3-methyl-1,4-diphenyl-5-pyrazolone | 41927-54-2

• 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: 3-methyl-1,4-diphenyl-5-pyrazolone
• 英文别名: 2,5-diphenyl-4-methyl-2,3-pyrazol-1(5H)-one；1,4-Diphenyl-3-methyl-pyrazolin-5-on；3-Methyl-1.4-diphenyl-pyrazolon-(5)；5-methyl-2,5-diphenyl-1,2-dihydro-pyrazol-3-one；3-Methyl-1,4-diphenyl-1H-pyrazole-5(4H)-one；5-methyl-2,4-diphenyl-4H-pyrazol-3-one
• CAS: 41927-54-2
• 化学式: C₁₆H₁₄N₂O
• 分子量: 250.3
• InChiKey: UXFHZGKRWAEYAM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 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：

  N-苯基马来酰亚胺 、 3-methyl-1,4-diphenyl-5-pyrazolone 在 1-[3,5-双(三氟甲基)苯基]-3-[(1R,2R)-(-)-2-(二甲氨基)环己基]硫脲 作用下， 以 甲苯 为溶剂， 反应 14.0h， 以89%的产率得到3-(3-Methyl-5-oxo-1,4-diphenylpyrazol-4-yl)-1-phenylpyrrolidine-2,5-dione
  参考文献：
  名称：

  顺丁烯二酰亚胺的有机催化对映选择性吡唑-3-酮：反应性和立体化学过程†

  摘要：

  在有机合成中尚未广泛研究吡唑-3-酮的对映选择性合成。在这里我们报告了双官能硫脲催化剂催化的吡唑啉酮向马来酰亚胺的首次不对称加成。

  DOI：

  10.1039/c2ob06553c
• 作为产物：
  描述：

  苯乙酸乙酯 在 sodium hydride 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 反应 4.5h， 生成 3-methyl-1,4-diphenyl-5-pyrazolone
  参考文献：
  名称：

  Hydroxyl radical scavenging by edaravone derivatives: Efficient scavenging by 3-methyl-1-(pyridin-2-yl)-5-pyrazolone with an intramolecular base

  摘要：

  We synthesized various 3-methyl-1-phenyl-5-pyrazolone (edaravone) derivatives and evaluated their oxidation potential and hydroxyl radical scavenging activity. It was found 3-methyl-1-(pyridin-2-yl)-5-pyrazolone had a much higher ability to scavenge the radical than did edaravone itself. Its efficient radical scavenging activity was assumed to be due to the increase of its anion form, an active form, by a hydrogen-bonded intramolecular base.

  DOI：

  10.1016/j.bmcl.2006.09.005

文献信息

• One-pot synthesis of 5-(substituted-amino)pyrazoles
  作者：Dharmpal S Dodd、Rogelio L Martinez

  DOI：10.1016/j.tetlet.2004.04.017

  日期：2004.5

  An efficient and mild one-pot synthesis of substituted 5-alkylamino and/or 5-(arylamino)pyrazoles is described. A suitably decorated β-ketoamide, an aryl or alkyl hydrazine and Lawesson's reagent are suspended in THF/Py and gently heated to yield the requisite 5-aminopyrazoles.

  描述了取代的5-烷基氨基和/或5-（芳基氨基）吡唑的有效且温和的一锅合成。将适当修饰的β-酮酰胺，芳基或烷基肼和Lawesson试剂悬浮在THF / Py中，并轻轻加热，以生成所需的5-氨基吡唑。
• Isothiourea-catalysed enantioselective Michael addition of N-heterocyclic pronucleophiles to α,β-unsaturated aryl esters
  作者：Chang Shu、Honglei Liu、Alexandra M. Z. Slawin、Cameron Carpenter-Warren、Andrew D. Smith

