9-(2-(oxiran-2-yl)ethyl)-9H-carbazole | 141410-65-3

• 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: 9-(2-(oxiran-2-yl)ethyl)-9H-carbazole
• CAS: 141410-65-3
• 化学式: C₁₆H₁₅NO
• 分子量: 237.301
• InChiKey: KYTCCWTWXTZVPP-UHFFFAOYSA-N

物化性质

• 沸点：
  420.4±27.0 °C(predicted)
• 密度：
  1.22±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.22
• 重原子数：
  18.0
• 可旋转键数：
  3.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  17.46
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  9-(2-(oxiran-2-yl)ethyl)-9H-carbazole 、 2-萘硫醇 在 水 作用下， 以 乙醇 为溶剂， 反应 16.0h， 以69%的产率得到4-(9H-carbazol-9-yl)-1-(naphthalen-2-ylthio)butan-2-ol
  参考文献：
  名称：

  Synthesis and structure–activity relationship studies of 1,3-disubstituted 2-propanols as BACE-1 inhibitors

  摘要：

  A library of 1,3-disubstituted 2-propanols was synthesized and evaluated as low molecular weight probes for beta-secretase inhibition. By screening a library of 121 1,3-disubstituted 2-propanol derivatives, we identified few compounds inhibiting the enzyme at low micromolar concentrations. The initial hits were optimized to yield a potent BACE-1 inhibitor exhibiting an IC50 constant in the nanomolar range. Exploration of the pharmacological properties revealed that these small molecular inhibitors possessed a high selectivity over cathepsin D and desirable physicochemical properties beneficial to cross the blood-brain barrier. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.05.072
• 作为产物：
  描述：

  9-(but-3-en-1-yl)-9H-carbazole 在 potassium hydrogencarbonate 、 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 反应 16.0h， 以22.6%的产率得到9-(2-(oxiran-2-yl)ethyl)-9H-carbazole
  参考文献：
  名称：

  Synthesis and structure–activity relationship studies of 1,3-disubstituted 2-propanols as BACE-1 inhibitors

  摘要：

  A library of 1,3-disubstituted 2-propanols was synthesized and evaluated as low molecular weight probes for beta-secretase inhibition. By screening a library of 121 1,3-disubstituted 2-propanol derivatives, we identified few compounds inhibiting the enzyme at low micromolar concentrations. The initial hits were optimized to yield a potent BACE-1 inhibitor exhibiting an IC50 constant in the nanomolar range. Exploration of the pharmacological properties revealed that these small molecular inhibitors possessed a high selectivity over cathepsin D and desirable physicochemical properties beneficial to cross the blood-brain barrier. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.05.072

文献信息

• Solution-processed blue phosphorescent OLEDs with carbazole-based polymeric host materials
  作者：Frédéric Dumur、Layla Beouch、Sebastien Peralta、Guillaume Wantz、Fabrice Goubard、Didier Gigmes

  DOI：10.1016/j.orgel.2015.06.013

  日期：2015.10

  A new carbazole-based polymer PEPEK varying from the previously reported PEPK by the length of the spacer between the polymer backbone and the pendent carbazole moiety was investigated as polymeric host for solution-processed devices. Interestingly, if the two polymers are structurally close since the length of the alkyl chain only differs from one carbon atom, the previously reported PEPK gave higher performances than the newly synthesized PEPEK when tested as host for the wide bandgap triplet emitter FIrpic. To optimize electroluminescence performances, two device configurations were examined. On doping the emissive layer of phosphorescent organic light-emitting devices (OLEDs) at 16 wt% with FIrpic, best PEPK-based OLEDs gave an efficacy of 15.14 cd/A whereas PEPEK-based devices furnished an efficiency of 12.17 cd/A in the same conditions. To determine the origin of this unexpected behavior, the new polymer PEPEK was characterized by UV-visible absorption and luminescence spectroscopy as well as cyclic voltammetry. Thermal properties of PEPEK were also examined and compared to those of PEPK. (C) 2015 Elsevier B.V. All rights reserved.