5-methyl-2-(3-methylphenyl)-2,4-dihydropyrazol-3-one | 20124-80-5

• 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: 5-methyl-2-(3-methylphenyl)-2,4-dihydropyrazol-3-one
• 英文别名: 5-methyl-2-(m-tolyl)-2,4-dihydropyrazol-3-one；3-methyl-1-(m-tolyl)-1H-pyrazol-5(4H)-one；5-methyl-2-(m-tolyl)-2,4-dihydropyrazole-3-one；1-(3-Methylphenyl)-3-methylpyrazolon-5；5-methyl-2-m-tolyl-1,2-dihydro-pyrazol-3-one；3-methyl-1-(3'-methylphenyl)-2-pyrazolin-5-one；3-methyl-1-(3-methylphenyl)-3-pyrazolin-5-one；5-methyl-2-(3-methylphenyl)-2,4-dihydro-3H-pyrazol-3-one；5-methyl-2-(3-methylphenyl)-4H-pyrazol-3-one
• CAS: 20124-80-5
• 化学式: C₁₁H₁₂N₂O
• mdl: MFCD03167125
• 分子量: 188.229
• InChiKey: GWHZXIMAQAFUCP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.272
• 拓扑面积：
  32.7
• 氢给体数：
  0
• 氢受体数：
  2

安全信息

• 海关编码：
  2933199090

反应信息

• 作为反应物：
  描述：

  5-methyl-2-(3-methylphenyl)-2,4-dihydropyrazol-3-one 在 potassium carbonate 、 三氯氧磷 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成
  参考文献：
  名称：

  Synthesis and in vitro antimicrobial screening of new pyrano[4,3-b]pyrane derivatives of 1H-pyrazole

  摘要：

  A new series of pyrano[4,3-b]pyrane 4a-1 bearing 1H-pyrazole has been synthesized by one pot base catalyzed cyclocondensation reaction of 1H-pyrazole-4-carbaldehyde 1a-1, malononitrile 2 and 4-hydroxy-6-methylpyrone 3. All the synthesized compounds were screened against six bacterial pathogens, namely B. subtilis, C. tetani, S. pneutnoniae, S. typhi, V cholerae, E. coli and antifungal activity against, two fungal pathogens, A. fumigatus and C. albicans using broth microdilution MIC method. Some of the compounds are found to be equipotent or more potent than that of commercial drugs, against most of employed strains. (C) 2011 Chetan B. Sangani. Published by Elsevier B.V. on behalf of Chinese Chemical Society. All rights reserved.

  DOI：

  10.1016/j.cclet.2011.09.012
• 作为产物：
  描述：

  3-氯甲苯 在 bis[chloro(1,2,3-trihapto-allylbenzene)palladium(II)] 、 N-[2-二(1-金刚烷)磷苯基]吗啉 、 一水合肼 、 溶剂黄146 、 sodium t-butanolate 作用下， 以 甲苯 为溶剂， 反应 2.5h， 生成 5-methyl-2-(3-methylphenyl)-2,4-dihydropyrazol-3-one
  参考文献：
  名称：

  Diversification of edaravone via palladium-catalyzed hydrazine cross-coupling: Applications against protein misfolding and oligomerization of beta-amyloid

  摘要：

  N-Aryl derivatives of edaravone were identified as potentially effective small molecule inhibitors of tau and beta-amyloid aggregation in the context of developing disease-modifying therapeutics for Alzheimer's disease (AD). Palladium-catalyzed hydrazine monoarylation protocols were then employed as an expedient means of preparing a focused library of 21 edaravone derivatives featuring varied N-aryl substitution, thereby enabling structure-activity relationship (SAR) studies. On the basis of data obtained from two functional biochemical assays examining the effect of edaravone derivatives on both fibril and oligomer formation, it was determined that derivatives featuring an N-biaryl motif were four-fold more potent than edaravone. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2015.11.022

文献信息

• Catalytic Asymmetric Addition of Diorganozinc Reagents to Pyrazole‐4,5‐Diones and Indoline‐2,3‐Diones
  作者：Rong‐Hui Wang、Ya‐Ling Li、Hong‐Jiao He、You‐Cai Xiao、Fen‐Er Chen

