3-(3-chlorophenyl)-1-phenyl-1H-pyrazol-5(4H)-one | 118049-74-4

• 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: 3-(3-chlorophenyl)-1-phenyl-1H-pyrazol-5(4H)-one
• 英文别名: 3-m-chlorophenyl-1-phenyl-2-pyrazoline-5-one；5-(3-chlorophenyl)-2-phenyl-4H-pyrazol-3-one
• CAS: 118049-74-4
• 化学式: C₁₅H₁₁ClN₂O
• 分子量: 270.718
• InChiKey: LZTKRCIWQWVOOA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 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：

  3-(3-chlorophenyl)-1-phenyl-1H-pyrazol-5(4H)-one 、 五氟苯腈 在 caesium carbonate 作用下， 以 四氢呋喃 为溶剂， 以70%的产率得到4-((3-(3-chlorophenyl)-1-phenyl-1H-pyrazol-5-yl)oxy)-2,3,5,6-tetrafluorobenzonitrile
  参考文献：
  名称：

  Base initiated aromatization/C O bond formation: a new entry to O-pyrazole polyfluoroarylated ethers

  摘要：

  A base initiated intermolecular SNAr reaction of pyrazolones with polyfluoroarenes was developed. The process involved the isomerization aromatization of pyrazolone followed by the C-O bond formation via the selective C-F bond cleavage. With this strategy, a wide range of O-pyrazole polyfluoroarylated ethers bearing diverse functional groups were synthesized in mild to good yields. Additionally, our method was also applied to the isoxazol substrates. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2014.09.129
• 作为产物：
  描述：

  3-氯苯乙酮 在 sodium hydride 、 溶剂黄146 作用下， 以 乙醇 为溶剂， 生成 3-(3-chlorophenyl)-1-phenyl-1H-pyrazol-5(4H)-one
  参考文献：
  名称：

  Base initiated aromatization/C O bond formation: a new entry to O-pyrazole polyfluoroarylated ethers

  摘要：

  A base initiated intermolecular SNAr reaction of pyrazolones with polyfluoroarenes was developed. The process involved the isomerization aromatization of pyrazolone followed by the C-O bond formation via the selective C-F bond cleavage. With this strategy, a wide range of O-pyrazole polyfluoroarylated ethers bearing diverse functional groups were synthesized in mild to good yields. Additionally, our method was also applied to the isoxazol substrates. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2014.09.129

文献信息

• Enantioselective Copper-Catalyzed [3 + 3] Cycloaddition of Tertiary Propargylic Esters with 1<i>H</i>-Pyrazol-5(4<i>H</i>)-ones toward Optically Active Spirooxindoles
  作者：You-Wei Xu、Ling Li、Xiang-Ping Hu

  DOI：10.1021/acs.orglett.0c03587

  日期：2020.12.18

  A copper-catalyzed enantioselective [3 + 3] cycloaddition of 3-ethynyl-2-oxoindolin-3-yl acetates with 1H-pyrazol-5(4H)-ones for the construction of optically active spirooxindoles bearing a spiro all-carbon quaternary stereocenter has been realized. With a combination of Cu(OTf)2 and chiral tridentate ketimine P,N,N-ligand as the catalyst, the reaction displayed broad substrate scopes, good yields

  铜催化的3-乙炔基-2-氧代吲哚-3-基乙酸乙酸酯与1 H-吡唑-5（4 H）-的铜对映体选择性[3 + 3]环加成反应，用于构建带有螺全碳的旋光螺硫醇四元立体中心已实现。以Cu（OTf）2和手性三齿酮亚胺P，N，N-配体为催化剂，该反应显示出较宽的底物范围，良好的收率和高对映选择性。这代表了使用叔炔丙基酯作为双亲电子试剂进行手性螺环骨架的首次催化不对称炔丙基环加成反应。
• A Convenient Microwave-Assisted Propylphosphonic Anhydride (T3P^®) Mediated One-Pot Pyrazolone Synthesis
  作者：Matthieu Desroses、Marie-Caroline Jacques-Cordonnier、Sabin Llona-Minguez、Sylvain Jacques、Tobias Koolmeister、Thomas Helleday、Martin Scobie

  DOI：10.1002/ejoc.201300380

  日期：2013.9

  This paper describes a facile, efficient, and clean synthesis of various pyrazolones by employing T3P® as a catalyst and performing the reaction under microwave irradiation. This two-step, one-pot reaction proceeded readily and tolerated a variety of functional groups. A wide range of pyrazolone derivatives were obtained in good to excellent yields.

