trifluoromethanesulfonic acid 5-tert-butyl-2-phenyl-2H-pyrazol-3-yl ester | 443912-79-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: trifluoromethanesulfonic acid 5-tert-butyl-2-phenyl-2H-pyrazol-3-yl ester
• 英文别名: 3-tert-butyl-1-phenyl-1H-pyrazol-5-yl trifluoromethanesulfonate；(5-Tert-butyl-2-phenylpyrazol-3-yl) trifluoromethanesulfonate
• CAS: 443912-79-6
• 化学式: C₁₄H₁₅F₃N₂O₃S
• 分子量: 348.346
• InChiKey: CIYNIAALWLGJTE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  69.6
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  trifluoromethanesulfonic acid 5-tert-butyl-2-phenyl-2H-pyrazol-3-yl ester 在 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 以87%的产率得到3-tert-butyl-1-phenyl-4-(trifluoromethylsulfonyl)-1H-pyrazol-5-ol
  参考文献：
  名称：

  Regioselective Synthesis of Heteroaryl Triflones by LDA (Lithium Diisopropylamide)-Mediated Anionic Thia-Fries Rearrangement

  摘要：

  Novel heteroaryl triflones including oxindole, pyrazolone, pyridine, and quinoline derivatives have been regioselectively synthesized by LDA-mediated thia-Fries rearrangement for the first time. These reactions are also the first examples of the application of anionic thia-Fries rearrangement in heteroaromatic compounds.

  DOI：

  10.1021/ol300842d
• 作为产物：
  描述：

  新戊酰基乙酸甲酯 在 2,4,6-三叔丁基吡啶 、 溶剂黄146 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 1.0h， 生成 trifluoromethanesulfonic acid 5-tert-butyl-2-phenyl-2H-pyrazol-3-yl ester
  参考文献：
  名称：

  Regioselective Synthesis of Heteroaryl Triflones by LDA (Lithium Diisopropylamide)-Mediated Anionic Thia-Fries Rearrangement

  摘要：

  Novel heteroaryl triflones including oxindole, pyrazolone, pyridine, and quinoline derivatives have been regioselectively synthesized by LDA-mediated thia-Fries rearrangement for the first time. These reactions are also the first examples of the application of anionic thia-Fries rearrangement in heteroaromatic compounds.

  DOI：

  10.1021/ol300842d

文献信息

• Pyrazole Urea-Based Inhibitors of p38 MAP Kinase:  From Lead Compound to Clinical Candidate
  作者：John Regan、Steffen Breitfelder、Pier Cirillo、Thomas Gilmore、Anne G. Graham、Eugene Hickey、Bernhard Klaus、Jeffrey Madwed、Monica Moriak、Neil Moss、Chris Pargellis、Sue Pav、Alfred Proto、Alan Swinamer、Liang Tong、Carol Torcellini

  DOI：10.1021/jm020057r

  日期：2002.7.1

  We report on a series of N-pyrazole, N'-aryl ureas and their mode of binding to p38 mitogen activated protein kinase. Importantly, a key binding domain that is distinct from the adenosine 5'-triphoshate (ATP) binding site is exposed when the conserved activation loop, consisting in part of Asp168-Phe169-Gly170, adopts a conformation permitting lipophilic and hydrogen bonding interactions between this class of inhibitors and the protein. We describe the correlation of the structure-activity relationships and crystallographic structures of these inhibitors with p38. In addition, we incorporated another binding pharmacophore that forms a hydrogen bond at the ATP binding site. This modification affords significant improvements in binding, cellular, and in vivo potencies resulting in the selection of 45 (BIRB 796) as a clinical candidate for the treatment of inflammatory diseases.