4,4,4-三氟-1-(苯并-[b]-噻吩)丁烷-1,3-二酮 | 392-29-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻吩类
• 中文名称: 4,4,4-三氟-1-(苯并-[b]-噻吩)丁烷-1,3-二酮
• 英文名称: 1-(3-benzo{b}thienyl)-4,4,4-trifluoro-1,3-butanedione
• 英文别名: 3-(4,4,4-trifluoro-1,3-dioxobutyl)benzothiophene；1-benzo[b]thiophen-3-yl-4,4,4-trifluoro-butane-1,3-dione；1-Benzo[b]thiophen-3-yl-4,4,4-trifluor-butan-1,3-dion；3-Thianaphthenoyltrifluoroacetone；1-(1-benzothiophen-3-yl)-4,4,4-trifluorobutane-1,3-dione
• CAS: 392-29-0
• 化学式: C₁₂H₇F₃O₂S
• 分子量: 272.248
• InChiKey: NFWFGKBSGANQQK-UHFFFAOYSA-N

物化性质

• 熔点：
  40 °C
• 沸点：
  351.0±37.0 °C(Predicted)
• 密度：
  1.424±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  62.4
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  4,4,4-三氟-1-(苯并-[b]-噻吩)丁烷-1,3-二酮 、 4-磺酰胺基苯肼盐酸盐 以 乙醇 为溶剂， 反应 20.0h， 生成 4-(5-Benzo[b]thiophen-3-yl-3-trifluoromethyl-pyrazol-1-yl)-benzenesulfonamide
  参考文献：
  名称：

  Synthesis and Biological Evaluation of the 1,5-Diarylpyrazole Class of Cyclooxygenase-2 Inhibitors:  Identification of 4-[5-(4-Methylphenyl)-3- (trifluoromethyl)-1H-pyrazol-1-yl]benzenesulfonamide (SC-58635, Celecoxib)

  摘要：

  A series of sulfonamide-containing 1,5-diarylpyrazole derivatives were prepared and evaluated for their ability to block cyclooxygenase-2 (COX-2) in vitro and in vivo. Extensive structure-activity relationship (SAR) work was carried out within this series, and a number of potent and selective inhibitors of COX-2 were identified. Since an early structural lead (1f, SC-236) exhibited an unacceptably long plasma half-life, a number of pyrazole analogs containing potential metabolic sites were evaluated further in vivo in an effort to identify compounds with acceptable pharmacokinetic profiles. This work led to the identification of ii (4-[5-(4-methylphenyl)-3-(trifluoromethyl)-1H-pyrazol-1-yl]benzenesulfonamide, SC-58635, celecoxib), which is currently in phase III clinical trials for the treatment of rheumatoid arthritis and osteoarthritis.

  DOI：

  10.1021/jm960803q
• 作为产物：
  描述：

  3-乙酰硫茚 在 乙醚 、 三氟乙酸乙酯 、 sodium methylate 作用下， 生成 4,4,4-三氟-1-(苯并-[b]-噻吩)丁烷-1,3-二酮
  参考文献：
  名称：

  The Synthesis of Certain Beta-Diketones Containing Perfluoromethyl and Perfluoro-n-propyl Groups

  摘要：

  DOI：

  10.1021/ja01154a037

文献信息

• Synthesis and luminescence-spectral properties of benzoheterocyclic β-diketones and their complexes with europium
  作者：T. S. Kostryukova、N. P. Ivanovskaya、A. I. Lyamin、D. V. Romanov、N. S. Osin、G. V. Zatonsky、N. V. Vasil’ev

  DOI：10.1134/s1070363212030152

  日期：2012.3

  In order to solve some environmental and biomedical problems, we synthesized fluorinated heterocyclic beta-diketones and estimated the luminescence-spectral properties of these compounds complexes with the ions of rare-earth elements as the possible reagents for immunofluorescence analysis.
• Gmelin Handbuch der Anorganischen Chemie, Gmelin Handbook: Sc: MVol.D3, 5.1.22.2, page 235 - 235
  作者：

  DOI：——

  日期：——
• Veel, A. E.; Gerard, J., Microchimica Acta
  作者：Veel, A. E.、Gerard, J.

  DOI：——

  日期：——
• Synthesis and Biological Evaluation of the 1,5-Diarylpyrazole Class of Cyclooxygenase-2 Inhibitors:  Identification of 4-[5-(4-Methylphenyl)-3- (trifluoromethyl)-1<i>H</i>-pyrazol-1-yl]benzenesulfonamide (SC-58635, Celecoxib)
  作者：Thomas D. Penning、John J. Talley、Stephen R. Bertenshaw、Jeffery S. Carter、Paul W. Collins、Stephen Docter、Matthew J. Graneto、Len F. Lee、James W. Malecha、Julie M. Miyashiro、Roland S. Rogers、D. J. Rogier、Stella S. Yu、Gary D. Anderson、Earl G. Burton、J. Nita Cogburn、Susan A. Gregory、Carol M. Koboldt、William E. Perkins、Karen Seibert、Amy W. Veenhuizen、Yan Y. Zhang、Peter C. Isakson

  DOI：10.1021/jm960803q

  日期：1997.4.1

  A series of sulfonamide-containing 1,5-diarylpyrazole derivatives were prepared and evaluated for their ability to block cyclooxygenase-2 (COX-2) in vitro and in vivo. Extensive structure-activity relationship (SAR) work was carried out within this series, and a number of potent and selective inhibitors of COX-2 were identified. Since an early structural lead (1f, SC-236) exhibited an unacceptably long plasma half-life, a number of pyrazole analogs containing potential metabolic sites were evaluated further in vivo in an effort to identify compounds with acceptable pharmacokinetic profiles. This work led to the identification of ii (4-[5-(4-methylphenyl)-3-(trifluoromethyl)-1H-pyrazol-1-yl]benzenesulfonamide, SC-58635, celecoxib), which is currently in phase III clinical trials for the treatment of rheumatoid arthritis and osteoarthritis.
• The Synthesis of Certain Beta-Diketones Containing Perfluoromethyl and Perfluoro-n-propyl Groups
  作者：Lloyd B. Barkley、Robert Levine

  DOI：10.1021/ja01154a037

  日期：1951.10