4-(2-Nitroethyl)benzene-1,3-diol | 96853-42-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 4-(2-Nitroethyl)benzene-1,3-diol
• CAS: 96853-42-8
• 化学式: C₈H₉NO₄
• mdl: MFCD03410656
• 分子量: 183.164
• InChiKey: RRZCKBKLLPGVHT-UHFFFAOYSA-N

物化性质

• 熔点：
  75-76.5 °C
• 沸点：
  407.9±24.0 °C(Predicted)
• 密度：
  1.388±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  86.3
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-(2-Nitroethyl)benzene-1,3-diol 在 sodium methylate 、 silica gel 、 zinc(II) chloride 作用下， 反应 27.5h， 生成 补骨脂素
  参考文献：
  名称：

  一种高效全合成线性呋喃香豆素的新方法

  摘要：

  通过 Nef 反应和分子内环缩合在一个锅中合成线性呋喃香豆素的一种新方法导致苯并呋喃环的构建。该方法提供了一种轻松提供苯并呋喃骨架的新策略，并且还允许通过随后的 Pechmann 反应方便地合成香豆素环上具有不同取代基的呋喃香豆素衍生物。该策略也已应用于制备四种额外的苯并呋喃衍生物。

  DOI：

  10.1055/s-2006-926250
• 作为产物：
  描述：

  5-hydroxy-2-(2-nitroethenyl) phenol 在 sodium tetrahydroborate 作用下， 以 四氢呋喃 、 异丙醇 为溶剂， 反应 0.67h， 生成 4-(2-Nitroethyl)benzene-1,3-diol
  参考文献：
  名称：

  Structural modification of a specific antimicrobial lead against Helicobacter pylori discovered from traditional Chinese medicine and a structure–activity relationship study

  摘要：

  Psoralen (1a) was found to be a specific and potent antimicrobial lead against Helicobacter pylori (H. pylori) from a traditional Chinese medicine (TCM) in the bioassay directed isolation. A series of structurally diverse analogues of la were thus designed and synthesized to improve the antimicrobial potency, some of which showed more potent activities than the lead compound (1a) against H. pylori. Among them, compound 25a is 16-fold stronger (MIC = 0.39 mu g/mL) than 1a (MIC = 6.25 mu g/mL), and is even potent than the positive control metronidazole (MIC = 0.50 mu g/mL). The in vitro antimicrobial activities against H. pylori of these structurally diverse analogues based on the scaffold of la have also led to an outline of structure-activity relationship. (C) 2010 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2010.08.045

文献信息

• A Convenient Synthesis of 2-(2-Nitroethyl)-Phenols
  作者：Daniel Dauzonne、René Royer

  DOI：10.1055/s-1984-31078

  日期：——
• DAUZONNE, D.;ROYER, R., SYNTHESIS, BRD, 1984, N 12, 1054-1057
  作者：DAUZONNE, D.、ROYER, R.

  DOI：——

  日期：——
• Structural modification of a specific antimicrobial lead against Helicobacter pylori discovered from traditional Chinese medicine and a structure–activity relationship study
  作者：Bang-Le Zhang、Cheng-Qi Fan、Lei Dong、Fang-Dao Wang、Jian-Min Yue

  DOI：10.1016/j.ejmech.2010.08.045

  日期：2010.11

  Psoralen (1a) was found to be a specific and potent antimicrobial lead against Helicobacter pylori (H. pylori) from a traditional Chinese medicine (TCM) in the bioassay directed isolation. A series of structurally diverse analogues of la were thus designed and synthesized to improve the antimicrobial potency, some of which showed more potent activities than the lead compound (1a) against H. pylori. Among them, compound 25a is 16-fold stronger (MIC = 0.39 mu g/mL) than 1a (MIC = 6.25 mu g/mL), and is even potent than the positive control metronidazole (MIC = 0.50 mu g/mL). The in vitro antimicrobial activities against H. pylori of these structurally diverse analogues based on the scaffold of la have also led to an outline of structure-activity relationship. (C) 2010 Elsevier Masson SAS. All rights reserved.
• A New Efficient Method for the Total Synthesis of Linear Furocoumarins
  作者：Jian-Min Yue、Bang-Le Zhang、Fang-Dao Wang

  DOI：10.1055/s-2006-926250

  日期：——

  A new efficient method for the synthesis of linear furocoumarins by a Nef reaction and intramolecular cyclocondensation in one pot results in the construction of a benzofuran ring. This method provides a new strategy to furnish the benzofuran framework easily, and also allows the convenient synthesis of furocoumarin derivatives with different substituents on the coumarin ring by a subsequent Pechmann

  通过 Nef 反应和分子内环缩合在一个锅中合成线性呋喃香豆素的一种新方法导致苯并呋喃环的构建。该方法提供了一种轻松提供苯并呋喃骨架的新策略，并且还允许通过随后的 Pechmann 反应方便地合成香豆素环上具有不同取代基的呋喃香豆素衍生物。该策略也已应用于制备四种额外的苯并呋喃衍生物。