2-benzyl-5-methyl-1H-pyrazol-3-one | 946-24-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-benzyl-5-methyl-1H-pyrazol-3-one
• 英文别名: 1-benzyl-5-hydroxy-3-methyl-1H-pyrazole；1-benzyl-3-methyl-1H-pyrazol-5-ol；1-Benzyl-3-methyl-5-hydroxy-pyrazol
• CAS: 946-24-7
• 化学式: C₁₁H₁₂N₂O
• mdl: MFCD03964563
• 分子量: 188.229
• InChiKey: FQSMUDOPPUNPDW-UHFFFAOYSA-N

物化性质

• 沸点：
  366.3±30.0 °C(Predicted)
• 密度：
  1.14±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.04
• 重原子数：
  14.0
• 可旋转键数：
  2.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.181
• 拓扑面积：
  38.05
• 氢给体数：
  1.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  2-benzyl-5-methyl-1H-pyrazol-3-one 在 calcium hydroxide 、 硫酸 作用下， 以 1,4-二氧六环 为溶剂， 反应 26.0h， 生成 1-benzyl-3-methyl-6-phenyl-5,6-dihydro-1H-pyrano[2,3-c]pyrazol-4-one
  参考文献：
  名称：

  New 1-Substituted 4-Cinnamoyl-5- hydroxypyrazoles and Precursors thereof: Synthesis, Ring Closure Reactions and NMR-Spectroscopic Investigations

  摘要：

  Reaction of 1-substituted 5-hydroxy-1H-pyrazoles (pyrazolones) with trans-cinnamoyl chloride/calcium hydroxide in dioxane affords the corresponding 4-cinnamoyl-5-hydroxy-1H-pyrazoles. Cyclization of the latter into 5,6-dihydropyrano[2,3-c]pyrazol-4-ones proceeds in very low yields upon treatment with concentrated sulfuric acid. 1,6-Diphenyl-1H-pyrano[2,3-c]pyrazol-4-one was synthesized by reaction of of 4-acetyl-5-hydroxy-1-phenyl-1H-pyrazole with benzoyl chloride and lithium bis(trimethylsilyl)amide and subsequent cyclization of the thus obtained 1,3-diketone. NMR-spectroscopic investigations with the obtained 4-substituted 5-hydroxypyrazoles and their precursors regarding their tautomeric behavior in various solvents are presented.

  DOI：

  10.3987/com-03-9857
• 作为产物：
  描述：

  乙酰乙酸乙酯 、 苄基肼 以 溶剂黄146 为溶剂， 生成 2-benzyl-5-methyl-1H-pyrazol-3-one
  参考文献：
  名称：

  Structure–activity relationship and improved hydrolytic stability of pyrazole derivatives that are allosteric inhibitors of West Nile Virus NS2B-NS3 proteinase

  摘要：

  West Nile Virus (WNV) is a potentially deadly mosquito-borne flavivirus which has spread rapidly throughout the world. Currently there is no effective vaccine against flaviviral infections. We previously reported the identification of pyrazole ester derivatives as allosteric inhibitors of WNV NS2B-NS3 proteinase. These compounds degrade rapidly in pH 8 buffer with a half life of 1-2 h. We now report the design, synthesis and in vitro evaluation of pyrazole derivatives that are inhibitors of WNV NS2B-NS3 proteinase with greatly improved stability in the assay medium. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.07.150

文献信息

• Direct and Chemoselective Electrophilic Monofluoromethylation of Heteroatoms (<i>O</i>-, <i>S-</i>, <i>N</i>-, <i>P</i>-, <i>Se</i>-) with Fluoroiodomethane
  作者：Raffaele Senatore、Monika Malik、Markus Spreitzer、Wolfgang Holzer、Vittorio Pace

  DOI：10.1021/acs.orglett.9b04654

  日期：2020.2.21

  The commercially available fluoroiodomethane represents a valuable and effective electrophilic source for transferring the CH2F unit to a series of heteroatom-centered nucleophiles under mild basic conditions. The excellent manipulability offered by its liquid physical state (bp 53.4 °C) enables practical and straightforward one-step nucleophilic substitutions to retain the chiral information embodied

  市售的氟碘甲烷代表了一种有价值的有效的亲电子来源，用于在温和的碱性条件下将CH2F单元转移到一系列以杂原子为中心的亲核试剂上。它的液态物理状态（bp 53.4°C）提供了出色的可操作性，可进行实用且直接的一步亲核取代，以保留所体现的手性信息，从而使其实际上克服了对氟甲基化剂的需求，而无需立即使用。高产率方法已成功应用于各种亲核试剂，包括当前市场上的一系列药物。
• Iodine-catalyzed sulfenylation of pyrazolones using dimethyl sulfoxide as an oxidant
  作者：Yogesh Siddaraju、Kandikere Ramaiah Prabhu

  DOI：10.1039/c7ob00561j

  日期：——

  An iodine catalyzed sulfenylation of pyrazolones with a diverse range of heterocyclic thiols, heterocyclic thiones and disulfides has been described using dimethyl sulfoxide as an oxidant, which is an inexpensive, readily available and green oxidant. The present methodology exhibits a wide range of substrate scope and targeted products were obtained in good to excellent yields under metal-free conditions

  使用二甲亚砜作为氧化剂已经描述了碘催化吡唑酮与各种范围的杂环硫醇，杂环硫酮和二硫化物的亚磺酰基化，该二甲亚砜是便宜的，容易获得的绿色氧化剂。本方法学展示了广泛的底物范围，并且在短时间内在无金属条件下以良好至优异的产率获得了目标产物。这种方法为吡唑啉酮的硫醚化提供了一个简单的形成C–S键的方法。
• COMPOSITIONS AND METHODS FOR INHIBITION OF THE JAK PATHWAY
  申请人：Li Hui

  公开号：US20080306099A1

  公开（公告）日：2008-12-11

  The invention encompasses compounds having formula I-V and the compositions and methods using these compounds in the treatment of conditions in which modulation of the JAK pathway or inhibition of JAK kinases, particularly JAK3, may be therapeutically useful.

  该发明涵盖具有I-V式的化合物以及使用这些化合物治疗调节JAK通路或抑制JAK激酶，特别是JAK3在治疗可能有治疗作用的疾病中的组合物和方法。
• Diastereoselective Synthesis of Indolindiones by Formal [5+1] Double Michael Cycloaddition to 4-Cinnamoylpyrrolediones
  作者：Pavel S. Silaichev、Valeriy O. Filimonov、Pavel A. Slepukhin、Michael Rubin、Andrey N. Maslivets

  DOI：10.1002/ejoc.201500141

  日期：2015.4

  An efficient [5+1] double Michael cycloaddition of enolates to 4-cinnamoylpyrrole-2,3-diones was investigated; the reaction allows for the highly diastereoselective assembly of indoline scaffolds with up to three contiguous stereogenic centers.

  研究了烯醇化物与 4-肉桂酰吡咯-2,3-二酮的有效 [5+1] 双迈克尔环加成反应；该反应允许具有多达三个连续立体中心的二氢吲哚支架的高度非对映选择性组装。
• Keratin Dyeing Compositions Comprising a Radical Scavenger and a Chelant and Use Thereof
  申请人：Zhang Guiru

  公开号：US20110035886A1

  公开（公告）日：2011-02-17

  The invention relates to colorant compositions for the oxidative dyeing of keratin fibers comprising an inhibiting system of radical scavengers and chelants in the dyeing composition. The invention also relates to methods for reducing color formation outside of the keratin fiber during oxidative dyeing comprising using such colorant compositions.