trifluoromethanesulfonic acid 5-methyl-2-phenyl-2H-pyrazol-3-yl ester | 276249-49-1

• 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-methyl-2-phenyl-2H-pyrazol-3-yl ester
• 英文别名: 3-Methyl-1-phenyl-5-trifluoromethylsulfonyloxypyrazole；3-methyl-1-phenyl-1H-pyrazol-5-yl trifluoromethanesulfonate；3-methyl-1-phenylpyrazol-5-yl trifluoromethanesulfonate；1-Phenyl-3-methyl-5-(trifluoromethylsulfonyloxy)-1H-pyrazole；(5-methyl-2-phenylpyrazol-3-yl) trifluoromethanesulfonate
• CAS: 276249-49-1
• 化学式: C₁₁H₉F₃N₂O₃S
• 分子量: 306.265
• InChiKey: DGPSBEXTTIRTOD-UHFFFAOYSA-N

物化性质

• 沸点：
  372.6±42.0 °C(Predicted)
• 密度：
  1.47±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 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-methyl-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84%的产率得到3-methyl-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：

  三氟甲磺酸酐 、 依达拉奉 在 2,4,6-三叔丁基吡啶 作用下， 以 1,2-二氯乙烷 为溶剂， 以94%的产率得到trifluoromethanesulfonic acid 5-methyl-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

• Pyrazolin-5-ylidene Palladium(II) Complexes: Synthesis, Characterization, and Application in the Direct Arylation of Pentafluorobenzene
  作者：Jan C. Bernhammer、Han Vinh Huynh

  DOI：10.1021/om300464b

  日期：2012.7.23

  Ten palladium(II) complexes bearing a pyrazolin-5-ylidene ligand have been synthesized by oxidative addition and silver carbene transfer pathways. The weakly bound acetonitrile ligand in the initially obtained trans-[PdBr2(MeCN)(Pyry)] complex (6, Pyry = 1-phenyl-2,3-dimethylpyrazolin-5-ylidene) could be replaced by other donor ligands, and additional NHC ligands were introduced either by silver carbene

  已经通过氧化加成和银卡宾转移途径合成了十个带有吡唑啉-5-亚烷基配体的钯（II）配合物。最初获得的反式-[PdBr 2（MeCN）（Pyry）]配合物（6，Pyry = 1-苯基-2,3-二甲基吡唑啉-5-亚烷基）中的弱结合乙腈配体可以被其他供体配体取代，并且通过卡宾银转移反应或通过与原位生成的游离卡宾的反应，可以引入其他NHC配体。使用我们先前报告的13基于13 C NMR的电子参数，吡唑啉5-亚烷基配体估计是迄今为止我们规模上最强的供体配体之一。在优化的条件下，将得到的配合物用作催化剂，以中等至良好的产率将五氟苯直接芳基化。
• Palladium-Catalyzed Coupling of Pyrazole Triflates with Arylboronic Acids
  作者：Curt A. Dvorak、Dale A. Rudolph、Sandy Ma、Nicholas I. Carruthers

  DOI：10.1021/jo0477897

  日期：2005.5.1

  A general protocol for the palladium-mediated Suzuki coupling reaction of pyrazole triflates and aryl boronic acids has been developed. The use of additional dppf ligand was determined to increase product yields allowing for the use of a broad range of reaction substrates.
• N-Fluoro-bis[(trifluoromethyl)sulfonyl]imide: interesting reactions involving nucleophilic attack on sulfonyl groups
  作者：Weiwen Ying、Darryl D. DesMarteau、Ze-Qi Xu、Michael Witz

  DOI：10.1016/s0022-1139(99)00231-6

  日期：2000.3

  N-Fluoro-bis[(trifluoromethyl)sulfonyl]imide (1) undergoes reaction with a variety of nucleophiles to give a number of interesting products. Under suitable conditions, the sulfonyl group on 1 is subject to nucleophilic attack forming N-fluoro-trifluoromethylsulfonyl amide (3) and Nu-SO2CF3. Surprisingly, 3 can also function as a weak nucleophile in the absence of other stronger bases. (C) 2000 Elsevier Science S.A. All rights reserved.