[2-(2-Hydroxymethyl-pyrrol-1-yl)-5-nitro-phenyl]-methanol | 854635-52-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: [2-(2-Hydroxymethyl-pyrrol-1-yl)-5-nitro-phenyl]-methanol
• 英文别名: [1-[2-(hydroxymethyl)-4-nitrophenyl]pyrrol-2-yl]methanol
• CAS: 854635-52-2
• 化学式: C₁₂H₁₂N₂O₄
• 分子量: 248.238
• InChiKey: ANYQEVBHIRXVLG-UHFFFAOYSA-N

物化性质

• 沸点：
  516.7±50.0 °C(Predicted)
• 密度：
  1.38±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.37
• 重原子数：
  18.0
• 可旋转键数：
  4.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  88.53
• 氢给体数：
  2.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  [2-(2-Hydroxymethyl-pyrrol-1-yl)-5-nitro-phenyl]-methanol 在 palladium on activated charcoal 盐酸 、 正丁基锂 、 sodium azide 、 ammonium formate 、 碳酸氢钠 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 正己烷 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 反应 2.67h， 生成 (R)-5-azidomethyl-3-(4H,6H-5-oxa-10b-azabenzo[e]azulen-8-yl)oxazolidin-2-one
  参考文献：
  名称：

  Substituent activity relationship studies on new azolo benzoxazepinyl oxazolidinones

  摘要：

  In an effort to discover potent antibacterials based on the entropically favored 'bioactive conformation' approach, a series of novel tricyclic molecules mimicking the conformationally constrained structure of Linezolid is reported. Based on the initial tricyclic molecule 1, the benzazepine derivative 2 was designed where the tricyclic structure had more flexibility around C-N bond compared to 1. While, the molecule 2 was less active, the molecule 3 showed promising antibacterial activity presumably after having obtained rigidity due to pyrrole ring. The syntheses, SAR studies, and evaluation of 3 as a lead compound are reported.

  DOI：

  10.1016/j.bmc.2006.07.040
• 作为产物：
  描述：

  5-硝基靛红酸酐 在 sodium hydroxide 、 sodium tetrahydroborate 、 溶剂黄146 、 三氯氧磷 作用下， 以 甲醇 为溶剂， 反应 4.75h， 生成 [2-(2-Hydroxymethyl-pyrrol-1-yl)-5-nitro-phenyl]-methanol
  参考文献：
  名称：

  Substituent activity relationship studies on new azolo benzoxazepinyl oxazolidinones

  摘要：

  In an effort to discover potent antibacterials based on the entropically favored 'bioactive conformation' approach, a series of novel tricyclic molecules mimicking the conformationally constrained structure of Linezolid is reported. Based on the initial tricyclic molecule 1, the benzazepine derivative 2 was designed where the tricyclic structure had more flexibility around C-N bond compared to 1. While, the molecule 2 was less active, the molecule 3 showed promising antibacterial activity presumably after having obtained rigidity due to pyrrole ring. The syntheses, SAR studies, and evaluation of 3 as a lead compound are reported.

  DOI：

  10.1016/j.bmc.2006.07.040

文献信息

• A synthetic route to a novel type of conformationally constrained N-aryloxazolidinones
  作者：Rosa Griera、Carme Cantos-Llopart、Mercedes Amat、Joan Bosch、Juan-C. del Castillo、Joan Huguet

  DOI：10.1016/j.bmcl.2005.03.071

  日期：2005.5

  The synthesis of N-aryloxazolidinone 1, a conformationally constrained analog of linezolid embodying a tricyclic pyrrolo[1,2-a][4,1]benzoxazepine moiety as the N-aryl substituent, is reported. The synthetic route involves the successive construction of the pyrrole, oxazepine, and oxazolidinone rings, with incorporation of the isoxazolylamino moiety in the last synthetic steps.

  报道了N-芳基恶唑烷酮1的合成，该构象受约束的利奈唑胺类似物，其表现为三环吡咯并[1,2-a] [4,1]苯并氮杂pine部分作为N-芳基取代基。合成途径包括依次构造吡咯，奥氮平和恶唑烷酮环，并在最后的合成步骤中引入异恶唑基氨基部分。