5-methyl-2-[4-(trifluoromethyl)phenyl]-2,4-dihydropyrazol-3-one | 118031-38-2

• 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-[4-(trifluoromethyl)phenyl]-2,4-dihydropyrazol-3-one
• 英文别名: 5-methyl-2-(4-(trifluoromethyl)phenyl)-2,4-dihydro-3H-pyrazol-3-one；5-methyl-2-[4-(trifluoromethyl)phenyl]-4H-pyrazol-3-one
• CAS: 118031-38-2
• 化学式: C₁₁H₉F₃N₂O
• 分子量: 242.2
• InChiKey: XOAVQFOOGPXSPI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  32.7
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  5-methyl-2-[4-(trifluoromethyl)phenyl]-2,4-dihydropyrazol-3-one 在 碘化铵 、 四丁基硝酸铵 作用下， 以 二甲基亚砜 、 乙腈 为溶剂， 以62%的产率得到
  参考文献：
  名称：

  电化学诱导的吡唑啉酮的 C(sp3)-H 脱氢三聚化为三吡唑啉酮

  摘要：

  在无金属和无化学氧化剂的条件下，电化学诱导的吡唑啉酮C(sp 3 )-H 脱氢三聚化为三吡唑啉酮。这种电化学氧化策略可以很容易地扩大用于合成生物三吡唑啉酮，这有利于实际应用。

  DOI：

  10.1002/ejoc.202100988
• 作为产物：
  描述：

  对氯三氟甲苯 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 1.0h， 生成 5-methyl-2-[4-(trifluoromethyl)phenyl]-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。
• Metal-free direct construction of sulfenylated pyrazoles via the NaOH promoted sulfenylation of pyrazolones with aryl thiols
  作者：Xiaoxia Liu、Huanhuan Cui、Daoshan Yang、Shicui Dai、Tiantian Zhang、Jingyu Sun、Wei Wei、Hua Wang

  DOI：10.1039/c6ra09739a

  日期：——

  A convenient and cost-effective NaOH-promoted direct sulfenylation of pyrazolones with aryl thiols has been developed under mild and metal-free conditions.

  一种方便且具有成本效益的NaOH促进的在温和无金属条件下，用芳基硫醇直接对吡唑酮进行砜化的方法已经被开发出来。
• Highly Stereoselective Synthesis of Spiropyrazolones
  作者：Andrea-Nekane R. Alba、Alex Zea、Guillem Valero、Teresa Calbet、Merce Font-Bardía、Andrea Mazzanti、Albert Moyano、Ramon Rios

  DOI：10.1002/ejoc.201001452

  日期：2011.3

  The synthesis of spiro compounds through a Michael–Michael–aldol reaction is reported. The reaction affords spiropyrazolone derivatives in good yields, in almost diastereo- and enantiopure form, and is catalyzed by diphenylprolinol derivatives. The reaction showed strong nonlinear effects. Remarkably, when a catalyst with 70 % ee is used, the reaction still affords the final spiro compound in almost

  报道了通过迈克尔-迈克尔-羟醛反应合成螺环化合物。该反应以良好的收率提供几乎非对映纯和对映纯形式的螺吡唑啉酮衍生物，并由二苯基脯氨醇衍生物催化。该反应表现出很强的非线性效应。值得注意的是，当使用 70% ee 的催化剂时，反应仍然提供几乎非对映纯和对映纯形式的最终螺环化合物。
• Thrombopoietin mimetics
  申请人：——

  公开号：US20040019190A1

  公开（公告）日：2004-01-29

  Invented are non-peptide TPO mimetics. Also invented are novel processes and intermediates used in the preparation of the presently invented compounds. Also invented is a method of treating thrombocytopenia, in a mammal, including a human, in need thereof which comprises administering to such mammal an effective amount of a selected hydroxy- 1 -azobenzene derivative.

  发明了非肽类TPO类似物。还发明了用于制备目前发明的化合物的新工艺和中间体。还发明了一种治疗血小板减少症的方法，包括给予需要的哺乳动物，包括人类，有效量的选择性羟基-1-偶氮苯衍生物。
• 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。