2,7-二甲氧基-9-苯基咔唑 | 592551-52-5

• 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
• 中文名称: 2,7-二甲氧基-9-苯基咔唑
• 英文名称: 2,7-dimethoxy-9-phenylcarbazole
• 英文别名: 2,7-Dimethoxy-9-phenyl-9H-carbazole
• CAS: 592551-52-5
• 化学式: C₂₀H₁₇NO₂
• 分子量: 303.36
• InChiKey: JAYXWWFBMRWOQH-UHFFFAOYSA-N

物化性质

• 沸点：
  481.8±38.0 °C(Predicted)
• 密度：
  1.15±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  23
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  23.4
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  双三甲基硅氧基甲基硅烷 、 2,7-二甲氧基-9-苯基咔唑 在 三(五氟苯基)硼烷 作用下， 以 甲苯 为溶剂， 以85%的产率得到Trimethyl-[methyl-[7-[methyl-bis(trimethylsilyloxy)silyl]oxy-9-phenylcarbazol-2-yl]oxy-trimethylsilyloxysilyl]oxysilane
  参考文献：
  名称：

  Liquid Triarylamines: The Scope and Limitations of Piers–Rubinsztajn Conditions for Obtaining Triarylamine–Siloxane Hybrid Materials

  摘要：

  New liquid triarylamine-siloxane hybrid materials are produced using the Piers-Rubinsztajn reaction. Under mild conditions, liquid analogues of conventional and commonly crystalline triarylamines are easily synthesized from readily available or accessible intermediates. Using a diverse selection of triarylamines, we explored the effects of siloxane group and substitution pattern on the physical properties of these materials, and we have demonstrated that relatively large molecular liquids with desirable electrochemical properties can be produced. The interactions between the strongly Lewis acidic catalyst used for this transformation, tris(pentafluorophenyl)borane (BCF), and the Lewis basic triarylamine substrates were studied. Through UV-vis-NIR and F-19 NMR spectroscopy, we have proposed that the catalyst undergoes a reversible redox reaction with the substrates to produce a charge transfer complex. The formation of this charge transfer complex is sensitive to the oxidation potential of the triarylamine and can greatly affect the kinetics of the Piers-Rubinsztajn reaction.

  DOI：

  10.1021/jo2020906
• 作为产物：
  描述：

  4,4'-dimethoxy-2-nitrobiphenyl 在 copper(l) iodide 、 potassium carbonate 、 L-脯氨酸 、 亚磷酸三乙酯 作用下， 以 二甲基亚砜 为溶剂， 反应 18.0h， 生成 2,7-二甲氧基-9-苯基咔唑
  参考文献：
  名称：

  Liquid Triarylamines: The Scope and Limitations of Piers–Rubinsztajn Conditions for Obtaining Triarylamine–Siloxane Hybrid Materials

  摘要：

  New liquid triarylamine-siloxane hybrid materials are produced using the Piers-Rubinsztajn reaction. Under mild conditions, liquid analogues of conventional and commonly crystalline triarylamines are easily synthesized from readily available or accessible intermediates. Using a diverse selection of triarylamines, we explored the effects of siloxane group and substitution pattern on the physical properties of these materials, and we have demonstrated that relatively large molecular liquids with desirable electrochemical properties can be produced. The interactions between the strongly Lewis acidic catalyst used for this transformation, tris(pentafluorophenyl)borane (BCF), and the Lewis basic triarylamine substrates were studied. Through UV-vis-NIR and F-19 NMR spectroscopy, we have proposed that the catalyst undergoes a reversible redox reaction with the substrates to produce a charge transfer complex. The formation of this charge transfer complex is sensitive to the oxidation potential of the triarylamine and can greatly affect the kinetics of the Piers-Rubinsztajn reaction.

