alpha-Methyl-alpha-hydroxy-gamma,gamma,gamma-trifluoro-4'-(methylthio)butyrophenone | 189956-22-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: alpha-Methyl-alpha-hydroxy-gamma,gamma,gamma-trifluoro-4'-(methylthio)butyrophenone
• 英文别名: 4,4,4-trifluoro-2-hydroxy-2-methyl-1-(4-methylsulfanylphenyl)butan-1-one
• CAS: 189956-22-7
• 化学式: C₁₂H₁₃F₃O₂S
• 分子量: 278.295
• InChiKey: IEUKCJLECPSQBT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  62.6
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  alpha-Methyl-alpha-hydroxy-gamma,gamma,gamma-trifluoro-4'-(methylthio)butyrophenone 在 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 生成 2-(R)-hydroxy-2-methyl-1-(4-(methylsulfonyl)phenyl)-4.4,4-trifluoro-1-butanone
  参考文献：
  名称：

  Discovery of a potent and selective COX-2 inhibitor in the alkoxy lactone series with optimized metabolic profile

  摘要：

  The COX-2 inhibitor DFP [5,5-dimethyl-3-(2-propoxy)-4-methanesulfonylphenyl)-2(5H)-furanone] was found to have a long half-life in humans. Analogues have been characterized in order to optimize pharmacokinetics. This has lead to the discovery of 5(S)-(5-ethyl-5-methyl-3-(2-propoxy)-4-methanesulfonylphenyl)-2(5H)-furanone analogue 11 a potent and selective COX-2 inhibitor which is metabolized to a greater extent than DFP upon incubation with rat and human hepatocytes, suggesting a shorter half-life in humans. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(02)00739-4
• 作为产物：
  描述：

  2-methyl-4,4,4-trifluorobutyryl chloride 在 三氯化铝 、 potassium tert-butylate 、 氧气 、 亚磷酸三乙酯 作用下， 以 四氢呋喃 、 氯仿 、 N,N-二甲基甲酰胺 为溶剂， 生成 alpha-Methyl-alpha-hydroxy-gamma,gamma,gamma-trifluoro-4'-(methylthio)butyrophenone
  参考文献：
  名称：

  Discovery of a potent and selective COX-2 inhibitor in the alkoxy lactone series with optimized metabolic profile

  摘要：

  The COX-2 inhibitor DFP [5,5-dimethyl-3-(2-propoxy)-4-methanesulfonylphenyl)-2(5H)-furanone] was found to have a long half-life in humans. Analogues have been characterized in order to optimize pharmacokinetics. This has lead to the discovery of 5(S)-(5-ethyl-5-methyl-3-(2-propoxy)-4-methanesulfonylphenyl)-2(5H)-furanone analogue 11 a potent and selective COX-2 inhibitor which is metabolized to a greater extent than DFP upon incubation with rat and human hepatocytes, suggesting a shorter half-life in humans. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(02)00739-4

文献信息

• US6057319A
  申请人：——

  公开号：US6057319A

  公开（公告）日：2000-05-02
• Discovery of a potent and selective COX-2 inhibitor in the alkoxy lactone series with optimized metabolic profile
  作者：Yves Leblanc、Patrick Roy、Zhaoyin Wang、Chun Sing Li、Nathalie Chauret、Deborah A. Nicoll-Griffith、José M. Silva、Yves Aubin、James A. Yergey、Chi Chung Chan、Denis Riendeau、Christine Brideau、Robert Gordon、Lijing Xu、Janine Webb、Denise M. Visco、Petpiboon Prasit

  DOI：10.1016/s0960-894x(02)00739-4

  日期：2002.11

  The COX-2 inhibitor DFP [5,5-dimethyl-3-(2-propoxy)-4-methanesulfonylphenyl)-2(5H)-furanone] was found to have a long half-life in humans. Analogues have been characterized in order to optimize pharmacokinetics. This has lead to the discovery of 5(S)-(5-ethyl-5-methyl-3-(2-propoxy)-4-methanesulfonylphenyl)-2(5H)-furanone analogue 11 a potent and selective COX-2 inhibitor which is metabolized to a greater extent than DFP upon incubation with rat and human hepatocytes, suggesting a shorter half-life in humans. (C) 2002 Elsevier Science Ltd. All rights reserved.