5,8,9-trimethyl-9H-carbazole-3-ol | 90135-57-2

• 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: 5,8,9-trimethyl-9H-carbazole-3-ol
• 英文别名: 5,8,9-Trimethyl-9H-carbazol-3-OL；5,8,9-trimethylcarbazol-3-ol
• CAS: 90135-57-2
• 化学式: C₁₅H₁₅NO
• 分子量: 225.29
• InChiKey: LNUYQBMTZPMXOM-UHFFFAOYSA-N

物化性质

• 熔点：
  202 °C(Solv: ethyl ether (60-29-7))
• 沸点：
  428.4±27.0 °C(Predicted)
• 密度：
  1.16±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  17
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  25.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  5,8,9-trimethyl-9H-carbazole-3-boronic acid 在 sodium hydroxide 、 双氧水 、 碳酸氢钠 作用下， 以 丙酮 为溶剂， 反应 24.0h， 以70%的产率得到5,8,9-trimethyl-9H-carbazole-3-ol
  参考文献：
  名称：

  Novel and efficient synthesis of 5,8-dimethyl-9H-carbazol-3-ol via a hydroxydeboronation reaction

  摘要：

  N-Protected carbazol-3-yl-boronic acid derivatives have been efficiently hydroxydeboronated under mild conditions by employing hydrogen peroxide. The method allows to easily obtain 3-hydroxycarbazoles as precursors of new analogs of the anticancer agent 9-hydroxyellipticine.

  DOI：

  10.1016/s0385-5414(07)81095-1

文献信息

• Antiproliferative activity of some 1,4-dimethylcarbazoles on cells that express estrogen receptors: part I
  作者：Anna Caruso、Adele Chimento、Hussein El-Kashef、Jean-Charles Lancelot、Antonella Panno、Vincenzo Pezzi、Carmela Saturnino、Maria Stefania Sinicropi、Rosa Sirianni、Sylvain Rault

  DOI：10.3109/14756366.2011.603132

  日期：2012.8.1

  Several 9H-carbazole derivatives are used for various pharmacological applications. Many of these compounds demonstrated cytotoxic and anticancer activities. In this work, we have investigated the cytotoxic activity of some substituted carbazoles against cancer cell lines (MCF-7, and ISK). The derivative 2a showed the highest inhibitory activity against both cell lines.
• Novel and efficient synthesis of 5,8-dimethyl-9H-carbazol-3-ol via a hydroxydeboronation reaction
  作者：A CARUSO、A VOISINCHIRET、J LANCELOT、M SINICROPI、A GAROFALO、S RAULT

  DOI：10.1016/s0385-5414(07)81095-1

  日期：2007.10.1

  N-Protected carbazol-3-yl-boronic acid derivatives have been efficiently hydroxydeboronated under mild conditions by employing hydrogen peroxide. The method allows to easily obtain 3-hydroxycarbazoles as precursors of new analogs of the anticancer agent 9-hydroxyellipticine.