1,4-dichlorophenazine | 2881-86-9

• 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: 1,4-dichlorophenazine
• 英文别名: 2,5-dichlorophenazine；1,4-dichloro-phenazine；1,4-Dichlor-phenazin；1,4-Dichlorphenazin
• CAS: 2881-86-9
• 化学式: C₁₂H₆Cl₂N₂
• 分子量: 249.099
• InChiKey: JBXONTRNJUKZTB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  16
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  25.8
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1,4-dichlorophenazine 在 乙醇 、 氯 、 钯 、 硝基苯 作用下， 生成 1,4,6,9-Tetrachlor-phenazin
  参考文献：
  名称：

  Maffei et al., Gazzetta Chimica Italiana, 1953, vol. 83, p. 812,816

  摘要：

  DOI：
• 作为产物：
  描述：

  3,3,6,6-四氯-1,2-环己二酮 在 吡啶 、 sodium acetate 、 lithium perchlorate 作用下， 以 溶剂黄146 、 N,N-二甲基甲酰胺 、 乙腈 、 苯 为溶剂， 反应 24.0h， 生成 1,4-dichlorophenazine
  参考文献：
  名称：

  A new synthetic route to 1-chlorophenazines. The electrochemical monodechlorination of 3,3,6,6-tetrachloro-1,2-cyclohexanedione as a key step

  摘要：

  A convenient new method for the synthesis of 1-chlorophenazines has been established. The first step involves an almost quantitative electrochemical reduction of 3,3,6,6-tetrachloro-1,2-cyclohexanedione 1 to 3,6,6-trichloro-2-hydroxy-2-cyclohexen-1-one 2. The reaction of 2 with aromatic 1,2-diamines followed by aromatisation through treatment with 2,6-lutidine leads to the title compounds in high yields. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(00)01097-2

文献信息

• An efficient method for the synthesis of 1-chlorophenazines based on the selective cathodic reduction of 3,3,6,6-tetrachloro-1,2-cyclohexanedione
  作者：Antonio Guirado、Alfredo Cerezo、Raquel Andreu、José I. López Sánchez、Delia Bautista

  DOI：10.1016/j.tet.2004.06.089

  日期：2004.8

  An efficient method for the synthesis of 1-chlorophenazines has been established. It is based on the use of 3,6,6-trichloro-2-hydroxy-2-cyclohexen-1-one 4 as a synthetic equivalent of 3-chloro-1,2-benzoquinone 3. The intermediate 4 was prepared in near quantitative yield by electroreductive monodechlorination of 3,3,6,6-tetrachloro-1,2-cyclohexanedione 1, which is an inexpensive and easily available

  已经建立了合成1-氯吩嗪的有效方法。它基于使用3,6,6-三氯-2-羟基-2-环己烯-1-酮4作为3-氯-1,2-苯醌3的合成等价物。通过对3,3,6,6-四氯-1,2-环己二酮1进行电还原单氯化，以接近定量的收率制备中间体4，这是一种廉价且易于获得的原料。4与伯1,2-苯二胺的有效反应提供了相应的1,1,4-三氯-1,2,3,4-四氢吩嗪6通过用2，6-二甲基吡啶处理直接将其芳香化，从而以高收率得到标题化合物。1,1,4-三氯-1,2,3,4-四氢-6-甲基吩嗪6f，8-苯甲酰基-1,1,4-三氯-1,2,3,4-四氢的X射线晶体学结构已确定了-phenazine 6ea和1,7-dichlorophenazine 10db。
• One-Pot Synthesis of 1,4-Dichlorophenazines
  作者：Antonio Guirado、Alfredo Cerezo、M.Carmen Ramírez de Arellano

  DOI：10.1016/s0040-4020(97)00275-5

  日期：1997.4

  An efficient, generally applicable one-pot method for the synthesis of 1,4-dichlorophenazines has been established. The method is based on the use of 3,3,6,6-tetrachloro-1,2-cyclohexanedione 2 as a synthetic equivalent of 3,6-dichloro-1,2-benzoquinone 1. The reaction of 2 with primary 1,2-arylidenediamines followed by treatment with pyridine provides the title compounds in nearly quantitative yields. 1,1,4,4-Tetrachloro-1,2,3,4-tetrahydrophenazines are isolable intermediates. The crystallographic X-ray structure of 7,7'-Bis(1,1,4,4-tetrachloro-1,2,3,4-tetrahydrophenazine) 7 has been determined. (C) 1997 Elsevier Science Ltd.
• Rapid Bergman Cyclization of 1,2-Diethynylheteroarenes
  作者：Chang-Sik Kim、K. C. Russell

  DOI：10.1021/jo980879p

  日期：1998.11.1

  The synthesis and cyclization of acyclic quinoxaline, pyridine, and pyrimidine enediynes (1-3) are described. These compounds were prepared using palladium(0) coupling of trimethylsilyl acetylene to o-dihalo- or o-halotriflic heteroarenes. All compounds were prepared in modest to good yields. The enediynes prepared were shown to undergo Bergman cyclization. Kinetics over a minimum of 3 half-lives were used to construct Arrhenius plots. Pyrimidine 3 was found to have an activation energy of 16.1 kcal/mol. Cyclization of the closest known aromatic analogue, o-diethynylbenzene (15), has E-a = 25.1 kcal/mol (Grissom, J. W.; Calkins, T. L.;McMillen, H. A.; Jiang, Y. J. Org. Chem. 1994, 59, 5833-5835). Pyridine 2 and quinoxaline 1 gave activation energies of 21.5 and 33.6 kcal/mol, respectively. The results illustrate that heteroarenes can be used to activate Bergman cyclization. We expect these compounds to play an important role in furthering the understanding of Bergman cyclization and in aiding the development of new biologically significant enediynes.
• Maffei et al., Gazzetta Chimica Italiana, 1953, vol. 83, p. 327,812
  作者：Maffei et al.

  DOI：——

  日期：——
• Tschernezkii; Kiprianow, Zhurnal Obshchei Khimii, 1953, vol. 23, p. 1743,1749;engl.Ausg.S.1839,1843
  作者：Tschernezkii、Kiprianow

  DOI：——

  日期：——

表征谱图