1-(4-methoxyphenyl)pyrazolidin-3-one | 6107-53-5

• 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: 1-(4-methoxyphenyl)pyrazolidin-3-one
• 英文别名: 1-<4-Methoxy-phenyl>-pyrazolidon-(3)；1-(4-Methoxy-phenyl)-pyrazolidin-3-on
• CAS: 6107-53-5
• 化学式: C₁₀H₁₂N₂O₂
• 分子量: 192.217
• InChiKey: JEDFGCYVWYGWAK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  41.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-(4-methoxyphenyl)pyrazolidin-3-one 在 三乙胺 、 lithium diisopropyl amide 作用下， 以 二氯甲烷 为溶剂， 反应 1.75h， 生成 4-(2-Methoxy-ethyl)-1-(4-methoxy-phenyl)-pyrazolidin-3-one
  参考文献：
  名称：

  5-Lipoxygenase inhibitors: the synthesis and structure-activity relationships of a series of 1-phenyl-3-pyrazolidinones

  摘要：

  A series of analogues of the 5-lipoxygenase inhibitor 1-phenyl-3-pyrazolidinone (phenidone, 1a) has been prepared via two complementary new synthetic methods. The reaction of various electrophiles with the dianion of 1a or with an N-silylpyrazolidinone anion gave the desired 4-substituted pyrazolidinones (Scheme I and II). A new procedure was developed for the resolution of 4-substituted pyrazolidinones (Scheme V). A regression study on 21 compounds in this series showed a correlation of increased inhibitor potency (pIC50) with increased compound lipophilicity (log P) and with an N-phenyl electronic effect as measured by the C-13 NMR chemical shift parameter CNMR1' (R2 = 0.79). The most potent 5-lipoxygenase inhibitor in this series was 4-(ethylthio)-1-phenyl-3-pyrazolidinone (1n) with an IC50 of 60 nM. Another member of this series, 4-(2-methoxyethyl)-1-phenyl-3-pyrazolidinone (1f, IC50 = 0-48-mu-M), although less potent than 1n, was better tolerated in the whole animal relative to phenidone (1a) and also displayed good oral activity in two models of 5-lipoxygenase inhibition. On the basis of a structure-activity relationship study, a mechanism for the inhibition of 5-lipoxygenase by this class of inhibitors was proposed.

  DOI：

  10.1021/jm00109a006
• 作为产物：
  描述：

  丙烯酰胺 、 (4-甲氧基苯基)肼 在 乙醇 、 sodium methylate 作用下， 生成 1-(4-methoxyphenyl)pyrazolidin-3-one
  参考文献：
  名称：

  Production of 3-pyrazolidones

  摘要：

  公开号：

  US02704762A1

文献信息

• Nucleophilic Substitution of Azide Acting as a Pseudo Leaving Group: One-Step Synthesis of Various Aza Heterocycles
  作者：Christelle Doebelin、Martine Schmitt、Cyril Antheaume、Jean-Jacques Bourguignon、Frédéric Bihel

  DOI：10.1021/jo401738f

  日期：2013.11.15

  The reaction of 3-azidopropanoic acid with the carbodiimide-based coupling reagent DIC leads to a six-membered-ring intermediate acting as a versatile precursor to a diverse set of aza heterocycles, including mono-, bi-, and tricyclic compounds.

  3-叠氮基丙酸与基于碳二亚胺的偶联剂DIC的反应导致六元环中间体充当多种氮杂杂环（包括单环，双环和三环化合物）的多用途前体。
• Rhodium-catalyzed redox-neutral coupling of phenidones with alkynes
  作者：Zhoulong Fan、Heng Lu、Wei Li、Kaijun Geng、Ao Zhang

  DOI：10.1039/c7ob01271c

  日期：——

  A switchable synthesis of N-substituted indole derivatives from phenidones via rhodium-catalyzed redox-neutral C–H activation has been achieved. In this protocol, we firstly disclosed that the reactivity of Rh(III) catalysis could be enhanced through employing palladium acetate as an additive. Some representative features include external oxidant-free, applicable to terminal alkynes, short reaction

