2-(2-(1-(4-methoxyphenyl)ethylidene)hydrazinyl)pyridine | 82664-05-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 2-(2-(1-(4-methoxyphenyl)ethylidene)hydrazinyl)pyridine
• 英文别名: N-[1-(4-methoxyphenyl)ethylideneamino]pyridin-2-amine
• CAS: 82664-05-9
• 化学式: C₁₄H₁₅N₃O
• 分子量: 241.293
• InChiKey: KXDVQPOLXHNQLU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-(2-(1-(4-methoxyphenyl)ethylidene)hydrazinyl)pyridine 在 sodium acetate 、 乙酸酐 、 三氯氧磷 作用下， 反应 6.0h， 生成 (E)-1-ethyl-3,3-dimethyl-2-(2-(3-(4-methoxyphenyl)-1-(pyridin-2-yl)-1H-pyrazol-4-yl)vinyl)-3H-indolium iodide
  参考文献：
  名称：

  基于半花菁官能化的N-（2-吡啶基）吡唑类比色氰感测的新型D-π-A染料的合成

  摘要：

  在此，提供了一种基于半花菁官能化的N-（2-吡啶基）吡唑的用于色度氰化物传感的D-π-A有机染料新家族。这些染料通过阴离子对染料亚胺基团的亲核攻击而中断D–π–A系统，从而显示出对CN –的高选择性和灵敏度（LOD高达9.9×10 –7 m）。

  DOI：

  10.1002/ejoc.201901178
• 作为产物：
  描述：

  2-溴吡啶 在 盐酸 、 一水合肼 作用下， 以 乙醇 为溶剂， 反应 8.0h， 生成 2-(2-(1-(4-methoxyphenyl)ethylidene)hydrazinyl)pyridine
  参考文献：
  名称：

  Synthesis and evaluation of analgesic, antiinflammatory and antiplatelet properties of new 2-pyridylarylhydrazone derivatives

  摘要：

  This work describes recent results from our research program aiming at the synthesis and pharmacological evaluation of new compounds acting as antiinflammatory, analgesic and platelet antiaggregatory. In this paper the synthesis and the pharmacological profile as analgesic, antiinflammatory and anti-platelet of new functionalized 2-pyridylarylhydrazone derivatives 5a-r are discussed. This class of N-heterocyclic derivatives represents a new series of prototype candidates with analgesic and antiinflammatory properties possessing also an important anti-aggregating activity. The pharmacological results herein disclosed suggest that the antiinflammatory and analgesic activities of these new pyridynehydrazone derivatives observed in the carrageenan pleurisy model and acetic acid writhing test, respectively is probably due to an interference on the arachidonic acid (AA) metabolism. The most important antiinflammatory derivative 2-(2-formylfurane)pyridylhydrazone 5p presented a 79% inhibition of pleurisy at a dose of 80.1 mu mol/kg. We also described the results concerning the mechanism of action of this series of N-heterocyclic derivatives in platelet aggregation which suggest a Ca2+ participation, probably by a complexation scavenger mechanism. Compound 2-(2-formylfurane)pyridylhydrazone 5p was able to complex Ca2+ in in vitro experiments at 100 mu M concentration, indicating that this series of compounds can act as Ca2+ scavenger depending on the nature of the aryl moiety present at the imine subunit. (C) Elsevier, Paris.

  DOI：

  10.1016/s0223-5234(98)80008-1

文献信息

• Manganese‐Catalyzed Carbonylative Annulations for Redox‐Neutral Late‐Stage Diversification
  作者：Yu‐Feng Liang、Ralf Steinbock、Annika Münch、Dietmar Stalke、Lutz Ackermann

  DOI：10.1002/anie.201801111

  日期：2018.5.4

  inexpensive, nontoxic manganese catalyst enabled unprecedented redox‐neutral carbonylative annulations under ambient pressure. The manganese catalyst outperformed all other typically used base and precious‐metal catalysts. The outstanding versatility of the manganese catalysis manifold was reflected by ample substrate scope, setting the stage for effective late‐stage manipulations under racemization‐free

