2,3-dimethylphenazine | 6479-88-5

• 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: 2,3-dimethylphenazine
• 英文别名: 2,3-dimethyl-phenazine；2,3-Dimethyl-phenazin；2,3-Dimethylphenazin
• CAS: 6479-88-5
• 化学式: C₁₄H₁₂N₂
• mdl: MFCD01861444
• 分子量: 208.263
• InChiKey: AXTJIDAKPWEJCR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  16
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.142
• 拓扑面积：
  25.8
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  3,4-二甲基苯酚 在 potassium nitrososulfonate 、 氯仿 作用下， 生成 2,3-dimethylphenazine
  参考文献：
  名称：

  Teuber; Staiger, Chemische Berichte, 1955, vol. 88, p. 802,813

  摘要：

  DOI：

文献信息

• Electro-Oxidative Synthesis of Phenazines
  作者：Deepak Sharma、Namrata Kotwal、Pankaj Chauhan

  DOI：10.1021/acs.orglett.3c01270

  日期：2023.5.26

  electro-oxidative synthesis as the general protocol for procuring phenazines under mild reaction conditions. Using aerial oxygen as an oxidant, inexpensive electrolyte, and electrodes, a diverse range of phenazines have been accessed in good yields via the ring contraction of 10,11-dihydro-5H-dibenzo[b,e][1,4]diazepines. In addition, the syntheses of phenazines and diamino phenazines via direct electro-oxidation

  我们在此公开电氧化合成作为在温和反应条件下获得吩嗪的一般方案。使用空气中的氧气作为氧化剂、廉价的电解质和电极，通过 10,11-dihydro-5 H -dibenzo[ b,e ][1,4]diazepines的环收缩以良好的收率获得了多种吩嗪. 此外，还分别通过二氢吩嗪的直接电氧化和邻苯二胺的电二聚反应合成了吩嗪和二氨基吩嗪。
• Potential Chemopreventive Agents Based on the Structure of the Lead Compound 2-Bromo-1-hydroxyphenazine, Isolated from <i>Streptomyces</i> Species, Strain CNS284
  作者：Martin Conda-Sheridan、Laura Marler、Eun-Jung Park、Tamara P. Kondratyuk、Katherine Jermihov、Andrew D. Mesecar、John M. Pezzuto、Ratnakar N. Asolkar、William Fenical、Mark Cushman

  DOI：10.1021/jm1011066

  日期：2010.12.23

  The isolation of 2-bromo-1-hydroxyphenazine from a marine Streptomyces species, strain CNS284, and its activity against NF-kappa B, suggested that a short and flexible route for the synthesis of this metabolite and a variety of phenazine analogues should be developed. Numerous phenazines were subsequently prepared and evaluated as inducers of quinone reductase I (QR1) and inhibitors of quinone reductase 2 (QR2), NF-kappa B, and inducible nitric oxide synthase (iNOS). Several of the active phenazine derivatives displayed IC50 values vs QR1 induction and QR2 inhibition in the nanomolar range, suggesting that they may find utility as cancer chemopreventive agents.
• Diepolder, Chemische Berichte, 1909, vol. 42, p. 2922
  作者：Diepolder

  DOI：——

  日期：——
• Transition-Metal-Free Tandem Oxidative Removal of Benzylic Methylene Group by C–C and C–N Bond Cleavage Followed by Intramolecular New Aryl C–N Bond Formation under Radical Conditions
  作者：Joydev K. Laha、K. S. Satyanarayana Tummalapalli、Ankur Gupta

  DOI：10.1021/ol501766m

  日期：2014.9.5

  A novel tandem oxidative conversion of 10,11-dihydro-5H-dibenzo[b,e][1,4]diazepines to phenazines has been achieved under transition-metal-free, mild conditions using K2S2O8 or DDQ as the oxidizing agent. The transformation proceeds through oxidative removal of a benzylic methylene group by C-C and C-N bond cleavage followed by a new aryl C-N bond formation under radical conditions.
• [EN] ANTIMICROBIAL PHENAZINE COMPOUNDS<br/>[FR] COMPOSES DE PHENAZINE ANTIMICROBIENS
  申请人：——

  公开号：WO1998027969A2

  公开（公告）日：1998-07-02

  [EN] Phenazine compounds having antimicrobial activity are described. The phenazine compounds can be phenazine N-oxides, including phenazine-5,10-dioxides, which may optionally be substituted at one or more positions, preferably the 7- and/or 8-positions of the phenazine nucleus. Also described are methods for treating microbial infections, and methods for inhibiting the growth of a microbial cell. The microbes treated or inhibited can be multidrug resistant.
  [FR] Composés de phénazine à activité antimicrobienne, pouvant être des N-oxydes de phénazine, y compris des 5,10-dioxydes de phénazine, qui peuvent être éventuellement substitués à une ou plusieurs positions, de préférence les positions 7- et/ou 8- du noyau phénazine. Des méthodes de traitement d'infections microbiennes et des méthodes permettant d'inhiber la croissance d'une cellule microbienne sont également décrites. Les microbes traités ou inhibés peuvent présenter une résistance multiple aux médicaments.