  DOI：10.1039/c9sc04303a

  日期：——

  The isothiourea-catalysed enantioselective Michael addition of 3-aryloxindole and 4-substituted-dihydropyrazol-3-one pronucleophiles to α,β-unsaturated p-nitrophenyl esters is reported. This process generates products containing two contiguous stereocentres, one quaternary, in good yields and excellent enantioselectivities (>30 examples, up to > 95 : 5 dr and 99 : 1 er). This protocol harnesses the

  报道了异硫脲催化的 3-aryloxindole 和 4-取代的二氢吡唑-3-one 亲核试剂对 α,β-不饱和对硝基苯酯的对映选择性迈克尔加成。该过程产生的产物含有两个连续的立体中心，一个是四元的，产率高，对映选择性好（>30 个实例，高达 > 95 : 5 dr 和 99 : 1 er）。该协议利用对硝基苯氧化物的多功能能力来促进有效催化。与以前使用叔胺路易斯碱的方法（其中使用亲核试剂作为溶剂）相比，这项工作允许以化学计量数量使用定制的亲核试剂。
• New Series of Antiprion Compounds:  Pyrazolone Derivatives Have the Potent Activity of Inhibiting Protease-Resistant Prion Protein Accumulation
  作者：Ayako Kimata、Hidehiko Nakagawa、Ryo Ohyama、Tomoko Fukuuchi、Shigeru Ohta、Takayoshi Suzuki、Naoki Miyata

  DOI：10.1021/jm070688r

  日期：2007.10.1

  To find effective antiprion compounds, we synthesized and evaluated various pyrazolone derivatives. Seven of 19 compounds showed inhibition of PrP-res accumulation and the remarkably active compound 13 showed an IC50 value of 3 nM in both ScN2a and F3 cell lines. Findings from studies on physicochemical and biochemical properties suggest that the action mechanism of these compounds does not correlate

  为了找到有效的抗pr病毒化合物，我们合成并评估了各种吡唑啉酮衍生物。19种化合物中的7种显示出对PrP-res积累的抑制作用，而显着活性的化合物13在ScN2a和F3细胞系中的IC50值为3 nM。从理化和生物化学性质的研究发现表明，这些化合物的作用机理与任何抗氧化剂活性，任何羟基自由基清除活性或任何SOD样活性均不相关。
• Base promoted direct C4-arylation of 4-substituted-pyrazolin-5-ones with diaryliodonium salts
  作者：Song Mao、Xu Geng、Yang Yang、Xiaofei Qian、Shengying Wu、Jianwei Han、Limin Wang

  DOI：10.1039/c5ra03819g

  日期：——

  A metal-free approach for the C4-arylation of 4-substituted-pyrazolin-5-ones with diaryliodonium salts was developed. The reaction proceeded smoothly at room temperature in the presence of DMAP (4-dimethylaminopyridine). As a result, a wide range of desired multi-substituted pyrazolin-5-one derivatives were obtained in good to excellent yields (20–98%).

  开发了一种无金属的方法，用于将4-取代的吡唑啉-5-酮与二芳基碘鎓盐进行C4-芳基化。反应在室温下在DMAP（4-二甲基氨基吡啶）存在下顺利进行。结果，获得了多种所需的多取代的吡唑啉-5-酮衍生物，收率良好至优异（20-98％）。
• A Novel Route to 2,3-Pyrazol-1(5<i>H</i>)-ones via Palladium-Catalyzed Carbonylation of 1,2-Diaza-1,3-butadienes
  作者：Robert K. Boeckman,、Jessica E. Reed、Ping Ge

  DOI：10.1021/ol016565x

  日期：2001.11.1

  [GRAPHICS]A novel Pd(0)-catalyzed carbonylation of both isolable 1,2-diaza-1,3-butadienes and those generated in situ by extrusion of SO2 and CO2 from heterocyclic precursors is described. The reaction proceeds at room temperature to 110 degreesC under 1-2 atm of CO to afford 2,3-pyrazol-1(5H)-ones in good to excellent yields. The effect of catalyst structure and stability on the carbonylation reaction is evaluated.