3-叔丁基-4-硝基苯酚 | 5722-68-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 中文名称: 3-叔丁基-4-硝基苯酚
• 英文名称: 4-Nitro-3-tert-butylphenol
• 英文别名: 3-tert-Butyl-4-nitrophenol
• CAS: 5722-68-9
• 化学式: C₁₀H₁₃NO₃
• mdl: MFCD09965931
• 分子量: 195.218
• InChiKey: MVPHMJZSIXHKOP-UHFFFAOYSA-N

物化性质

• 沸点：
  141 °C(Press: 1 Torr)
• 密度：
  1.173±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  66
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-叔丁基-4-硝基苯酚 在 四氯化碳 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 1.5h， 生成 3-(tert-butyl)-4-nitrophenyl dihydrogen phosphate
  参考文献：
  名称：

  Utilization of Nitrophenylphosphates and Oxime-Based Ligation for the Development of Nanomolar Affinity Inhibitors of the Yersinia pestis Outer Protein H (YopH) Phosphatase

  摘要：

  Our current study reports the first K(M) optimization of a library of nitrophenylphosphate-containing substrates for generating an inhibitor lead against the Yersinia pestis outer protein phosphatase (YopH). A high activity substrate identified by this method (K(M) = 80 mu M) was converted from a subs trate into an inhibitor by replacement of its phosphate group with difluoromethylphosphonic acid, and by attachment of an aminooxy handle for further structural optimization by mime ligation. A cocrystal structure of this aminooxy-containing platform in complex with YopH allowed the identification of a conserved water molecule proximal to the aminooxy group that was subsequenly employed for the design of furanyl-based oxime derivatives. By this process, a potent (IC(50) = 190 nM) and nonpromiscuous inhibitor was developed with good YopH selectivity relative to a panel of phosphatases. The inhibitor showed significant inhibition Of intracellular Y pestis replication at a noncytotoxic concentration. The current work presents general approaches to PTP inhibitor development that may be useful beyond YopH.

  DOI：

  10.1021/jm200022g
• 作为产物：
  描述：

  3-叔丁基苯酚 在 硝酸 、 溶剂黄146 作用下， 生成 3-叔丁基-4-硝基苯酚
  参考文献：
  名称：

  Doepp,D.; Brugger,E., Liebigs Annalen der Chemie, 1979, p. 554 - 563

  摘要：

  DOI：

文献信息

• Studies on the two-phase nitration of selected phenols
  作者：Malcolm J. Thompson、Petrus J. Zeegers

  DOI：10.1016/s0040-4039(00)87910-1

  日期：1988.1

  The two phase nitration of several phenols by aqueous acid, sodium nitrate and diethyl ether, yielded as well as the expected nitro-phenols, a benzoquinone. A variable induction period was observed which could be significantly reduced by added sodium nitrite.

  用酸水溶液，硝酸钠和乙醚对几种酚进行两相硝化，得到了预期的硝基酚苯甲醌。观察到可变的诱导期，可以通过添加亚硝酸钠显着减少诱导期。
• DOEPP D.; BRUGGER E., LIEBIGS ANN. CHEM., 1979, NO 4, 554-563
  作者：DOEPP D.、 BRUGGER E.

  DOI：——

  日期：——
• Doepp,D.; Brugger,E., Liebigs Annalen der Chemie, 1979, p. 554 - 563
  作者：Doepp,D.、Brugger,E.

  DOI：——

  日期：——
• Utilization of Nitrophenylphosphates and Oxime-Based Ligation for the Development of Nanomolar Affinity Inhibitors of the <i>Yersinia pestis</i> Outer Protein H (YopH) Phosphatase
  作者：Medhanit Bahta、George T. Lountos、Beverly Dyas、Sung-Eun Kim、Robert G. Ulrich、David S. Waugh、Terrence R. Burke

  DOI：10.1021/jm200022g

  日期：2011.4.28

  Our current study reports the first K(M) optimization of a library of nitrophenylphosphate-containing substrates for generating an inhibitor lead against the Yersinia pestis outer protein phosphatase (YopH). A high activity substrate identified by this method (K(M) = 80 mu M) was converted from a subs trate into an inhibitor by replacement of its phosphate group with difluoromethylphosphonic acid, and by attachment of an aminooxy handle for further structural optimization by mime ligation. A cocrystal structure of this aminooxy-containing platform in complex with YopH allowed the identification of a conserved water molecule proximal to the aminooxy group that was subsequenly employed for the design of furanyl-based oxime derivatives. By this process, a potent (IC(50) = 190 nM) and nonpromiscuous inhibitor was developed with good YopH selectivity relative to a panel of phosphatases. The inhibitor showed significant inhibition Of intracellular Y pestis replication at a noncytotoxic concentration. The current work presents general approaches to PTP inhibitor development that may be useful beyond YopH.