2-(biphenyl-4-yl)-5-methyl-2,4-dihydropyrazol-3-one | 18048-66-3

• 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-(biphenyl-4-yl)-5-methyl-2,4-dihydropyrazol-3-one
• 英文别名: 2-[1,1a(2)-Biphenyl]-4-yl-2,4-dihydro-5-methyl-3H-pyrazol-3-one；5-methyl-2-(4-phenylphenyl)-4H-pyrazol-3-one
• CAS: 18048-66-3
• 化学式: C₁₆H₁₄N₂O
• 分子量: 250.3
• InChiKey: ZPQSYRQQCSMFMR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 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：

  二氯甲烷 、 2-(biphenyl-4-yl)-5-methyl-2,4-dihydropyrazol-3-one 在 四丁基碘化铵 、 caesium carbonate 作用下， 反应 10.0h， 以41%的产率得到bis{[1-([1,1’-biphenyl]-4-yl)-3-methyl-1H-pyrazol-5-yl]oxy}methane
  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：

  4-氯联苯 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 1.0h， 生成 2-(biphenyl-4-yl)-5-methyl-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

• Diversification of edaravone via palladium-catalyzed hydrazine cross-coupling: Applications against protein misfolding and oligomerization of beta-amyloid
  作者：Mark A. MacLean、Elena Diez-Cecilia、Christopher B. Lavery、Mark A. Reed、Yanfei Wang、Donald F. Weaver、Mark Stradiotto

  DOI：10.1016/j.bmcl.2015.11.022

  日期：2016.1

  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.
• Synthesis of 1,3-Dioxepine-Fused (Tricyclic) Bispyrazoles Involved with Pyrazolone Derivatives and Dichloromethane
  作者：Zongqiang Song、Kai Zhu、Hongqiang Jiang、Hengfa Gong、Zenghui Ye、Fengzhi Zhang

  DOI：10.1021/acs.joc.1c03121

  日期：2022.3.18

  3-dioxepine-fused (tricyclic) bispyrazoles is described. It involves a Cs2CO3-mediated O-alkylation of readily available pyrazolone derivatives with dichloromethane as the methylene source followed by PhI(OAc)2-mediated intramolecular oxidative biheteroaryl coupling under mild conditions. This scalable protocol was applied for the preparation of valuable and novel 1,3-dioxepine-fused (tricyclic) bispyrazoles

  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。