3,6-di-tert-butyl-9-(oxiran-2-ylmethyl)-9H-carbazole | 1505522-27-9

• 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-di-tert-butyl-9-(oxiran-2-ylmethyl)-9H-carbazole
• CAS: 1505522-27-9
• 化学式: C₂₃H₂₉NO
• 分子量: 335.489
• InChiKey: FDEIIOZFCVCZDD-UHFFFAOYSA-N

物化性质

• 沸点：
  476.4±27.0 °C(predicted)
• 密度：
  1.07±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.79
• 重原子数：
  25.0
• 可旋转键数：
  2.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  17.46
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  3,6-di-tert-butyl-9-(oxiran-2-ylmethyl)-9H-carbazole 在 三聚氯氰 、 硫氰酸铵 作用下， 以 四氢呋喃 为溶剂， 反应 12.0h， 以70%的产率得到3,6-di-tert-butyl-9-(thiiran-2-ylmethyl)-9H-carbazole
  参考文献：
  名称：

  咔唑基聚合物作为蓝色铱发射体的基质：合成，光物理和高效PLED

  摘要：

  本文报道了新的咔唑基聚合物的合成及其在基质中的应用，该溶液以溶液处理的发光层掺杂有环金属化的Ir（III）配合物，在天蓝色聚合物发光器件（PLED）中发挥作用。我们系统地研究了它们对PLED性能的影响。用这些聚合物实现了19.7cd A -1的电流效率和1850 cd m -2的亮度。研究表明，PLED中电致磷光量子效率的下降主要源于具有叔丁基的主体中掺杂剂之间的三重态-三重态an灭。已经证明，在主机没有叔的设备中丁基基团的效率下降也受到电场淬灭的影响。在这些基于咔唑的聚合物中，形成了三联体二聚体，叔丁基不限制分子间的相互作用以防止三联体二聚体的形成，尽管如此，叔丁基仍会降低电荷传输。

  DOI：

  10.1039/c3tc31441c
• 作为产物：
  描述：

  咔唑 在 aluminum (III) chloride 、 potassium carbonate 、 potassium hydroxide 作用下， 以 二氯甲烷 、 丁酮 为溶剂， 反应 1.0h， 生成 3,6-di-tert-butyl-9-(oxiran-2-ylmethyl)-9H-carbazole
  参考文献：
  名称：

  咔唑基聚合物作为蓝色铱发射体的基质：合成，光物理和高效PLED

  摘要：

  本文报道了新的咔唑基聚合物的合成及其在基质中的应用，该溶液以溶液处理的发光层掺杂有环金属化的Ir（III）配合物，在天蓝色聚合物发光器件（PLED）中发挥作用。我们系统地研究了它们对PLED性能的影响。用这些聚合物实现了19.7cd A -1的电流效率和1850 cd m -2的亮度。研究表明，PLED中电致磷光量子效率的下降主要源于具有叔丁基的主体中掺杂剂之间的三重态-三重态an灭。已经证明，在主机没有叔的设备中丁基基团的效率下降也受到电场淬灭的影响。在这些基于咔唑的聚合物中，形成了三联体二聚体，叔丁基不限制分子间的相互作用以防止三联体二聚体的形成，尽管如此，叔丁基仍会降低电荷传输。

  DOI：

  10.1039/c3tc31441c

文献信息

• Potential Antimicrobial Isopropanol-Conjugated Carbazole Azoles as Dual Targeting Inhibitors of <i>Enterococcus faecalis</i>
  作者：Yuan Zhang、Vijai Kumar Reddy Tangadanchu、Yu Cheng、Ren-Guo Yang、Jian-Mei Lin、Cheng-He Zhou

  DOI：10.1021/acsmedchemlett.7b00514

  日期：2018.3.8

  A series of isopropanol-bridged carbazole azoles as potential antimicrobial agents were designed and synthesized from commercial carbazoles. Bioassay revealed that 3,6-dichlorocarbazolyl triazole 3f could effectively inhibit the growth of E. faecalis with minimal inhibitory concentration of 2 mu g/mL. The active molecule 3f showed lower propensity to trigger the development of resistance in bacteria than norfloxacin and exerted rapidly bactericidal ability. Compound 3f also exhibited low cytotoxicity to normal mammalian RAW264.7 cells. Further mechanism exploration indicated that conjugate 3f was membrane active against E. faecalis and could form 3f-DNA complex by intercalating into DNA of resistant E. faecalis, which might be responsible for its antimicrobial action. Molecular docking showed an efficient binding of triazole derivative 3f with DNA gyrase enzyme through noncovalent interactions.
• Identification of Racemic and Chiral Carbazole Derivatives Containing an Isopropanolamine Linker as Prospective Surrogates against Plant Pathogenic Bacteria: <i>In Vitro</i> and <i>In Vivo</i> Assays and Quantitative Proteomics
  作者：Yong-Liang Zhao、Xing Huang、Li-Wei Liu、Pei-Yi Wang、Qing-Su Long、Qing-Qing Tao、Zhong Li、Song Yang

  DOI：10.1021/acs.jafc.9b02036

  日期：2019.7.3

  Recent observations on the emergence of drug-resistant plant pathogenic bacteria have highlighted and elicited an acute campaign to develop novel, highly efficient antibiotic surrogates for managing bacterial diseases in agriculture. Thus, a type of racemic and chiral carbazole derivative containing an isopropanolamine pattern was systematically synthesized to discover low-cost and efficient antibacterial candidates. Screening results showed that compounds 2f, 6c, and 2j could significantly suppress the growth of tested plant pathogens, namely Xanthomonas oryzae pv oryzae, X. axonopodis pv citri, and Pseudomonas syringae pv actinidiae, and provided the corresponding EC50 values of 1.27, 0.993, and 0.603 mu g/mL, which were significantly better than those of existing commercial drugs. In vivo studies confirmed their prospective applications for controlling plant bacterial diseases. Label-free quantitative proteomics analysis indicated that compound 2f could dramatically induce the up- and down-regulation of a total of 247 differentially expressed proteins, which was further validated by the parallel reaction monitoring technique. Moreover, fluorescence spectra and SEM images were obtained to further explore the antibacterial mechanism.