5-Naphthalen-2-yl-2-phenyl-2,4-dihydro-pyrazol-3-one | 78120-51-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 5-Naphthalen-2-yl-2-phenyl-2,4-dihydro-pyrazol-3-one
• 英文别名: 5-naphthalen-2-yl-2-phenyl-4H-pyrazol-3-one
• CAS: 78120-51-1
• 化学式: C₁₉H₁₄N₂O
• 分子量: 286.333
• InChiKey: LZZOAOXRNQCBIP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.98
• 重原子数：
  22.0
• 可旋转键数：
  2.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  32.67
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  5-Naphthalen-2-yl-2-phenyl-2,4-dihydro-pyrazol-3-one 在 盐酸 、 potassium carbonate 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 生成
  参考文献：
  名称：

  Pd催化芳基硼酸不对称加成到吡唑啉酮酮亚胺

  摘要：

  据报道，使用钯/手性N , N '-二磺酰基双咪唑啉 (Bim) 催化系统将芳基硼酸不对称加成到吡唑啉酮酮亚胺中，产生了 25 个对映体富集的 4-氨基-5-吡唑啉酮实例，带有一个季碳立体中心，占 60-91%产量和 81-98% ee。该反应证明了吡唑啉酮酮亚胺和芳基硼酸的显着相容性，使对映选择性获得带有α-叔胺的手性氮杂杂环。

  DOI：

  10.1002/adsc.202101137
• 作为产物：
  描述：

  2-萘乙酮 在 sodium hydride 、 溶剂黄146 作用下， 以 乙醇 为溶剂， 生成 5-Naphthalen-2-yl-2-phenyl-2,4-dihydro-pyrazol-3-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。
• Synthesis of Spiropentadiene Pyrazolones by Rh(III)-Catalyzed Formal sp³ C–H Activation/Annulation
  作者：Jiuan Zheng、Panpan Li、Meng Gu、Aijun Lin、Hequan Yao

  DOI：10.1021/acs.orglett.7b00930

  日期：2017.6.2

  pyrazolones with alkynes has been developed. This reaction provides a convenient route to synthesize spiropentadiene pyrazolones in good to excellent yields at room temperature, exhibiting good functional group tolerance, gram scalability, and high regioselectivity. Of note, the α-arylidene pyrazolone was introduced as a novel C3 synthon in C–H activation/annulation.

  已经开发了用Rh催化烯醇定向的形式sp 3 C–H活化/环炔基的α-亚芳基吡唑啉酮。该反应提供了在室温下以良好至优异的产率合成螺戊二烯吡唑啉酮的便利途径，表现出良好的官能团耐受性，克可扩展性和高区域选择性。值得注意的是，α-亚芳基吡唑啉酮是在C–H活化/环化反应中作为新型C3合成子引入的。
• Asymmetric, Three-Component, One-Pot Synthesis of Spiropyrazolones and 2,5-Chromenediones from Aldol Condensation/NHC-Catalyzed Annulation Reactions
  作者：Lei Wang、Sun Li、Pankaj Chauhan、Daniel Hack、Arne R. Philipps、Rakesh Puttreddy、Kari Rissanen、Gerhard Raabe、Dieter Enders

  DOI：10.1002/chem.201600515

  日期：2016.4.4

  A novel one‐pot, three‐component diastereo‐ and enantioselective synthesis of spiropyrazolones has been developed involving the aldol condensation of an enal to generate α,β‐unsaturated pyrazolones, which react with a second equivalent of enal through an N‐heterocyclic carbene (NHC)‐catalyzed [3+2] annulation. The desired spirocyclopentane pyrazolones are obtained in moderate to good yields and good

  已开发出一种新颖的单锅，三组分，对映体和对映体对吡咯并酮的对映体合成方法，该方法包括将烯醛进行羟醛缩合反应生成α，β-不饱和吡唑酮，并通过N杂环卡宾与第二当量的烯醛反应（ NHC）催化的[3 + 2]环空。所需的螺环戊烷吡唑啉酮以中等至良好的产率和良好至优异的立体选择性获得。另外，从循环的1，3-二酮开始，可通过[2 + 4]环空获得2,5-铬二酮。
• Synthesis of Chiral Pyrazolone and Spiropyrazolone Derivatives through Squaramide-Catalyzed Reaction of Pyrazolin-5-ones with <i>o</i>-Quinone Methides
  作者：Ji Zhou、Wen-Jun Huang、Guo-Fang Jiang

  DOI：10.1021/acs.orglett.8b00025

  日期：2018.2.16

  A bifunctional squaramide-catalyzed reaction of pyrazolin-5-ones with o-quinone methides in situ generated from 2-(1-tosylalkyl)phenols has been successfully developed, providing a facile access to chiral pyrazolones with high enantioselectivities. In addition, the chiral spiropyrazolones with adjacent tertiary and quaternary stereogenic centers can also be obtained through cascade chlorination/cyclization

  已成功开发了吡唑啉-5-酮与由2-（1-甲苯磺酰基烷基）苯酚原位生成的邻醌甲基化物的双官能方酰胺催化的反应，可轻松获得具有高对映选择性的手性吡唑啉酮。此外，还可以通过手性吡唑啉酮的级联氯化/环化来获得具有相邻的叔和四级立体异构中心的手性螺吡唑并酮。
• 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）。