4-(tetrahydrofurfuryloxy)nitrobenzene | 91134-13-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 4-(tetrahydrofurfuryloxy)nitrobenzene
• 英文别名: Furan, tetrahydro-2-[(4-nitrophenoxy)methyl]-；2-[(4-nitrophenoxy)methyl]oxolane
• CAS: 91134-13-3
• 化学式: C₁₁H₁₃NO₄
• 分子量: 223.229
• InChiKey: JXIKEKBKCOHIHX-UHFFFAOYSA-N

物化性质

• 熔点：
  51-52 °C
• 沸点：
  192-195 °C(Press: 5 Torr)
• 密度：
  1.232±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  64.3
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-(tetrahydrofurfuryloxy)nitrobenzene 在 铁粉 、 氯化铵 作用下， 以 甲醇 、 水 为溶剂， 反应 2.0h， 生成 4-(四氢-呋喃-2-甲氧基)-苯胺
  参考文献：
  名称：

  Structural optimization of diphenylpyrimidine derivatives (DPPYs) as potent Bruton's tyrosine kinase (BTK) inhibitors with improved activity toward B leukemia cell lines

  摘要：

  A new series of diphenylpyrimidine derivatives (DPPYs) bearing various aniline side chains at the C-2 position of pyrimidine core were synthesized as potent BTK inhibitors. Most of these inhibitors displayed improved activity against B leukemia cell lines compared with lead compound spebrutinib. Subsequent studies showed that the peculiar inhibitor 7j, with IC50 values of 10.5 AM against Ramos cells and 19.1 AM against Raji cells, also displayed slightly higher inhibitory ability than the novel agent ibrutinib. Moreover, compound 7j is not sensitive to normal cells PBMC, indicating low cell cytotoxicity. In addition, flow cytometry analysis indicated that 7j significantly induced the apoptosis of Ramos cells, and arrested the cell cycle at the GO/G1 phase. These explorations provided new clues to discover pyrimidine scaffold as more effective BTK inhibitors. 2017 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2016.11.047
• 作为产物：
  描述：

  四氢糠醇 、 对氟硝基苯 在 potassium carbonate 作用下， 以 乙腈 为溶剂， 反应 12.0h， 生成 4-(tetrahydrofurfuryloxy)nitrobenzene
  参考文献：
  名称：

  Structural optimization of diphenylpyrimidine derivatives (DPPYs) as potent Bruton's tyrosine kinase (BTK) inhibitors with improved activity toward B leukemia cell lines

  摘要：

  A new series of diphenylpyrimidine derivatives (DPPYs) bearing various aniline side chains at the C-2 position of pyrimidine core were synthesized as potent BTK inhibitors. Most of these inhibitors displayed improved activity against B leukemia cell lines compared with lead compound spebrutinib. Subsequent studies showed that the peculiar inhibitor 7j, with IC50 values of 10.5 AM against Ramos cells and 19.1 AM against Raji cells, also displayed slightly higher inhibitory ability than the novel agent ibrutinib. Moreover, compound 7j is not sensitive to normal cells PBMC, indicating low cell cytotoxicity. In addition, flow cytometry analysis indicated that 7j significantly induced the apoptosis of Ramos cells, and arrested the cell cycle at the GO/G1 phase. These explorations provided new clues to discover pyrimidine scaffold as more effective BTK inhibitors. 2017 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2016.11.047

文献信息

• Organosoluble Copper Clusters as Precatalysts for Carbon−Heteroelement Bond-Forming Reactions:  Microwave and Conventional Heating
  作者：Gerald F. Manbeck、Adam J. Lipman、Robert A. Stockland,、Adrienne L. Freidl、Amy F. Hasler、Joshua J. Stone、Ilia A. Guzei

  DOI：10.1021/jo048761y

  日期：2005.1.1

  The coupling of aryl iodides with alcohols under mild conditions has been explored using self-assembled octanuclear copper clusters as catalysts. Reactions involving tetrahydrofurfuryl alcohol were typically complete in 4−8 h at 110 °C using an oil bath or 1−3 h with microwave heating. High yields of alkyl aryl ethers were obtained with catalyst loadings as low as 0.4 mol % cluster.

  使用自组装的八核铜簇作为催化剂，探索了在温和条件下芳基碘化物与醇的偶联。涉及四氢糠醇的反应通常在110°C的油浴中4-8小时内完成，或在微波加热下1-3小时内完成。以低至0.4mol％簇的催化剂负载量获得了高产率的烷基芳基醚。
• US4857070A
  申请人：——

  公开号：US4857070A

  公开（公告）日：1989-08-15