  廉价，无毒的锰催化剂可在环境压力下实现前所未有的氧化还原中性羰基环化反应。锰催化剂的性能优于所有其他常用的碱金属和贵金属催化剂。充足的底物范围反映了锰催化歧管出色的多功能性，为在无消旋条件下对许多市售药物和天然产物（包括生物碱，氨基酸，类固醇和碳水化合物）进行有效的后期操作奠定了基础。
• Regeneration of Aryl Ketones by Oxidative Cleavage of Pyridyl Hydrazones Mediated by Koser’s Reagent
  作者：Monika Sihag、Rinku Soni、Neha Rani、Mayank Kinger、Deepak Kumar Aneja

  DOI：10.2174/1570178620666230209145324

  日期：2023.8

  [Hydroxy(tosyloxy)iodo]benzene mediated the oxidative cleavage of pyridyl hydrazones to regenerate aryl ketones efficiently. Reaction occurred by simply stirring the hydrazone with hypervalent iodine reagent in dichloromethane at room temperature, where aryl ketones are produced up to 90% yield.

  [羟基（甲苯磺酰氧基）碘]苯介导吡啶基腙的氧化裂解以有效地再生芳基酮。在室温下，通过在二氯甲烷中简单搅拌腙和高价碘试剂即可发生反应，芳基酮的产率高达 90%。
• 10.1021/jacs.4c04623
  作者：Huang, Fan-Rui、Yao, Qi-Jun、Zhang, Peng、Teng, Ming-Ya、Chen, Jia-Hao、Jiang, Lu-Chen、Shi, Bing-Feng

  DOI：10.1021/jacs.4c04623

  日期：——

  offer straightforward access to a wide range of chiral molecules bearing [2.2.1]-bridged bicyclic cores with four and five consecutive stereocenters in a single step. Two elaborate salicyloxazoline (Salox) ligands were synthesized based on the rational design and mechanistic understanding. The well-defined chiral pockets generated from asymmetric coordination around the trivalent cobalt catalyst direct

  由于应变双环结构的多重反应性，通过不对称 C-H 活化选择性合成手性桥（杂）双环支架构成了巨大的挑战。在此，我们通过前所未有的钴催化对映选择性 C-H 活化/对称双环烯烃的亲核 [3 + 2] 成环来开发多米诺骨牌变换。该方法可以在一步中直接获得具有[2.2.1]桥联双环核心（具有四个和五个连续立构中心）的各种手性分子。基于合理设计和机理理解，合成了两种精心设计的水杨基恶唑啉（Salox）配体。三价钴催化剂周围的不对称配位产生的明确的手性口袋引导双环烯烃的方向，从而产生优异的对映选择性。
• Cyclopalladation compounds of the 2-pyridylhydrazone derivatives of p-substituted acetophenones and acetylthiophenes
  作者：Matsuo Nonoyama、Chisato Sugiura

  DOI：10.1016/s0277-5387(00)80982-1

  日期：1982.1
• Synthesis and evaluation of analgesic, antiinflammatory and antiplatelet properties of new 2-pyridylarylhydrazone derivatives
  作者：Adriane R. Todeschini、Ana Luisa P. de Miranda、Kelly Christine M. da Silva、Sergio C. Parrini、Eliezer J. Barreiro

  DOI：10.1016/s0223-5234(98)80008-1

  日期：1998.3

  This work describes recent results from our research program aiming at the synthesis and pharmacological evaluation of new compounds acting as antiinflammatory, analgesic and platelet antiaggregatory. In this paper the synthesis and the pharmacological profile as analgesic, antiinflammatory and anti-platelet of new functionalized 2-pyridylarylhydrazone derivatives 5a-r are discussed. This class of N-heterocyclic derivatives represents a new series of prototype candidates with analgesic and antiinflammatory properties possessing also an important anti-aggregating activity. The pharmacological results herein disclosed suggest that the antiinflammatory and analgesic activities of these new pyridynehydrazone derivatives observed in the carrageenan pleurisy model and acetic acid writhing test, respectively is probably due to an interference on the arachidonic acid (AA) metabolism. The most important antiinflammatory derivative 2-(2-formylfurane)pyridylhydrazone 5p presented a 79% inhibition of pleurisy at a dose of 80.1 mu mol/kg. We also described the results concerning the mechanism of action of this series of N-heterocyclic derivatives in platelet aggregation which suggest a Ca2+ participation, probably by a complexation scavenger mechanism. Compound 2-(2-formylfurane)pyridylhydrazone 5p was able to complex Ca2+ in in vitro experiments at 100 mu M concentration, indicating that this series of compounds can act as Ca2+ scavenger depending on the nature of the aryl moiety present at the imine subunit. (C) Elsevier, Paris.