  通过铑催化的氧化还原中性CH活化，可从苯二酮中可合成N取代的吲哚衍生物。在该协议中，我们首先公开了通过使用乙酸钯作为添加剂可以增强Rh（III）催化的反应性。一些代表性功能包括：无外部氧化剂，适用于末端炔烃，反应时间短，操作简便。有效合成抗癌PARP-1抑制剂的经济合成进一步证明了该方法的实用性。
• Rhodium(III)-Catalyzed [4+3] Annulation of <i>N</i>-Aryl-pyrazolidinones and Propargylic Acetates: Access to Benzo[<i>c</i>][1,2]diazepines
  作者：Tingfang Li、Zi Yang、Zhenyu Song、Remi Chauvin、Xiuling Cui

  DOI：10.1021/acs.orglett.0c01139

  日期：2020.6.5

  The generation of 2,3-dihydro-benzo[c][1,2]diazepine derivatives via rhodium(III)-catalyzed [4+3] annulation of pyrazolidinones and propargylic acetates is disclosed. The reaction proceeds smoothly under relatively mild conditions from propargylic acetates as novel C3 synthons. A range of dinitrogen-fused heterocyclic compounds are readily accessed by this approach.

  公开了通过铑（III）催化的吡唑烷酮和乙酸炔丙基酯的[4 + 3]环化反应生成2，3-二氢-苯并[ c ] [1,2]二氮杂卓衍生物。在相对温和的条件下，由炔丙基乙酸酯作为新型C 3合成子，可使反应平稳进行。通过该方法可以容易地获得许多二氮稠合的杂环化合物。
• Rapid Construction of Hexacyclic Indolines via the Ru(II)-Catalyzed C–H Activation Initiated Cascade Cyclization of Phenidones with Enynones
  作者：Yang Li、Yongzhuang Wang、Xiaoli Huang、Yan Shi、Yuhai Tang、Jiao Jiao、Jing Li、Silong Xu

  DOI：10.1021/acs.orglett.1c04133

  日期：2022.1.14

  initiated indole formation/Diels–Alder reaction/iminium ion cyclization sequence, which afforded hexacyclic indolines as single diastereomer in good to excellent yields with a broad substrate scope under mild conditions. The reaction features the simultaneous generation of five new chemical bonds and four new rings in one pot, providing a rapid and concise approach toward polycyclic indoline alkaloids and

  通过 Ru(II) 催化的 C-H 活化引发的吲哚形成/Diels-Alder 反应/亚胺离子环化序列，开发了一种高效的苯尼酮和烯炔酮级联环化，以良好至优异的产率提供六环二氢吲哚作为单一非对映体在温和条件下具有广泛的底物范围。该反应的特点是在一锅中同时产生五个新的化学键和四个新的环，为多环二氢吲哚生物碱及其类似物提供了一种快速而简洁的方法。
• Rh^III-Catalysed Hydrazine-Directed C(sp²)-H Amination of Phenidones with<i>N</i>-Alkyl-<i>O</i>-benzoyl-hydroxylamines
  作者：Yu Xue、Zhoulong Fan、Xiaolong Jiang、Kui Wu、Meining Wang、Chunyong Ding、Qizheng Yao、Ao Zhang

  DOI：10.1002/ejoc.201402999

  日期：2014.11

  A RhIII-catalysed ortho C–H amination of phenidones under mild conditions was developed using N-alkyl-O-benzoyl-hydroxylamines as aminating agents, and with a cyclic hydrazine moiety as a directing group, yields of up to 97 % and a high functional group tolerance were observed. This strategy offers an alternative route for the synthesis of amino analogues of the 5-lipoxygenase inhibitor phenidone, and

  使用 N-烷基-O-苯甲酰基-羟胺作为胺化剂，并以环肼部分作为导向基团，在温和条件下开发了 RhIII 催化的苯乙酮邻位 C-H 胺化，产率高达 97%，并且观察到官能团耐受性。该策略为合成 5-脂氧合酶抑制剂菲尼酮的氨基类似物提供了另一种途径，并且该产品对于进一步的官能团转化很有价值。