2-formyl-5,10-dimethyl-5,10-dihydrophenazine | 31102-98-4

• 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-formyl-5,10-dimethyl-5,10-dihydrophenazine
• 英文别名: 5,10-Dimethyl-2-formyl-5,10-dihydrophenazine；5,10-dimethylphenazine-2-carbaldehyde
• CAS: 31102-98-4
• 化学式: C₁₅H₁₄N₂O
• 分子量: 238.289
• InChiKey: GLZPLISRORBLBA-UHFFFAOYSA-N

物化性质

• 熔点：
  83 °C
• 沸点：
  430.4±44.0 °C(Predicted)
• 密度：
  1.192±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  23.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-formyl-5,10-dimethyl-5,10-dihydrophenazine 在 哌啶 、 phosphorus pentoxide 、 potassium carbonate 、 对苯二酚 作用下， 以 乙醇 、 二氯甲烷 、 苯 为溶剂， 反应 3606.0h， 生成 2-[2-(5,10-dihydro-5,10-dimethylphenazinyl)]-1,8a-dihydro-1,1-azulenedicarbonitrile
  参考文献：
  名称：

  Spreitzer, Hubert; Daub, Joerg, Chemistry - A European Journal, 1996, vol. 2, # 9, p. 1150 - 1158

  摘要：

  DOI：
• 作为产物：
  描述：

  (5,10-dimethylphenazin-2-yl)methylidene-dimethylazanium 、 水 生成 2-formyl-5,10-dimethyl-5,10-dihydrophenazine
  参考文献：
  名称：

  POKHODENKO, V. D.;KOSHECHKO, V. G.;INOZEMTSEV, A. N., J. CHEM. SOC. CHEM. COMMUN., 1985, N 2, 72-73

  摘要：

  DOI：

文献信息

• Cyclohepta[<i>b</i>][1,4]benzothiazines and Their Diazine Analogues. 2. Formation and Properties of Cyclohepta[<i>b</i>]quinoxalines
  作者：Kimio Shindo、Sumio Ishikawa、Tetsuo Nozoe

  DOI：10.1246/bcsj.62.1158

  日期：1989.4.15

  2-Chloro- or 2-methoxytropone reacts with o-phenylenediamine to give 2-(o-aminoanilino)tropone, which upon heating provides 6H-cyclohepta[b]quinoxaline (10a). Upon acidification, 10a reversibly gives a green cation, 9a. 10a is easily converted, especially under basic conditions, into the oxidative dimer 16a, which reproduces 9a by reduction with Zn in acetic acid. The isopropyl derivatives of these compounds are prepared by the same method from 5-isopropyl-2-methoxytropone. The 5-methyl (21a) and 5,11-dimethyl derivatives 23 are made by the reaction of 2-chloro- or 2-methoxytropone with N-methyl- and N,N′-dimethyl-o-phenylenediamines. However, the methylation of 21a with methyl fluorosulfate affords 5,11-dihydro-8,11-dimethyl-6H-cyclohepta[b]quinoxaline-5,6-sultone. H2O2 oxidation of 10a mainly gives 16a in addition to a small quantity of 6H-cyclohepta[b]quinoxalin-6-one. Compound 21a is stable under basic conditions, but 23 rearranges under alkaline conditions to give, among other unidentified products, N-methyl-N-[o-(methylamino)phenyl]benzamide and 5,10-dihydro-5,10-dimethyl-2-phenazinecarbaldehyde. Reactions of title compounds with alkali and hydrogen peroxide are compared with those of O- and S-analogues.

  2-氯或2-甲氧基脱氢松香与邻苯二胺反应生成2-(邻氨基苯基氨基)脱氢松香，随着加热生成6H-环七[b]喹喏啉(10a)。在酸性环境下，10a 可逆地生成绿色阳离子9a。10a 易于转化，特别是在碱性条件下，生成氧化二聚体16a，16a通过与醋酸中的Zn还原可再生9a。这些化合物的异丙基衍生物是通过5-异丙基-2-甲氧基脱氢松香用同样的方法制备的。5-甲基(21a)和5,11-二甲基衍生物23是通过2-氯或2-甲氧基脱氢松香与N-甲基和N,N'-二甲基邻苯二胺反应制得的。然而，用氟甲基硫酸盐对21a进行甲基化反应则得到5,11-二氢-8,11-二甲基-6H-环七[b]喹喏啉-5,6-磺酸酯。10a的H2O2氧化反应主要生成16a，外加少量的6H-环七[b]喹喏啉-6-酮。化合物21a在碱性条件下稳定，但23在碱性条件下发生重排，生成包括N-Methyl-N-[o-(甲基氨基)苯基]苯胺和5,10-二氢-5,10-二甲基-2-苯嗪羧醛在内的其他未鉴定产品。标题化合物与碱和氢过氧化物的反应与O-和S-类比的反应进行比较。
• Electrochromic compounds
  申请人：Gentex Corporation

  公开号：US05998617A1

  公开（公告）日：1999-12-07

  An improved electrochromic device, the device incorporating an electrochromic medium that comprises at least three electroactive materials having absorption spectra that add together such that the color of the electrochromic medium can be pre-selected by individually choosing the concentrations of the at least three electroactive materials. The electrochromic medium generally maintains the pre-selected perceived color throughout its normal range of voltages when used in an electrochromic device. The at least three electroactive materials include at least one electrochemically reducible material (cathodic material), at least one electrochemically oxidizable material (anodic material) and at least one additional electroactive material which may be either an anodic or cathodic material. Thus, there are always three electroactive materials present in the medium, with at least two either being anodic or cathodic materials. The pre-selected color may be chosen from a wide variety of colors and may be, for example, red, orange, yellow, green, blue, purple. For electrochromic mirrors for motor vehicles, a presently preferred color is gray.

