4,4-二氟-5-甲基-2-苯基吡唑-3-酮 | 56875-01-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑啉类
• 中文名称: 4,4-二氟-5-甲基-2-苯基吡唑-3-酮
• 英文名称: 4,4-difluoro-5-methyl-2-phenyl-2,4-dihydro-3H-pyrazol-3-one
• 英文别名: 4,4-Difluoro-3-methyl-1-phenyl-2-pyrazolin-5-one；4,4-difluoro-5-methyl-2-phenyl-2,4-dihydro-pyrazol-3-one；3H-Pyrazol-3-one, 4,4-difluoro-2,4-dihydro-5-methyl-2-phenyl-；4,4-difluoro-5-methyl-2-phenylpyrazol-3-one
• CAS: 56875-01-5
• 化学式: C₁₀H₈F₂N₂O
• 分子量: 210.183
• InChiKey: DBPNTHKZUSEJDV-UHFFFAOYSA-N

物化性质

• 沸点：
  286.9±40.0 °C(Predicted)
• 密度：
  1.31±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  15
• 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：
  4

反应信息

• 作为产物：
  描述：

  安替比林 在 N-fluorobis<(trifluoromethyl)sulfonyl>imide 作用下， 以 氯仿 为溶剂， 反应 120.0h， 以38%的产率得到4,4-二氟-5-甲基-2-苯基吡唑-3-酮
  参考文献：
  名称：

  N-Fluoro-bis[(trifluoromethyl)sulfonyl]imide: interesting reactions involving nucleophilic attack on sulfonyl groups

  摘要：

  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.

  DOI：

  10.1016/s0022-1139(99)00231-6

文献信息

• One-pot multistep mechanochemical synthesis of fluorinated pyrazolones
  作者：Joseph L Howard、William Nicholson、Yerbol Sagatov、Duncan L Browne

  DOI：10.3762/bjoc.13.189

  日期：——

  Solventless mechanochemical synthesis represents a technique with improved sustainability metrics compared to solvent-based processes. Herein, we describe a methodical process to run one solventless reaction directly into another through multistep mechanochemistry, effectively amplifying the solvent savings. The approach has to consider the solid form of the materials and compatibility of any auxiliary used. This has culminated in the development of a two-step, one-jar protocol for heterocycle formation and subsequent fluorination that has been successfully applied across a range of substrates, resulting in 12 difluorinated pyrazolones in moderate to excellent yields.

  无溶剂机械化合成代表一种与基于溶剂的工艺相比具有改进的可持续性指标的技术。在这里，我们描述了一种系统化的方法，通过多步机械化学直接将一个无溶剂反应转化为另一个，有效地增加了溶剂节约。这种方法需要考虑材料的固态形式以及任何辅助剂的兼容性。这已经发展成为一种两步一瓶的协议，用于杂环化合物的形成和随后的氟化反应，已成功应用于一系列底物，产率在中等到优良之间，共得到了12种二氟吡唑酮。
• Selective, Electrophilic Fluorinations Using N-Fluoro-o-benzenedisulfonimide
  作者：Franklin A. Davis、Wei Han、Christopher K. Murphy

  DOI：10.1021/jo00120a014

  日期：1995.7

  The synthesis of N-fluoro-o-benzenedisulfonimide (NFOBS, 2) and its use as an ''electrophilic'' fluorinating reagent with nucleophilic substrates is described and compared with that of N-fluorobenzenesulfonimide (NFSi, 3). NFOBS (2) is prepared in three steps in 81% overall yield from commercially available o-benzenedisulfonic acid (4) and involves treatment of o-benzenedisulfonimide (6) with dilute fluorine (10% F-2/N-2). Reaction of 2 with metal enolates, silyl enol ethers, and 1,3-dicarbonyl compounds affords the corresponding alpha-fluoro compounds in yields up to 95%, with good control of mono- and difluorination. Fluorination of ortho-metalated aromatic compounds was achieved in modest to good yields (10-80%). While the reactivities of 2 and 3 are similar, better yields were observed with the former reagent in the fluorination of metal enolates, Grignard and lithium reagents, while 3 gave better results with the ortho-lithiated aromatic substrates. The available evidence suggests an S(N)2-type mechanism for the fluorination of nucleophilic substrates by these reagents.
• SHIUE C.-Y.; WOLF A. P., J. LABELLED COMPOUNDS AND RADIOPHARM., 1981, 18, NO 7, 1059-1066
  作者：SHIUE C.-Y.、 WOLF A. P.

  DOI：——

  日期：——
• US4436717A
  申请人：——

  公开号：US4436717A

  公开（公告）日：1984-03-13
• 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.