5-fluoro-2-((4-(trifluoromethyl)benzyl)oxy)benzaldehyde | 946134-86-7

• 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-fluoro-2-((4-(trifluoromethyl)benzyl)oxy)benzaldehyde
• 英文别名: 5-Fluoro-2-[[4-(trifluoromethyl)phenyl]methoxy]benzaldehyde；5-fluoro-2-[[4-(trifluoromethyl)phenyl]methoxy]benzaldehyde
• CAS: 946134-86-7
• 化学式: C₁₅H₁₀F₄O₂
• 分子量: 298.237
• InChiKey: ALXXZMWCWGNREY-UHFFFAOYSA-N

物化性质

• 熔点：
  50-52 °C
• 沸点：
  373.4±37.0 °C(predicted)
• 密度：
  1.334±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  5-fluoro-2-((4-(trifluoromethyl)benzyl)oxy)benzaldehyde 在 lithium hydroxide 、 lithium aluminium tetrahydride 、 caesium carbonate 、 甲基磺酰氯 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 乙腈 为溶剂， 生成 2-(7-(2-(4-(trifluoromethyl)benzyloxy)-5-fluorobenzylthio)-2,3-dihydro-1H-inden-4-yloxy)acetic acid
  参考文献：
  名称：

  Discovery of highly potent and selective benzyloxybenzyl-based peroxisome proliferator-activator receptor (PPAR) δ agonists

  摘要：

  A series of 1,4-benzyloxybenzylsulfanylaryl carboxylic acids were prepared and their activities for PPAR receptor subtypes (alpha, beta, and gamma) with potential indications for the treatment of dyslipidemia were investigated. Analog 13a displayed the greatest binding affinity (IC50 = 10 nM) and selectivity (120-fold) for PPAR delta over PPAR alpha. Many of the analogs investigated were found to be highly selective for PPAR delta and were dependent on the point of attachment of the substituent. In the 1,4-series, analog 28e was found to be the most potent (IC50 = 1.7 nM) and selective (> 1000-fold) compound for PPAR delta. None of the compounds tested showed appreciable binding affinity for PPAR gamma. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2007.04.046
• 作为产物：
  描述：

  5-氟水杨醛 、 1-溴-三氟对二甲苯 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以98%的产率得到5-fluoro-2-((4-(trifluoromethyl)benzyl)oxy)benzaldehyde
  参考文献：
  名称：

  Thiazolidinedione derivatives as PTP1B inhibitors with antihyperglycemic and antiobesity effects

  摘要：

  Benzylidene-2,4-thiazolidinedione derivatives with substitutions on the phenyl ring at the ortho or para positions of the thiazolidinedione (TZD) group were synthesized as PTP1B inhibitors with IC50 values in a low micromolar range. Compound 3e, the lowest, bore an IC50 of 5.0 mu M. In vivo efficacy of 3e as an antiobesity and hypoglycemic agent was evaluated in a mouse model system. Significant improvement of glucose tolerance was observed. This compound also significantly suppressed weight gain and significantly improved blood parameters such as TG, total cholesterol and NEFA. Compound 3e was also found to activate peroxisome proliferator-activated receptors (PPARs) indicating multiple mechanisms of action. (c) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.09.020

文献信息

• Discovery of highly potent and selective benzyloxybenzyl-based peroxisome proliferator-activator receptor (PPAR) δ agonists
  作者：Larry D. Bratton、Gary F. Filzen、Andrew Geyer、Jennifer K. Hoffman、Gina Lu、Jim Pulaski、Bharat K. Trivedi、Paul C. Unangst、Xiangyang Xu

  DOI：10.1016/j.bmcl.2007.04.046

  日期：2007.7

  A series of 1,4-benzyloxybenzylsulfanylaryl carboxylic acids were prepared and their activities for PPAR receptor subtypes (alpha, beta, and gamma) with potential indications for the treatment of dyslipidemia were investigated. Analog 13a displayed the greatest binding affinity (IC50 = 10 nM) and selectivity (120-fold) for PPAR delta over PPAR alpha. Many of the analogs investigated were found to be highly selective for PPAR delta and were dependent on the point of attachment of the substituent. In the 1,4-series, analog 28e was found to be the most potent (IC50 = 1.7 nM) and selective (> 1000-fold) compound for PPAR delta. None of the compounds tested showed appreciable binding affinity for PPAR gamma. (c) 2007 Elsevier Ltd. All rights reserved.
• Thiazolidinedione derivatives as PTP1B inhibitors with antihyperglycemic and antiobesity effects
  作者：Bharat Raj Bhattarai、Bhooshan Kafle、Ji-Sun Hwang、Deegendra Khadka、Sun-Myung Lee、Jae-Seung Kang、Seung Wook Ham、Inn-Oc Han、Hwangseo Park、Hyeongjin Cho

  DOI：10.1016/j.bmcl.2009.09.020

  日期：2009.11

  Benzylidene-2,4-thiazolidinedione derivatives with substitutions on the phenyl ring at the ortho or para positions of the thiazolidinedione (TZD) group were synthesized as PTP1B inhibitors with IC50 values in a low micromolar range. Compound 3e, the lowest, bore an IC50 of 5.0 mu M. In vivo efficacy of 3e as an antiobesity and hypoglycemic agent was evaluated in a mouse model system. Significant improvement of glucose tolerance was observed. This compound also significantly suppressed weight gain and significantly improved blood parameters such as TG, total cholesterol and NEFA. Compound 3e was also found to activate peroxisome proliferator-activated receptors (PPARs) indicating multiple mechanisms of action. (c) 2009 Elsevier Ltd. All rights reserved.