diketones, ketones and 2-aminoaryl ketones under solvent-free conditions and also on using 1,2-diketone, 1,2-diamine in EtOH/H2O at room temperature for quinloine and quinoxaline synthesis, respectively. The advantages in using this method, include its environmental friendliness, simple operating process and good yields.

  一种环保的方法被描述用于制备取代喹啉和喹喔啉衍生物，使用了Zr(OTf)4作为高效催化剂。该方法基于在无溶剂条件下使用1,3-二酮、酮和2-氨基芳基酮，以及在室温下使用1,2-二酮、1,2-二胺在EtOH/H2O中分别进行喹啉和喹喔啉的合成。使用这种方法的优势包括其环境友好性、操作过程简单和良好的产率。
• In water organic synthesis: Introducing itaconic acid as a recyclable acidic promoter for efficient and scalable synthesis of quinoxaline derivatives at room temperature
  作者：Kashyap J. Tamuli、Shyamalendu Nath、Manobjyoti Bordoloi

  DOI：10.1002/jhet.4231

  日期：2021.4

  Substituted quinoxaline derivatives are traditionally synthesized by co‐condensation of various starting materials. Herein, we describe a novel environmentally benign in water synthetic route for the synthesis of structurally and electronically diverse ninety quinoxalines with readily available substituted o‐phenylenediamine and 1,2‐diketones using cheap and biodegradable itaconic acid as a mild acid

  取代的喹喔啉衍生物传统上是通过各种起始原料的共缩合反应合成的。在本文中，我们描述了一种新型的环境友好的水合成路线，用于合成结构和电子形式多样的90喹喔啉类化合物，并容易获得取代的邻氨基苯甲酸。苯二胺和1,2-二酮在1小时内使用廉价且可生物降解的衣康酸作为温和的酸性促进剂。该反应在室温下进行，该过程通过环缩合反应进行，然后获得上述含氮杂环加合物，而无需进行柱色谱分离，总收率不超过96％。催化剂的简单性，高效率和可重复使用性将该反应条件称为“绿色合成”，这使其可用于克级至克级的合成转化中。
• [BBSA-DBN][HSO4]: a novel –SO3H functionalized Bronsted acidic ionic liquid for easy access of quinoxalines
  作者：Megha U. Patil、Sachinkumar K. Shinde、Sandip P. Patil、Suresh S. Patil

  DOI：10.1007/s11164-020-04227-3

  日期：2020.11

  Abstract A novel –SO3H difunctionalized Bronsted acidic ionic liquid (BAIL) 1, 5-bis (butanesulphonic acid)-diazobicyclo [4,3,0] non-5-enium hydrogen sulphate [BBSA-DBN][HSO4] is introduced for efficient synthesis of quinoxalines via condensation of substituted 1,2-diketones and various aromatic 1,2-diamines. It could serve as a dual functional catalyst for these reactions. This method has the advantages

  摘要 新型–SO 3 H双官能化布朗斯台德酸性离子液体（BAIL）1，5-双（丁磺酸）-重氮双环[4,3,0]非-5-氢硫酸氢盐[BBSA-DBN] [HSO 4引入[1]通过取代的1，2-二酮和各种芳族1，2-二胺的缩合有效合成喹喔啉。它可以用作这些反应的双重功能催化剂。该方法的优点是反应条件温和，收率高，反应时间短，后处理容易，非色谱分离，环境友好。该方案为生产喹喔啉提供了一种有效且环保的替代方法，并扩展了有机合成中苯的化学利用。此室温衍生离子液体是高酸性是由于两个-SO的存在3个H基团和两个HSO 4 -的阴离子。此外，IL [BBSA-DBN] [HSO 4可以很容易地被回收并至少重复使用五次而不会改变其催化活性。IL [BBSA-DBN] [HSO 4 ]的形成通过1 H，13 C NMR光谱技术确认。 图形摘要
• Protic ionic liquids: a lucid, rational tool for synthesis of phthalazinediones, quinoxalines and benzopyrans
  作者：A. G. Mulik、D. R. Chandam、D. R. Patil、P. P. Patil、G. N. Mulik、S. T. Salunkhe、M. B. Deshmukh

  DOI：10.1007/s11164-015-2014-5

  日期：2015.12

  Protic ionic liquids (PILs), which are easily produced through the combination of a Brønsted acid and Brønsted base, such as [Mim]Ac and 1,4-diazabicyclo[2.2.2]octane (DABCO):AcOH:H2O (1:1:3), were found to be lucid, tunable tool for synthesis of various heterocyclic motifs such as phthalazinediones, quinoxalines and benzopyrans. These PILs were found to be efficient for synthesis of diverse heterocyclic derivatives, along with demonstrating noteworthy aspects such as high yields, isolation of pure products without column chromatography and recyclable reaction media.

  质子离子液体（PILs）是通过布朗斯特酸和布朗斯特碱的结合容易生成的，例如[Mim]Ac和1,4-二氮杂双环[2.2.2]辛烷（DABCO）：AcOH:H2O（1:1:3）。研究发现，它们是合成多种杂环结构（如邻苯二甲酰亚胺、喹喔啉和苯并吡喃）的明晰且可调的工具。这些PILs在合成多样化的杂环衍生物方面表现出高效，并且具有显著特点，如高产率、能够在不使用柱层析的情况下分离纯产品以及可回收的反应介质。