  DOI：10.1002/chem.202005081

  日期：2021.3

  The catalytic enantioselective diorganozinc additions to cyclic diketones including pyrazolin‐4,5‐diones and isatins have been developed. In the presence of morpholine‐containing chiral amino alcohol ligand, the corresponding chiral cyclic tertiary alcohols were produced in good to excellent yields (up to 97 %) and enantioselectivities (up to 95 % ee). The notable feature of this protocol includes

  已经开发了对环二酮（包括吡唑啉-4,5-二酮和靛红）的催化对映选择性二有机锌。在含有吗啉的手性氨基醇配体存在的情况下，相应的手性环状叔醇以良好至极佳的收率（高达97％）和对映选择性（高达95％ee）生产。该方案的显着特征包括温和的反应条件，无路易斯酸添加剂和宽泛的官能团耐受性。
• SO₂F₂ mediated transformation of pyrazolones into pyrazolyl fluorosulfates
  作者：Jing Leng、Hua-Li Qin

  DOI：10.1039/c9ob00903e

  日期：——

  The construction of a class of novel N-heterocyclic molecules containing both pyrazole and fluorosulfate functionalities was achieved through the reactions of pyrazolones with SO2F2 in good to excellent yields. The fluorosulfate moieties were utilized as versatile building blocks in the Suzuki coupling reaction and SuFEx click chemistry.

  通过吡唑啉酮与SO 2 F 2的反应，以良好至极好的收率，可以实现一类同时具有吡唑和氟硫酸盐官能团的新型N-杂环分子的构建。在Suzuki偶联反应和SuFEx click化学中，氟代硫酸盐部分被用作通用的结构单元。
• Iodine‐Catalyzed Construction of Dihydrooxepines via 3‐Methyl‐5‐Pyrazolones C−H Oxidation/Functionalization of Quinolines Cascade
  作者：Rong Zhang、Jun Wang、Weiwei Jin、Yonghong Zhang、Bin Wang、Yu Xia、Chenjiang Liu

  DOI：10.1002/ejoc.202100541

  日期：2021.7.22

  The iodine-catalyzed catalytic formal [3+3+1] annulation for the construction of a seven-membered O-heteocycle with quinoline is developed. This strategy involves a seven-membered dihydrooxepine with a broad substrate scope through a formal three-component tandem reaction. Further derivation of the target product produced a trioxabicycle scaffold, which formed the basic core of natural products and

  开发了碘催化的催化形式 [3+3+1] 环化，用于构建带有喹啉的七元 O-杂环。该策略涉及通过正式的三组分串联反应获得具有广泛底物范围的七元二氢氧杂环庚烷。目标产物的进一步衍生得到了三氧杂环骨架，形成了天然产物和药物分子的基本核心，广泛的底物范围显示了一种优雅的合成方法。
• Catalytic System‐Controlled Divergent Reaction Strategies for the Construction of Diversified Spiropyrazolone Skeletons from Pyrazolidinones and Diazopyrazolones
  作者：Feifei Fang、Shulei Hu、Chunpu Li、Qian Wang、Run Wang、Xu Han、Yu Zhou、Hong Liu

  DOI：10.1002/anie.202105857

  日期：2021.9.20

  system-controlled divergent reaction strategy was here reported to construct four types of intriguing spiroheterocyclic skeletons from simple and readily available starting materials via a precise chemical bond activation/[n+1] annulation cascade. The tetraazaspiroheterocyclic and trizazspiroheterocyclic scaffolds could be independently constructed by a selective N−N bond activation/[n+1] annulation cascade, a C(sp2)-H

  本文报道了一种催化系统控制的发散反应策略，通过精确的化学键活化/[ n +1] 环化级联，从简单易得的起始材料构建四种有趣的螺杂环骨架。四氮杂螺杂环和三氮杂螺杂环支架可以通过选择性 NN 键激活/[ n +1] 环化级联、C(sp 2 )-H 激活/[4+1] 环化和新型串联 C(sp 2 )-H/C(sp 3)−H 键活化/[4+1] 环化策略，以及广泛的底物、中等至优异的产率和有价值的转化。更重要的是，在这些转化中，我们首次捕捉到了不同催化体系下吡唑烷酮的 NN键活化和 C(sp 3 )-H 键活化。
• 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。