2-phenanthridinylmethanol | 40737-03-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 2-phenanthridinylmethanol
• 英文别名: 6-(hydroxymethyl)phenanthridine；Phenanthridin-6-ylmethanol
• CAS: 40737-03-9
• 化学式: C₁₄H₁₁NO
• 分子量: 209.247
• InChiKey: DENRVIVSMQDNEO-UHFFFAOYSA-N

物化性质

• 沸点：
  415.9±20.0 °C(Predicted)
• 密度：
  1.270±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  33.1
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  phenanthridine-6-carboxylic acid 在 氯化亚砜 、 lithium tri-t-butoxyaluminum hydride 作用下， 以 四氢呋喃 为溶剂， 反应 11.0h， 生成 2-phenanthridinylmethanol
  参考文献：
  名称：

  Syntheses of 9-acridine- and 2-phenanthridinemethanols as potential antimalarials

  摘要：

  alpha-(1-Piperidinylmethyl)-9-acridinemethanol (3), alpha-[(dibutylamino)ethyl]-9-acridanmethanol (4a), and alpha-[(dibutylamino)methyl]-2-phenanthridinemethanol (5) have been made and all are ineffective as antimalarials against Plasmodium berghei in mice. 9-Acridinyloxirane showed no significant mutagenicity for strains TA 98 or TA 100 of Salmonella typhimurium.

  DOI：

  10.1021/jm00140a022

文献信息

• Hydroxymethylation of Quinolines with Na₂ S₂ O₈ by a Radical Pathway
  作者：Luan Zhou、Naoki Okugawa、Hideo Togo

  DOI：10.1002/ejoc.201701321

  日期：2017.11.9

  Treatment of quinolines bearing methyl, fluoro, chloro, bromo, acetyl, methoxycarbonyl, trifluoromethyl, or cyano groups with Na2S2O8 in a mixture of methanol and water at 70 °C for 4 h gave the corresponding hydroxymethylated compounds in good to moderate yields. The hydroxymethyl group of the product was transformed into aldehyde, ester, amide, aminomethyl, cyano, and tetrazole groups.

  在甲醇和水的混合物中，用Na 2 S 2 O 8在70°C下处理带有甲基，氟，氯，溴，乙酰基，甲氧基羰基，三氟甲基或氰基的喹啉4小时，得到相应的羟甲基化化合物中等产量。产物的羟甲基被转化为醛，酯，酰胺，氨甲基，氰基和四唑基。
• Visible light-induced hydroxymethylation and formylation of (iso)quinolines with alcohols
  作者：Yilan Zhang、Xiaoguang Yue、Jiashun Zhu、Jiehai Peng、Chenxin Zhou、Jirong Wu、Pengfei Zhang

  DOI：10.1016/j.mcat.2022.112594

  日期：2022.9

  Herein, a mild and effective hydroxymethylation and formylation of quinolines or isoquinolines with methanol in the absence of external acids and transition metals is described using the coupling reaction promoted by PhIFA and visible light. A variety of substituted quinolines or isoquinolines proceed the reaction smoothly, providing the corresponding products in moderate-to-good yields. Control experiments

  在此，使用由 PhIFA 和可见光促进的偶联反应，描述了在没有外部酸和过渡金属的情况下，喹啉或异喹啉与甲醇的温和有效的羟甲基化和甲酰化。多种取代的喹啉或异喹啉使反应顺利进行，以中等至良好的收率提供相应的产物。对照实验表明，这种转变涉及一种激进的途径。
• Syntheses of 9-acridine- and 2-phenanthridinemethanols as potential antimalarials
  作者：Chester W. Muth、Howard L. Minigh、Suchart Chookruvong、Larry A. Hall、Hung-Tai Chao

  DOI：10.1021/jm00140a022

  日期：1981.8

  alpha-(1-Piperidinylmethyl)-9-acridinemethanol (3), alpha-[(dibutylamino)ethyl]-9-acridanmethanol (4a), and alpha-[(dibutylamino)methyl]-2-phenanthridinemethanol (5) have been made and all are ineffective as antimalarials against Plasmodium berghei in mice. 9-Acridinyloxirane showed no significant mutagenicity for strains TA 98 or TA 100 of Salmonella typhimurium.