5-(4-tert-Butyl-phenoxy)-2-nitro-phenol | 42944-37-6

• 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: 5-(4-tert-Butyl-phenoxy)-2-nitro-phenol
• 英文别名: 5-(4-Tert-butylphenoxy)-2-nitrophenol
• CAS: 42944-37-6
• 化学式: C₁₆H₁₇NO₄
• 分子量: 287.315
• InChiKey: IZGMUOFIJXXINI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  75.3
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5-(4-tert-Butyl-phenoxy)-2-nitro-phenol 在 55 % Pd/C 、 氢气 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 15.0h， 以75%的产率得到2-amino-5-(4-tert-butylphenoxy)phenol
  参考文献：
  名称：

  6-Phenoxy-2-phenylbenzoxazoles, novel inhibitors of receptor for advanced glycation end products (RAGE)

  摘要：

  Receptor for advanced glycation end products (RAGE) is known to be involved in the transportation of amyloid beta (A beta) peptides and causes the accumulation of Ab in the brain. Moreover, recent studies suggest that the interactions between RAGE and Ab peptides may be the culprit behind Alzheimer's disease (AD). Inhibitors of the RAGE-A beta interactions would not only prevent the accumulation of toxic Ab in the brain, and but also block the progress of AD, therefore, have the potential to provide a 'disease-modifying therapy'. In this study, we have developed a series of 6-phenoxy-2-phenylbenzoxazole analogs as novel inhibitors of RAGE. Among these derivatives, we found several effective inhibitors that block the RAGE-Ab interactions without causing significant cellular toxicity. Further testing showed that compound 48 suppressed Ab induced toxicity in mouse hippocampal neuronal cells and reduced Ab levels in the brains of a-transgenic mouse model of AD after oral administration. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2015.05.022
• 作为产物：
  描述：

  4-叔丁基苯酚 、 2,4-二氟硝基苯 在 三氯化铁 、 lithium 、 氢化钾 作用下， 以 氨 、 水 为溶剂， 反应 4.83h， 生成 5-(4-tert-Butyl-phenoxy)-2-nitro-phenol 、 3-(4-tert-Butyl-phenoxy)-4-nitro-phenol
  参考文献：
  名称：

  亲核取代基对2,4-二氟硝基苯与苯氧化锂在液氨反应中取向的影响

  摘要：

  2,4-二氟硝基苯 (1) 芳氧基脱氟取向的依赖性 (o/p 比) 通过 X 取代的苯酚锂 2 (X = p-OMe, p-Me, p-Et, p-iPr , p-tBu, m-Me, H, pF) 在液氨中在 -55 到 -35 °C 的温度范围内进行了研究。邻氟取代的焓偏好随着取代基给电子能力的减弱而降低：p-OMe > p-Me ≈ p-Et > m-Me > H ⩾ pF。当 X = p-iPr 时，X = p-Me、p-Et 在邻位的主要氟取代变成了对位取代的偏好，并且这在 X = p-tBu 时进一步增加。PM3、AM1 和 MNDO MO 计算表明，在对位亲核试剂加成时形成的中间阴离子 σ-配合物具有更高的稳定性，因此表明 X = p-OMe、m-Me、H、pF 和 p-Alk = Me、Et 的主要邻位取代是由于基板中电荷分布对取向的控制。作为控制因素的底物电子结构可能会因中间阴离子

  DOI：

  10.1002/1099-0690(200101)2001:2<405::aid-ejoc405>3.0.co;2-6

文献信息

• 6-Phenoxy-2-phenylbenzoxazoles, novel inhibitors of receptor for advanced glycation end products (RAGE)
  作者：Kwanghyun Choi、Kwang Su Lim、Juhee Shin、Seo Hee Kim、Young-Ger Suh、Hyun-Seok Hong、Hee Kim、Hee-Jin Ha、Young-Ho Kim、Jiyoun Lee、Jeewoo Lee

  DOI：10.1016/j.bmc.2015.05.022

  日期：2015.8

  Receptor for advanced glycation end products (RAGE) is known to be involved in the transportation of amyloid beta (A beta) peptides and causes the accumulation of Ab in the brain. Moreover, recent studies suggest that the interactions between RAGE and Ab peptides may be the culprit behind Alzheimer's disease (AD). Inhibitors of the RAGE-A beta interactions would not only prevent the accumulation of toxic Ab in the brain, and but also block the progress of AD, therefore, have the potential to provide a 'disease-modifying therapy'. In this study, we have developed a series of 6-phenoxy-2-phenylbenzoxazole analogs as novel inhibitors of RAGE. Among these derivatives, we found several effective inhibitors that block the RAGE-Ab interactions without causing significant cellular toxicity. Further testing showed that compound 48 suppressed Ab induced toxicity in mouse hippocampal neuronal cells and reduced Ab levels in the brains of a-transgenic mouse model of AD after oral administration. (C) 2015 Elsevier Ltd. All rights reserved.
• The Influence of Nucleophile Substituents on the Orientation in the Reaction between 2,4-Difluoronitrobenzene and Lithium Phenoxides in Liquid Ammonia
  作者：Larisa Politanskaya、Evgenij Malykhin、Vitalij Shteingarts

  DOI：10.1002/1099-0690(200101)2001:2<405::aid-ejoc405>3.0.co;2-6

  日期：2001.1

  dependence of the orientation of aryloxydefluorination of 2,4-difluoronitrobenzene (1) (o/p ratio) by the action of X-substituted lithium phenoxides 2 (X = p-OMe, p-Me, p-Et, p-iPr, p-tBu, m-Me, H, p-F) in liquid ammonia in the temperature range from −55 to −35 °C has been investigated. The enthalpic preference for ortho-fluorine substitution decreases with weakening substituent electron-donating capability

  2,4-二氟硝基苯 (1) 芳氧基脱氟取向的依赖性 (o/p 比) 通过 X 取代的苯酚锂 2 (X = p-OMe, p-Me, p-Et, p-iPr , p-tBu, m-Me, H, pF) 在液氨中在 -55 到 -35 °C 的温度范围内进行了研究。邻氟取代的焓偏好随着取代基给电子能力的减弱而降低：p-OMe > p-Me ≈ p-Et > m-Me > H ⩾ pF。当 X = p-iPr 时，X = p-Me、p-Et 在邻位的主要氟取代变成了对位取代的偏好，并且这在 X = p-tBu 时进一步增加。PM3、AM1 和 MNDO MO 计算表明，在对位亲核试剂加成时形成的中间阴离子 σ-配合物具有更高的稳定性，因此表明 X = p-OMe、m-Me、H、pF 和 p-Alk = Me、Et 的主要邻位取代是由于基板中电荷分布对取向的控制。作为控制因素的底物电子结构可能会因中间阴离子