3-methoxy-2-methyl-phenazine | 13398-82-8

• 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: 3-methoxy-2-methyl-phenazine
• 英文别名: 2,3-dimethoxyphenazine；2,3-Dimethoxyphenazin；2,3-dimethoxy-phenazine；2,3-Dimethoxy-phenazin；2.3-Dimethoxy-phenazin；2,3-Dimethoxyphenacin
• CAS: 13398-82-8
• 化学式: C₁₄H₁₂N₂O₂
• 分子量: 240.261
• InChiKey: YQIADNJBCIVZAI-UHFFFAOYSA-N

物化性质

• 熔点：
  280-281 °C
• 沸点：
  412.6±15.0 °C(Predicted)
• 密度：
  1.250±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

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

• 作为产物：
  描述：

  4,5-dimethoxy-2-nitrodiphenylamine 在 lead 、 草酸亚铁 作用下， 生成 3-methoxy-2-methyl-phenazine
  参考文献：
  名称：

  Notes - Phenazine Synthesis. VII. Certain Disubstituted Phenazines.

  摘要：

  DOI：

  10.1021/jo01113a621

文献信息

• 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.
• Roemer; Scholl; Budzikiewicz, Zeitschrift fur Naturforschung - Teil A Physik, Physikalische Chemie, Kosmophysik, 1981, vol. 36, # 8, p. 1037 - 1046
  作者：Roemer、Scholl、Budzikiewicz、et al.

  DOI：——

  日期：——
• Tschernezkii, Zhurnal Obshchei Khimii, 1957, vol. 27, p. 2833,2835; engl. Ausg. S. 2869, 2871
  作者：Tschernezkii

  DOI：——

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

  DOI：——

  日期：——