  一种改进的电致色变装置，该装置包括一种电致色变介质，该介质包含至少三种具有吸收光谱的电活性材料，这些吸收光谱相互叠加，使得电致色变介质的颜色可以通过单独选择至少三种电活性材料的浓度来预先选择。当在电致色变装置中使用时，该电致色变介质通常在其正常电压范围内保持预选感知颜色。至少三种电活性材料包括至少一种电化学可还原材料（阴极材料），至少一种电化学可氧化材料（阳极材料）和至少一种其他电活性材料，该其他电活性材料可以是阳极或阴极材料。因此，介质中始终存在三种电活性材料，其中至少有两种材料为阳极或阴极材料。预选的颜色可以选择各种各样的颜色，例如红色、橙色、黄色、绿色、蓝色、紫色。对于汽车电致色变镜，目前首选的颜色是灰色。
• 吩嗪类金属富勒烯衍生物、制法及激发态寿命的调控方法
  申请人：北京福纳康生物技术有限公司

  公开号：CN107337670A

  公开（公告）日：2017-11-10

  本发明公开了吩嗪类金属富勒烯衍生物、制法及激发态寿命的调控方法。本发明中的金属富勒烯衍生物是经过加成反应，在金属富勒烯表面修饰具有给电子特性的吩嗪类化合物得到的，通过此方法可以调控金属富勒烯的激发态寿命。采用飞秒瞬态吸收光谱表征吩嗪类金属富勒烯衍生物的激发态动力学性质，然后通过数据计算拟合比较激发态寿命的变化。提供的吩嗪类金属富勒烯衍生物结构新颖，具有长寿命激发态，可简便、高效、灵敏调控金属富勒烯的激发态特性，此类吩嗪类金属富勒烯衍生物可用于光物理和光化学过程中，解决了现有金属富勒烯激发态寿命短、调控方式不明确、调控手段复杂、灵敏度差的问题。
• Cation radicals as intermediates in the Vilsmeier–Haack formylation
  作者：Vitaly D. Pokhodenko、Vyacheslav G. Koshechko、Andrei N. Inozemtsev

  DOI：10.1039/c39850000072

  日期：——

  Cation radicals were found to be transient species in the formylation of N-substituted dihydrophenazines and their concentration at any one time may be as high as 50–90% of the initial substrate.

  在N取代的二氢吩嗪的甲酰化过程中，发现阳离子自由基是瞬态物质，在任何时候它们的浓度都可能高达初始底物的50-90％。
• Anion‐Dependent Redox Chemistry of p‐Type Poly(vinyldimethylphenazine) Cathode Materials
  作者：An Duan、Ziheng Wang、Xiaoyu Huang、Yongjun Li

  DOI：10.1002/anie.202302754

  日期：2023.6.12

  Metal‐free organic electrode materials have attracted vast research attention owing to their designable structures and tunable electrochemical properties. Although n‐type cathode materials could be used in various metal‐ion batteries, p‐type ones with high potential can deliver high energy density. Herein, we report a new p‐type polymeric cathode material, poly(2‐vinyl‐5,10‐dimethyl‐dihydrophenazine) (PVDMP), with a theoretical capacity of 227 mAh g⁻¹. PVDMP featuring two‐step redox reaction will be doped by two anions to maintain electroneutrality during oxidation, which resulted in an anion‐dependent electrochemical behavior of PVDMP‐based cathode. The suitable dopant anion for PVDMP was selected and the doping mechanism was confirmed. Under the optimized condition, PVDMP cathode can deliver a high initial capacity of 220 mAh g⁻¹ at 5 C and even remains 150 mAh g⁻¹ after 3900 cycles. This work not only provides a new kind of p‐type organic cathode materials but also deepens the understanding of its anion‐dependent redox chemistry.

  摘要 无金属有机电极材料因其可设计的结构和可调整的电化学特性而引起了广泛的研究关注。虽然 n 型阴极材料可用于各种金属离子电池，但具有高电势的 p 型阴极材料可提供高能量密度。在此，我们报告了一种新型 p 型聚合物阴极材料--聚（2-乙烯基-5,10-二甲基二氢吩嗪）（PVDMP），其理论容量为 227 mAh g-1。PVDMP 具有两步氧化还原反应，在氧化过程中会掺杂两种阴离子以保持电中性，这导致了 PVDMP 阴极的电化学行为与阴离子有关。选择了适合 PVDMP 的掺杂阴离子，并确认了掺杂机理。在优化条件下，PVDMP 阴极在 5 C 时可提供 220 mAh g-1 的高初始容量，甚至在循环 3900 次后仍可保持 150 mAh g-1 的容量。这项工作不仅提供了一种新型 p 型有机阴极材料，而且加深了对其阴离子依赖性氧化还原化学的理解。