1-(2,4-二羟基-3-丙基苯基)-2,2,2-三氟乙酮 | 65239-69-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 1-(2,4-二羟基-3-丙基苯基)-2,2,2-三氟乙酮
• 英文名称: 2,4-dihydroxy-3-propyl-1',1',1'-trifluoroacetophenone
• 英文别名: 2,4-dihydroxy-3-propyltrifluoroacetophenone；1-(2,4-Dihydroxy-3-propylphenyl)-2,2,2-trifluoroethanone
• CAS: 65239-69-2
• 化学式: C₁₁H₁₁F₃O₃
• 分子量: 248.202
• InChiKey: FNUWZRSFCFUFFU-UHFFFAOYSA-N

物化性质

• 熔点：
  114°C
• 沸点：
  341.2±37.0 °C(Predicted)
• 密度：
  1.352±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  57.5
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  1-(2,4-二羟基-3-丙基苯基)-2,2,2-三氟乙酮 在 硫酸 、 potassium carbonate 作用下， 以 四氢呋喃 、 水 、 丙酮 为溶剂， 反应 43.5h， 生成 4-{[4-(trifluoroacetyl)-3-hydroxy-2-propylphenoxy]methyl}benzoic acid
  参考文献：
  名称：

  Hydroxyacetophenone-derived antagonists of the peptidoleukotrienes

  摘要：

  Considerations of the possible similarities between leukotriene D4 and its prototypical antagonist, FPL 55712, led to the development of a new series of leukotriene antagonists incorporating a hydroxyacetophenone group (e.g., the toluic acids 16 and 18). Although considerable attention has focused on FPL 55712-derived analogues, only limited investigations into alternatives for the standard 4-acetyl-3-hydroxy-2-propylphenoxy moiety have been reported. Therefore, an extensive study of modifications to the hydroxyacetophenone portion of toluic acid 18 was undertaken. Although no viable alternative to the 3-hydroxy moiety was discovered, replacements for the 2-propyl group (34, 37) and the 4-acetyl functionality (56, 59) yielded potent antagonists. A number of compounds exhibited longer duration of action in vivo than FPL 55712.

  DOI：

  10.1021/jm00124a014
• 作为产物：
  描述：

  1-(2,4-二羟基苯基)-2,2,2-三氟乙酮 在 palladium on activated charcoal 氢气 、 caesium carbonate 作用下， 以 N,N-二甲基甲酰胺 、 邻二氯苯 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 生成 1-(2,4-二羟基-3-丙基苯基)-2,2,2-三氟乙酮
  参考文献：
  名称：

  Phenylacetic acid derivatives as hPPAR agonists

  摘要：

  Beginning with the weakly active lead structure 1, a new series of WAR agonists was developed. In vivo glucose and triglyceride lowering activity was obtained by homologation and oxamination to 3, then conversion to substituted benzisoxazoles 4 and 5. Further manipulation afforded benzofurans 6 and 7. Compound 7 was of comparable potency as a glucose and triglyceride lowering agent in insulin resistant rodents to BRL 49653. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(03)00115-x

文献信息

• Therapeutic compounds for treating dyslipidemic conditions
  申请人：Huang Y. Shaei

  公开号：US20050113419A1

  公开（公告）日：2005-05-26

  The present invention relates to novel LXR ligands of Formula I and the pharmaceutically acceptable salts, esters and tautomers thereof, which are useful in the treatment of dyslipidemic conditions, particularly depressed levels of HDL cholesterol.

  本发明涉及公式I的新型LXR配体及其药用盐、酯和互变异构体，可用于治疗脂质代谢异常症，特别是降低HDL胆固醇水平。
• [EN] THERAPEUTIC COMPOUNDS FOR TREATING DYSLIPIDEMIC CONDITIONS<br/>[FR] COMPOSES THERAPEUTIQUES DESTINES AU TRAITEMENT D'ETATS DYSLIPIDEMIQUES
  申请人：MERCK & CO INC

  公开号：WO2004011448A1

  公开（公告）日：2004-02-05

  The present invention relates to novel LXR ligands of Formula I and the pharmaceutically acceptable salts, esters and tautomers thereof, which are useful in the treatment of dyslipidemic conditions, particularly depressed levels of HDL cholesterol.

  本发明涉及式I的新LXR配体及其药用可接受的盐、酯和互变异构体，它们在治疗血脂异常状况，特别是低HDL胆固醇水平方面具有用途。
• BE853558
  申请人：——

  公开号：——

  公开（公告）日：——
• WO2007/81335
  申请人：——

  公开号：——

  公开（公告）日：——
• Discovery of a Novel Series of Peroxisome Proliferator-Activated Receptor α/γ Dual Agonists for the Treatment of Type 2 Diabetes and Dyslipidemia
  作者：Kun Liu、Libo Xu、Joel P. Berger、Karen L. MacNaul、Gauchao Zhou、Thomas W. Doebber、Michael J. Forrest、David E. Moller、A. Brian Jones

  DOI：10.1021/jm048993p

  日期：2005.4.1

  A series of 2-aryloxy-2-methyl-propionic acid compounds and related analogues were designed, synthesized, and evaluated for their PPAR agonist activities. 2-[(5,7-Dipropyl-3-trifluoromethyl)-benzisoxazol-6-yloxy]-2-methylpropionic acid (4) was identified as a PPAR alpha/gamma dual agonist with relative PPAR alpha selectivity and demonstrated potent efficacy in lowering both glucose and lipids in animal models without causing body weight gain. The PPAR alpha activity of 4 appeared to have played a significant role in lowering glucose levels in db/db mice.