pyrazolone d₅ | 1228765-67-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑啉类
• 英文名称: pyrazolone d₅
• 英文别名: 1-(d5-phenyl)-3-methyl-1H-pyrazol-5(4H)-one；Edaravone D5；5-methyl-2-(2,3,4,5,6-pentadeuteriophenyl)-4H-pyrazol-3-one
• CAS: 1228765-67-0
• 化学式: C₁₀H₁₀N₂O
• 分子量: 179.162
• InChiKey: QELUYTUMUWHWMC-VIQYUKPQSA-N

物化性质

• 溶解度：
  可溶于氯仿（少许）、DMSO（少许）、甲醇（少许）

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  32.7
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  pyrazolone d₅ 、 1-[(三异丙基硅烷基)乙炔基]-1,2-苯碘酰-3(1H)-酮 在 silver hexafluoroantimonate 、 dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer 、 sodium carbonate 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 0.17h， 生成 3-methyl-1-(2-((triisopropylsilyl)ethynyl)phenyl)-1H-pyrazol-5(4H)-one
  参考文献：
  名称：

  金（i）和铑（iii）催化的1-芳基吡唑酮的正式区域发散性C–H炔基化†

  摘要：

  通过使用高价碘试剂作为炔烃源，在Rh（III）和Au（I）配合物的催化下，实现了1-芳基-5-吡唑啉酮的形式区域发散C–H烷基化。机理研究表明，区域选择性不仅归因于催化剂的选择，还归因于底物的性质。底物范围和官能团的相容性已经过全面检查。

  DOI：

  10.1039/c8ob00585k
• 作为产物：
  描述：

  氘代苯 在 盐酸 、 硫酸 、 氢气 、 硝酸 、 sodium acetate 、 10% Pd/C 、 溶剂黄146 、 sodium nitrite 作用下， 以 甲醇 、 水 为溶剂， 110.0 ℃ 、101.33 kPa 条件下， 反应 16.0h， 生成 pyrazolone d₅
  参考文献：
  名称：

  钯催化吡唑-3-酮与取代联烯酸酯的[4 + 2]环化平行合成吡唑酮稠合肉啉

  摘要：

  开发了通过钯催化的 C-H 活化/环化级联从吡唑-3-酮和 α,γ-取代联烯酸酯合成吡唑酮稠合肉桂啉的方法。机理研究揭示了反应过程。最初， N-酰基-缬氨酸配体辅助的邻位-C-H活化得到邻位-烯基化中间体。随后的环钯化和联烯酸的迁移插入产生七元钯环。还原消除最终得到吡唑啉酮稠合的肉啉。

  DOI：

  10.1021/acs.joc.3c02165

文献信息

• Rh(III)-Catalyzed (4 + 1) Annulation of Pyrazol-3-ones with Alkynoates via <i>Ortho</i>-Alkenylation/Cyclization Cascade: Synthesis of Indazole-Fused Pyrazoles
  作者：Wei-Jung Chiu、Hong-Ren Chen、Indrajeet J. Barve、Chung-Ming Sun

  DOI：10.1021/acs.joc.2c01208

  日期：2022.9.16

  A facile synthesis of novel indazole-fused pyrazoles from pyrazol-3-ones and alkynoate esters/amides via Rh(III)-catalyzed sequential C–H activation/ortho-alkenylation/intramolecular cyclization cascade is reported. The important characteristic of this method is that the resulting scaffold bearing quaternary carbon has been obtained through unusual [4 + 1] rather than expected [4 + 2] addition where

  报道了通过 Rh(III) 催化的顺序 C-H 活化/邻位-烯基化/分子内环化级联从 pyrazol-3-ones 和炔酸酯/酰胺轻松合成新型吲唑稠合吡唑。该方法的重要特征是所得的带有季碳的支架是通过不寻常的 [4 + 1] 而不是预期的 [4 + 2] 添加获得的，其中炔酸盐充当单碳单元。
• Ru(II)-Catalyzed and Ligand-Controlled C–H Activation and Annulation via 1,2-Phenyl Shift: Synthesis of Quaternary Carbon-Centered Pyrimidoindolones
  作者：Swagata Baruah、Pallabi Saikia、Gauri Duarah、Sanjib Gogoi

  DOI：10.1021/acs.orglett.8b01330

  日期：2018.7.6

  A novel Ru(II)-catalyzed C-H activation and annulation reaction of N-arylpyrazol-5-ones and diaryl/arylalkyl-substituted alkynes is developed. Unlike the reported metal-catalyzed C-H activation and annulation reactions, in the present bidentate amine-ligand controlled C-H activation and annulation reaction, the annulation occurs via a 1,2-aryl shift to afford quaternary carbon-centered pyrimidoindolones.
• Relative quantitation of glycans using stable isotopic labels 1-(d0/d5) phenyl-3-methyl-5-pyrazolone by mass spectrometry
  作者：Ping Zhang、Ying Zhang、Xiangdong Xue、Chenjian Wang、Zhongfu Wang、Linjuan Huang

  DOI：10.1016/j.ab.2011.07.006

  日期：2011.11

  A deuterium reagent, 1-(d5) phenyl-3-methyl-5-pyrazolone (d5-PMP), has been synthesized and used for relative quantitative analysis of oligosaccharides by mass spectrometry (MS) using d0/d5-PMP stable isotopic labeling. Previously reported permethylation-based isotopic labels generate variable mass differences, and reductive amination-based isotopic labels cause a loss of some acid-labile groups in carbohydrates. In contrast, d0/d5-PMP stable isotopic labeling is performed at the reducing end of glycans under basic conditions without desialylation, and the mass difference (Delta m = 10 Da) between the heavy form (d5-PMP derivative) and light form (d0-PMP derivative) of each glycan is invariable. When the two derivative forms of a glycan are mixed in equimolar amounts, a pair of peaks with a 10-Da mass differences is observed in the MS profile. The difference at relative intensity between the d0- and d5-PMP derivatives reflects the difference in quantity of glycans in two samples, making it possible to carry out both qualitative and relative quantitative analyses of glycans in glycomic studies. Application of this method on DP(2) to DP(6) maltodextrin oligosaccharides and N-linked glycans released from ribonuclease B and bovine fetuin demonstrates a 10-fold relative quantitative dynamic range, a satisfying reproducibility (coefficient of variation [CV] <= 8.34%), and good accuracy (relative error [RE] <= 5.1%) of the method. The suggested technique has been successfully applied for comparative quantitative analysis of free oligosaccharides in human and bovine milk. (C) 2011 Elsevier Inc. All rights reserved.
• PYRAZOLINONE SCAVENGERS OF FREE RADICAL
  申请人：Gant Thomas G.

  公开号：US20100150899A1

  公开（公告）日：2010-06-17

  The present invention relates to new pyrazolinone scavengers of free radicals, pharmaceutical compositions thereof, and methods of use thereof.