5-methyl-2-(naphthalen-2-yl)-2,4-dihydro-3H-pyrazol-3-one | 107920-02-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 5-methyl-2-(naphthalen-2-yl)-2,4-dihydro-3H-pyrazol-3-one
• 英文别名: 3-Methyl-1-(naphthalen-2-yl)-1h-pyrazol-5(4h)-one；5-methyl-2-naphthalen-2-yl-4H-pyrazol-3-one
• CAS: 107920-02-5
• 化学式: C₁₄H₁₂N₂O
• 分子量: 224.262
• InChiKey: MPXVJKOGBNDSLG-UHFFFAOYSA-N

物化性质

• 沸点：
  435.4±14.0 °C(Predicted)
• 密度：
  1.21±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.14
• 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：

  5-methyl-2-(naphthalen-2-yl)-2,4-dihydro-3H-pyrazol-3-one 在 aluminum (III) chloride 、 碘苯二乙酸 、 四丁基碘化铵 、 caesium carbonate 作用下， 以 二氯甲烷 为溶剂， 反应 15.0h， 生成 1,9-dimethyl-3,7-di(naphthalen-2-yl)-3,7-dihydro[1,3]-dioxepino[4,5-c:7,6-c’]dipyrazole
  参考文献：
  名称：

  吡唑啉酮衍生物和二氯甲烷参与的 1,3-二氧杂环庚烷-稠合（三环）双吡唑的合成

  摘要：

  描述了一种简单而新颖的合成新型 1,3-二氧杂环庚烷（三环）双吡唑的方法。它涉及以二氯甲烷为亚甲基源的容易获得的吡唑啉酮衍生物的 Cs 2 CO 3介导的O烷基化，然后在温和条件下进行 PhI(OAc) 2介导的分子内氧化二杂芳基偶联。这种可扩展的方案用于制备有价值的新型 1,3-二氧杂环庚烷（三环）双吡唑，可在药物或材料化学中找到应用。

  DOI：

  10.1021/acs.joc.1c03121
• 作为产物：
  描述：

  对甲基苯磺酸-2-萘酯 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 1.25h， 生成 5-methyl-2-(naphthalen-2-yl)-2,4-dihydro-3H-pyrazol-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

• Electrochemical synthesis of versatile ammonium oxides under metal catalyst-, exogenous-oxidant-, and exogenous-electrolyte-free conditions
  作者：Yong Yuan、Liang-Sen Li、Lin Zhang、Feng Wang、Lin Jiang、Lin Zuo、Qi Wang、Jian-Guo Hu、Aiwen Lei

  DOI：10.1039/d1cc00486g

  日期：——

  An electrochemical oxidative cross-coupling reaction between 2.5-substituted-pyrazolin-5-ones and ammonium thiocyanate has been developed, which resulted in a series of unprecedented cross-coupling products under metal catalyst-, exogenous-oxidant-, and exogenous-electrolyte-free conditions. It is worth noting that since the resulting cross-coupling products are nearly insoluble in MeCN, the pure product

  已经开发了2.5-取代的吡唑啉-5-酮与硫氰酸铵之间的电化学氧化交叉偶联反应，从而在金属催化剂，外源氧化剂和外源电解质-的作用下产生了一系列前所未有的交叉偶联产物。免费条件。值得注意的是，由于所得的交叉偶联产物几乎不溶于MeCN，因此无需硅胶柱纯化即可提供纯产物。此外，制备的氧化铵是用于合成官能化吡唑衍生物的通用构建基。
• Regioselectivity Switch in Palladium‐Catalyzed Allenylic Cycloadditions of Allenic Esters: [4+1] or [4+3] Cycloaddition/Cross‐Coupling
  作者：Long Li、Pengfei Luo、Yuhua Deng、Zhihui Shao

  DOI：10.1002/anie.201901511

  日期：2019.3.26

  The first Pd‐catalyzed asymmetric allenylic [4+1] cycloaddition was successfully developed. Alternatively, tuning the Pd catalyst switched the reactivity toward an unprecedented [4+3] cycloaddition/cross‐coupling. Ligands play a vital role in controlling the reaction pathway, allowing highly selective access to different products from identical substrates. Biological evaluation of the obtained compounds