  DOI：

  10.1021/jo2020906

文献信息

• 2,7-二甲氧基咔唑稠合化合物制备方法和应用
  申请人：沈阳药科大学

  公开号：CN113943300B

  公开（公告）日：2023-02-10

  本发明涉及2,7‑二甲氧基咔唑稠合化合物及其制备方法和应用，具体涉及化合物的合成方法和其作为荧光分子探针的应用，属于化学环境传感、以及生物技术领域。本发明提供了一系列2,7‑二甲氧基咔唑稠合化合物或其盐，其化学结构通式为：其中，R、R1‑R7如权利要求和说明书所述。本发明的化合物可以作为溶剂环境、温度敏感的化学传感器，也可以制备成识别特定DNA的荧光探针分子。
• A Green Fluorescent Nitrogen‐Doped Aromatic Belt Containing a [6]Cycloparaphenylene Skeleton
  作者：Fan Zhang、Xu‐Sheng Du、Da‐Wei Zhang、Yin‐Feng Wang、Hai‐Yan Lu、Chuan‐Feng Chen

  DOI：10.1002/anie.202104259

  日期：2021.7.5

  The design and synthesis of nitrogen-doped aromatic belts with conjugated structures still remain a challenge. Here, we report the first nitrogen-doped aromatic belt with a [6]cycloparaphenylene skeleton, which is conveniently synthesized from the easily available calix[3]carbazole. The aromatic belt has a rigid conjugated structure and deep cavity, and it can encapsulate one dichloromethane both in

  具有共轭结构的氮掺杂芳香带的设计和合成仍然是一个挑战。在这里，我们报告了第一个具有 [6] 环对亚苯基骨架的氮掺杂芳烃带，它是由容易获得的杯 [3] 咔唑方便地合成的。芳香带具有刚性共轭结构和深空腔，它可以在溶液和固态两种状态下包封一种二氯甲烷。有趣的是，芳香带显示出强的绿色荧光，量子产率为 0.39，并具有 2.02 eV 的窄 HOMO-LUMO 能隙。由三个咔唑亚基组成的带状共轭结构具有特定的光电特性，将促进在超分子化学和材料科学中的广泛应用。
• 一种杂原子桥连的荧光共轭芳香带及其制备方法与应用
  申请人：中国科学院化学研究所

  公开号：CN113149999B

  公开（公告）日：2022-09-13

  本发明公开了一种杂原子桥连的荧光共轭芳香带及其制备方法与应用。所述新型荧光共轭芳香带的结构式如式Ⅰ所示，式Ⅰ中，n表示重复单元的个数，为3～6之间的自然数；X为‑NAr、‑NR、O或S，其中，Ar表示苯基、取代苯基或苄基，R表示C1～C10的烷基。本发明提供的杂原子桥连的新型荧光共轭芳香带可作为模板或晶种生长结构均匀的单壁碳纳米管，其较大的空腔结构也可作为一种新型超分子主体材料，在有机半导体材料和超分子主客体化学等领域具有潜在的应用。本发明高效合成N原子桥连的新型荧光共轭芳香带的方法，原料廉价，合成方法简单，产物产率高。
• 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
• Liquid Triarylamines: The Scope and Limitations of Piers–Rubinsztajn Conditions for Obtaining Triarylamine–Siloxane Hybrid Materials
  作者：Brett A. Kamino、Bridget Mills、Christopher Reali、Michael J. Gretton、Michael A. Brook、Timothy P. Bender

  DOI：10.1021/jo2020906

  日期：2012.2.17

  New liquid triarylamine-siloxane hybrid materials are produced using the Piers-Rubinsztajn reaction. Under mild conditions, liquid analogues of conventional and commonly crystalline triarylamines are easily synthesized from readily available or accessible intermediates. Using a diverse selection of triarylamines, we explored the effects of siloxane group and substitution pattern on the physical properties of these materials, and we have demonstrated that relatively large molecular liquids with desirable electrochemical properties can be produced. The interactions between the strongly Lewis acidic catalyst used for this transformation, tris(pentafluorophenyl)borane (BCF), and the Lewis basic triarylamine substrates were studied. Through UV-vis-NIR and F-19 NMR spectroscopy, we have proposed that the catalyst undergoes a reversible redox reaction with the substrates to produce a charge transfer complex. The formation of this charge transfer complex is sensitive to the oxidation potential of the triarylamine and can greatly affect the kinetics of the Piers-Rubinsztajn reaction.