3,6-dimethoxy-9-(4-methoxyphenyl)-carbazole | 56525-76-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: 3,6-dimethoxy-9-(4-methoxyphenyl)-carbazole
• 英文别名: 3,6-Dimethoxy-9-(4-methoxyphenyl)carbazole
• CAS: 56525-76-9
• 化学式: C₂₁H₁₉NO₃
• 分子量: 333.387
• InChiKey: CNHBKKWGENXQLH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  25
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  32.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  tris(4-methoxyphenyl)amine radical anion 以 二氯甲烷 为溶剂， 生成 3,6-dimethoxy-9-(4-methoxyphenyl)-carbazole
  参考文献：
  名称：

  Excited-State Behavior of Thermally Stable Radical Ions

  摘要：

  The excited states of several families of thermally stable radical ions in solution are surveyed by transient absorption and steady-state fluorescence spectroscopy to determine prevalent deactivation mode(s). Of the species investigated, weak fluorescence can be observed only for substituted triarylamine radical cations, presumably from their lowest excited doublet states. The primary excited-state deactivation pathway for radical anions of the quinones, aryl ketones, and cyanoarene hydrocarbons examined here is internal conversion from the lowest excited doublet state to the ground-state doublet. The efficiency of this deactivation mode arises typically from a low D-0-D-1 energy gap, as demonstrated by near-infrared absorbance in each species. Contrary to a prior literature report, the 9,10-anthraquinone radical anion and the 9,10-dicyanoanthracene radical anion are nonluminescent in solution. Luminescent side products generated in ground-state reactions of these radical anions are identified as 9,9-bianthrone dianion (from the dimerization and deoxygenation of the anthraquinone radical anion) and 10-cyanoanthrolate (from the reaction of dicyanoanthracene radical anion with molecular oxygen).

  DOI：

  10.1021/j100053a011

文献信息

• A Visible-Light-Mediated Synthesis of Carbazoles
  作者：Augusto C. Hernandez-Perez、Shawn K. Collins

  DOI：10.1002/anie.201306920

  日期：2013.11.25

  The photosynthetic preparation of N‐aryl‐ and N‐alkyl‐bearing carbazoles utilizes continuous flow, visible light, and an in situ formed Cu‐based sensitizer (see picture). The method is mild and efficient, and allows the straightforward synthesis of a variety of carbazoles with different substituents, heterocycles, and complex carbon architectures.

  光合制备的ñ -芳基-和ñ -烷基轴承咔唑利用连续流，可见光，和原位形成的铜基增敏剂（参照图片）。该方法温和高效，可直接合成具有不同取代基，杂环和复杂碳结构的多种咔唑。
• A hydrazine-free photoredox catalytic synthesis of azines by reductive activation of readily available oxime esters
  作者：Jonathan Schütte、Daria Corsi、Wolfgang Haumer、Simon Schmid、Jonas Žurauskas、Joshua P. Barham

  DOI：10.1039/d4gc00804a

  日期：——

  a novel, hydrazine-free photoredox catalyzed platform for azine synthesis using mild, simple reaction conditions. While previous energy transfer activations of oxime esters lead to decarboxylation of the O-auxiliary and radical combination with the iminyl radical, the reductive electron transfer strategy herein affords high yields of azines using only a triarylamine organophotocatalyst and no additives

  在此，我们提出了一种新型的、无肼的光氧化还原催化平台，用于使用温和、简单的反应条件合成吖嗪。虽然先前的肟酯的能量转移活化导致O-辅助基团和自由基与亚胺基的组合脱羧，但本文的还原电子转移策略仅使用三芳胺有机光催化剂且不使用添加剂即可提供高产率的吖嗪。通过连续流反应器很容易实现放大。机理研究表明光催化剂和基材的预组装是实现高效、选择性 N-N 亚氨基自由基偶联的关键。
• Photochemical Electrocyclization of Thermally Stable Triarylamine Radical Cations
  作者：David T. Breslin、Marye Anne Fox

  DOI：10.1021/jo00103a069

  日期：1994.12
• Photochemical Synthesis of Carbazoles Using an [Fe(phen)₃](NTf₂)₂/O₂ Catalyst System: Catalysis toward Sustainability
  作者：Shawn Parisien-Collette、Augusto C. Hernandez-Perez、Shawn K. Collins

  DOI：10.1021/acs.orglett.6b02456

  日期：2016.10.7

  An increasingly sustainable photochemical synthesis of carbazoles was developed using a catalytic system of Fe(phen)(3)(NTf2)(2)/O-2 under continuous flow conditions and was demonstrated on gram scale using a numbering-up strategy. Photocyclization of triaryl and diarylamines into the corresponding carbazoles occurs in general in higher yields than with previously developed photocatalysts.
• The Double N-Arylation of Primary Amines: Toward Multisubstituted Carbazoles with Unique Optical Properties
  作者：Kyoko Nozaki、Keita Takahashi、Koji Nakano、Tamejiro Hiyama、Hong-Zhi Tang、Michiya Fujiki、Shigehiro Yamaguchi、Kohei Tamao

  DOI：10.1002/anie.200250648

  日期：2003.5.9