  首次成功开发了Pd催化的不对称烯丙基[4 + 1]环加成反应。另外，调整Pd催化剂可将反应性转向前所未有的[4 + 3]环加成/交叉偶联。配体在控制反应路径中起着至关重要的作用，可以高度选择性地从相同的底物中获得不同的产物。对获得的化合物的生物学评估导致发现新的抗肿瘤靶标。提出了一种可能的机理，暗示了两个有趣的催化循环，用于与钯-丁二烯基进行环加成反应。这项研究还证明了烯丙酸酯作为1,4-双亲电子试剂和C 4合成子参与环加成反应的潜力和实用性。
• Zinc chloride catalyzed stereoselective construction of spiropyrazolone tetrahydroquinolines via tandem [1,5]-hydride shift/cyclization sequence
  作者：Tuan Zhao、Huanrui Zhang、Longchen Cui、Jingping Qu、Baomin Wang

  DOI：10.1039/c5ra18471a

  日期：——

  A zinc chloride catalyzed tandem 1,5-hydride shift/cyclization process to form spiropyrazolone terahydroquinoline derivatives is developed. A series of new spiropyrazolone derivatives were obtained in good to high yields with good to excellent diastereoselectivities (up to 95% yield, >95 : 5 dr). Additionally, the spiropyrazolone derivatives could be converted into the corresponding novel spriopyrazolines

  开发了氯化锌催化串联1,5-氢化物转变/环化工艺以形成螺吡唑酮四氢喹啉衍生物。以高至高收率获得了一系列新的螺并吡唑啉酮衍生物，非对映选择性很好（高达95％，> 95：5 dr）。另外，螺并吡唑啉酮衍生物可以转化为相应的新型螺并吡唑啉。
• Rhodium‐Catalyzed [4+2] Annulation of N‐Aryl Pyrazolones with Diazo Compounds To Access Pyrazolone‐Fused Cinnolines
  作者：Chih‐Yu Lin、Wan‐Wen Huang、Ying‐Ti Huang、Sandip Dhole、Chung‐Ming Sun

  DOI：10.1002/ejoc.202101005

  日期：2021.9.21

  An efficient synthesis of novel dinitrogen-fused heterocycles, such as pyrazolo[1,2-a]cinnoline derivatives, has been accomplished by the rhodium(III)-catalyzed reaction of N-arylpyrazol-5-ones with diazo compounds. This reaction proceeds through a cascade C−H activation/intramolecular cyclization under mild reaction conditions and features a broad substrate scope.

  新型二氮稠合杂环的有效合成，例如吡唑并[1,2- a ]肉啉衍生物，已通过铑(III)催化的N-芳基吡唑-5-酮与重氮化合物的反应完成。该反应在温和的反应条件下通过级联 CH 活化/分子内环化进行，具有广泛的底物范围。
• One-pot cascade synthesis of N-methoxyisoquinolinediones via Rh(<scp>iii</scp>)-catalyzed carbenoid insertion C–H activation/cyclization
  作者：Jingjing Shi、Jie Zhou、Yunnan Yan、Jinlong Jia、Xuelei Liu、Huacan Song、H. Eric Xu、Wei Yi

  DOI：10.1039/c4cc08407a

  日期：——

  new, mild and versatile method for one-pot cascade synthesis of diverse N-methoxyisoquinolinediones via Rh(III)-catalyzed regioselective carbenoid insertion C-H activation/cyclization of N-methoxybenzamides with alpha-diazotized Meldrum's acid has been achieved. Extension of the developed Rh(III) catalysis for building new analogs of the marketed drug Edaravone has also been demonstrated.

  在这里，已经实现了一种新的，温和且通用的方法，该方法可通过Rh（III）催化的区域选择性类胡萝卜素插入反应，通过N-甲氧基苯甲酰胺与α-重氮基的Meldrum酸进行CH活化/环化，一锅级联合成各种N-甲氧基异喹啉二酮。还证明了开发的Rh（III）催化作用的扩展，以构建市售药物Edaravone的新类似物。