  本文描述了通过使用 T3P® 作为催化剂并在微波辐射下进行反应，轻松、高效和清洁地合成各种吡唑啉酮。这种两步一锅的反应很容易进行并且可以耐受各种官能团。以良好到极好的收率获得了范围广泛的吡唑啉酮衍生物。
• One-Pot Asymmetric Synthesis of Spiropyrazolone-Linked Cyclopropanes and Benzofurans through a General Michael Addition/Chlorination/Nucleophilic Substitution Sequence
  作者：Hong Lu、Huan-Xin Zhang、Chang-Yin Tan、Jin-Yu Liu、Hao Wei、Peng-Fei Xu

  DOI：10.1021/acs.joc.9b01454

  日期：2019.8.16

  A sequential and general strategy has been successfully developed for the synthesis of spiropyrazolone scaffolds. This intriguing transformation of the asymmetric multicomponent catalysis process was realized with the combination of Michael addition/chlorination/nucleophilic substitution in a one-pot sequence, giving rise to a series of spiropyrazolones with fully substituted cyclopropanes and spi

  已经成功地开发了用于合成螺吡唑酮支架的顺序和通用策略。一键顺序结合迈克尔加成/氯化/亲核取代反应，实现了不对称多组分催化过程的这一引人入胜的转化，从而产生了一系列具有完全取代的环丙烷的螺并吡唑并酮和螺-二氢苯并呋喃，其中连续的立体构型中心良好产生具有优异立体选择性的化合物。
• Copper-catalyzed propargylic [3+3] cycloaddition with 1<i>H</i>-pyrazol-5(4<i>H</i>)-ones: enantioselective access to optically active dihydropyrano[2,3-<i>c</i>]pyrazoles
  作者：Ling Li、Zhen-Ting Liu、Xiang-Ping Hu

  DOI：10.1039/c8cc05706k

  日期：——

  A copper-catalyzed asymmetric propargylic [3+3] cycloaddition with 1H-pyrazol-5(4H)-ones as C,O-bisnucleophiles through the desilylation-activated strategy has been developed. With the catalysis of Cu(OAc)2·H2O in combination with a chiral tridentate P,N,N-ligand, the reaction displayed a broad substrate scope, and thus provided a variety of chiral dihydropyrano[2,3-c]pyrazoles in high yields and with

  通过去甲硅烷基化活化策略，开发了以1 H-吡唑-5（4 H）-为C，O-双亲核试剂的铜催化不对称炔丙基[3 + 3]环加成反应。Cu（OAc）2 ·H 2 O与手性三齿P，N，N-配体结合催化，反应显示出较宽的底物范围，从而提供了多种手性二氢吡喃[2,3- c ]吡唑类化合物的收率高（对映体选择性高达96％ee）。
• Organocatalytic diastereo- and enantioselective conjugate addition of pyrazol-3-ones to 3-trifluoroethylidene oxindoles with a newly developed squaramide catalyst
  作者：Zhao Han、Jiaping Jin、Alemayehu Gashaw Woldegiorgis、Xufeng Lin

  DOI：10.1039/d2ra05088a

  日期：——

  An efficient organocatalytic conjugated addition reaction of pyrazol-3-ones with 3-trifluoroethylidene oxindoles has been developed for the synthesis of enantioenriched triflouromethylated indolin-2-ones bearing adjacent tertiary chiral centers in good yields and good to excellent diastereo- and enantioselectivities. The use of a newly developed chiral spirobiindane-derived squaramide catalyst is essential

  吡唑-3-酮与3-三氟亚乙基羟吲哚的高效有机催化共轭加成反应已被开发用于以良好的收率和良好的非对映选择性和对映选择性合成具有相邻叔手性中心的对映富集的三氟甲基化二氢吲哚-2-酮。使用新开发的手性螺二茚衍生方酰胺催化剂对于实现高非对映和对映选择性至关重要。