1,4-Dimethoxy-phenazin | 13860-45-2

• 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-Dimethoxy-phenazin
• 英文别名: 1,4-Dimethoxyphenazine
• CAS: 13860-45-2
• 化学式: C₁₄H₁₂N₂O₂
• 分子量: 240.261
• InChiKey: XSNGJHHLSHMCND-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  44.2
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1,4-Dimethoxy-phenazin 在 氢溴酸 、 sodium acetate 、 溶剂黄146 作用下， 生成 1,4-diacetoxy-phenazine
  参考文献：
  名称：

  Yosioka; Otomasu, Pharmaceutical Bulletin, 1954, vol. 2, p. 53,57

  摘要：

  DOI：
• 作为产物：
  描述：

  6,9-dimethoxy-1,2,3,4-tetrahydro-phenazine 在 palladium on activated charcoal 作用下， 生成 1,4-Dimethoxy-phenazin
  参考文献：
  名称：

  King et al., Journal of the Chemical Society, 1949, p. 3012,3016

  摘要：

  DOI：

文献信息

• Decomposition pathways and mitigation strategies for highly-stable hydroxyphenazine flow battery anolytes
  作者：Nadeesha P. N. Wellala、Aaron Hollas、Kaining Duanmu、Vijayakumar Murugesan、Xin Zhang、Ruozhu Feng、Yuyan Shao、Wei Wang

  DOI：10.1039/d1ta03655f

  日期：——

  undergoes desulfonation and reduction of a phenolic C–O bond to yield a mixture of 7/8-hydroxyphenazine-2-sulfonic acid, as well as hydrogenation of the aromatic ring system. Density functional theory (DFT) analysis of the charged DHPS, its ring-hydrogenated products, and variably substituted hydroxy phenazines has led to the development of a series of dihydroxylated phenazine isomers which provide insight

  水性有机氧化还原液流电池是一种很有前途的大规模储能技术。氧化还原活性有机分子的稳定性越来越被认为是主要障碍之一。在延长液流电池循环过程中，7,8-二羟基吩嗪-2-磺酸 (DHPS) 发生脱磺化和酚类 C-O 键的还原反应，生成 7/8-羟基吩嗪-2-磺酸的混合物，并氢化芳香环系统。带电 DHPS、其环氢化产物和可变取代的羟基吩嗪的密度泛函理论 (DFT) 分析导致了一系列二羟基吩嗪异构体的开发，这些异构体提供了对取代模式对溶解性和稳定性的影响的深入了解。合成了七种二羟基吩嗪 (DHP) 异构体及其溶解度，电化学性能、液流电池循环性能和降解途径已被研究。根据理论和实验结果，1、4、6 和 9 位的羟基取代产生高度稳定的衍生物，而 2、3、7 和 8 位的取代产生不稳定的衍生物。1,4- 和 1,6-DHP 与亚铁/铁氰化物结合的流通池实现了高稳定性，时间容量损失分别为每天 0.029% 和 0
• Phenazines and Benzcinnolines
  作者：P. Z. SLACK、R. SLACK

  DOI：10.1038/160437a0

  日期：1947.9

  A number of attempts have been made to devise general methods for the synthesis of phenazines1,2,3; but in a series of researches carried out during 1945–46 we found that most of the well-known methods failed in the case of some di-alkoxyphenazines. On the other hand, comparatively good results were obtained using the little-known reaction of Waterman and Vivian4, which depends on the treatment of a 2-nitro-or 2:2′-dinitrodiphenylamine with an ‘Oxygen acceptor’ such as reduced iron, lead or charcoal at a high temperature. In simple cases the reaction presumably proceeds, as suggested by the original authors, through the elimination of oxygen and water, but in the case of the 2: 2′-dinitro derivatives the course of the condensation is more obscure.

  已经有多次尝试制定合成苯嗪的通用方法；但是在1945年至1946年期间进行的一系列研究中，我们发现大多数知名的方法在某些二烷氧基苯嗪的情况下失败。另一方面，使用Waterman和Vivian不太知名的反应取得了相对较好的结果，该反应依赖于在高温下用还原铁、铅或炭等“氧受体”处理2-硝基或2,2'-二硝基二苯胺。在简单情况下，反应可能如原作者所建议的那样，通过去除氧气和水进行，但在2,2'-二硝基衍生物的情况下，缩合过程则更为复杂。
• 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.
• King et al., Journal of the Chemical Society, 1949, p. 3012,3016
  作者：King et al.

  DOI：——

  日期：——
• Yosioka; Otomasu, Pharmaceutical Bulletin, 1954, vol. 2, p. 53,57
  作者：Yosioka、Otomasu

  DOI：——

  日期：——