3-pyridinecarboxaldehyde phenylhydrazone | 57023-37-7

• 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-pyridinecarboxaldehyde phenylhydrazone
• 英文别名: pyridine-3-carbaldehyde phenylhydrazone；3-Pyridinecarbaldehyde phenylhydrazone；3-pyridinaldehyde-phenylhydrazone；N-(pyridin-3-ylmethylideneamino)aniline
• CAS: 57023-37-7
• 化学式: C₁₂H₁₁N₃
• 分子量: 197.239
• InChiKey: NHYWOFCMLOALEI-UHFFFAOYSA-N

物化性质

• 熔点：
  159 °C
• 沸点：
  351.6±24.0 °C(Predicted)
• 密度：
  1.07±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-pyridinecarboxaldehyde phenylhydrazone 在 potassium trimethylsilonate 作用下， 以 四氢呋喃 为溶剂， 反应 16.0h， 以63%的产率得到potassium nicotinate
  参考文献：
  名称：

  三甲硅烷醇酸酯催化裂解Hy的有效方法氧化芳香醛

  摘要：

  芳香醛可被有效地氧化成相应的羧酸。该方案在一锅中涉及两个反应步骤。首先，通过与苯肼反应将醛转化为，然后用三甲基硅烷醇化物处理以产生羧酸。氧化既可以在溶液中也可以在固体载体上进行。

  DOI：

  10.1002/ejoc.201601238
• 作为产物：
  描述：

  3-吡啶甲醛 在 苯肼 作用下， 以 乙醇 为溶剂， 生成 3-pyridinecarboxaldehyde phenylhydrazone
  参考文献：
  名称：

  Certain fungicidal pyridinecarbaldehyde phenylhydrazones

  摘要：

  某些吡啶甲醛苯肼，用作杀真菌剂。

  公开号：

  US04212868A1

文献信息

• Process for producing hydrazone derivatives of pyridinaldehydes
  申请人：Ciba-Geigy Corporation

  公开号：US04237275A1

  公开（公告）日：1980-12-02

  An improved process for producing pyridinaldehydes and hydrazone derivatives thereof, for example, pyridinaldehyde-phenylhydrazones, is described. This comprises reacting a aminomethylpyridine with an aldehyde or a ketone to give a compound of the formula ##STR1## isomerizing the compound (III), in the presence of suitable catalysts, to a compound of the formula ##STR2## and converting the compound (V), in the presence of an acid and optionally in the presence of a hydrazine, into a pyridinaldehyde or a pyridinaldehyde-hydrazone. It is possible to produce by the process according to the invention pyridinaldehydes and pyridinaldehyde-hydrazones in a simple manner, under mild ecologically favorable conditions and in good to very good yields.

  描述了一种改进的生产吡啶醛和其酰肼衍生物（例如，吡啶醛苯基酰肼）的方法。该方法包括将氨基甲基吡啶与醛或酮反应，得到一个具有以下结构的化合物：##STR1##，在适当催化剂的存在下，将化合物（III）异构化为具有以下结构的化合物：##STR2##，然后在酸的存在下，可选地在存在有肼的情况下，将化合物（V）转化为吡啶醛或吡啶醛酰肼。根据本发明的方法可以简单地在温和的生态有利条件下并且产率良好至非常良好地生产吡啶醛和吡啶醛酰肼。
• Copper-Catalyzed Transformation of Hydrazones into Halogenated Azabutadienes, Versatile Building Blocks for Organic Synthesis
  作者：Valentine G. Nenajdenko、Alexey V. Shastin、Vladimir M. Gorbachev、Sergey V. Shorunov、Vasiliy M. Muzalevskiy、Anna I. Lukianova、Pavel V. Dorovatovskii、Victor N. Khrustalev

  DOI：10.1021/acscatal.6b03196

  日期：2017.1.6

  A one-step copper-catalyzed reaction of aldehyde-derived N-substituted hydrazones with CCl4 resulted in efficient synthesis of 4,4-dichloro-1,2-diazabuta-1,3-dienes. It was proven that this C–C bond-forming cascade reaction operates via an addition of trichloromethyl radical to the C═N bond of hydrazone followed by a base-induced elimination of HCl. The reaction was found to be very general, as diverse

  醛衍生的N-取代的azo与CCl 4的一步铜催化反应可有效合成4,4-二氯-1,2-二氮杂丁-1,3-二烯。事实证明，这种C–C键形成级联反应是通过在的C═N键中添加三氯甲基自由基，然后通过碱诱导的HCl去除而实现的。发现该反应非常笼统，因为在N位具有各种芳族基团以及C位具有芳族，脂族和杂环取代基的各种azo是能够与多种多卤代化合物（CCl 3 Br，CBr 4，CCl 3 CN，CCl 3 COOEt，CCl 3 CF 3，CBr3 CF 3）来生产一族功能化的1,2-二氮杂丁-1,3-二烯。已证明，所制备的杂二烯是用于各种有价值的无环和杂环分子的直接组装的高度通用的构建基。
• Exceptionally rapid oxime and hydrazone formation promoted by catalytic amine buffers with low toxicity
  作者：Dennis Larsen、Anna M. Kietrys、Spencer A. Clark、Hyun Shin Park、Andreas Ekebergh、Eric T. Kool

  DOI：10.1039/c8sc01082j

  日期：——

  Hydrazone and oxime bond formation between α-nucleophiles (e.g. hydrazines, alkoxy-amines) and carbonyl compounds (aldehydes and ketones) is convenient and is widely applied in multiple fields of research. While the reactants are simple, a substantial drawback is the relatively slow reaction at neutral pH. Here we describe a novel molecular strategy for accelerating these reactions, using bifunctional

  在α-亲核试剂（例如肼，烷氧基胺）和羰基化合物（醛和酮）之间形成和肟键很方便，并广泛应用于多个研究领域。尽管反应物很简单，但是一个主要的缺点是在中性pH下反应较慢。在这里，我们描述了一种新型的分子策略，这些分子可以使用不仅控制pH值而且可以催化反应的双功能缓冲化合物来加速这些反应。缓冲液可以在pH 5–9（5–50 mM）下使用，并将反应加速几个数量级，从而产生> 10 M -1 s -1的二级速率常数。有效的双官能胺包括2-（氨基甲基）咪唑和N，N-二甲基乙二胺。与以前的二氨基苯催化剂不同，新的缓冲胺被发现对人体细胞毒性低，可用于促进细胞应用中的反应。
• Electrochemical Synthesis of Pyrazolines and Pyrazoles via [3+2] Dipolar Cycloaddition
  作者：Martin Linden、Silja Hofmann、Antonia Herman、Nicole Ehler、Robin M. Bär、Siegfried R. Waldvogel

  DOI：10.1002/anie.202214820

  日期：2023.2.20

  Electrochemically initiated [3 2] cycloaddition reactions of readily available and less toxic starting materials enable a facile synthesis of pyrazolines and pyrazoles. Application of a biphasic system and sodium iodide in a dual role as mediator and electrolyte allows for selective reactions with outstanding robustness towards scalability.

  电化学引发的 [3 2] 环加成反应容易获得且毒性较低的起始材料使吡唑啉和吡唑的合成变得容易。双相系统和碘化钠作为介质和电解质的双重作用的应用允许选择性反应对可扩展性具有出色的鲁棒性。
• Potent antimicrobial agents against azole-resistant fungi based on pyridinohydrazide and hydrazomethylpyridine structural motifs
  作者：Gregory L. Backes、Branko S. Jursic、Donna M. Neumann

  DOI：10.1016/j.bmc.2015.04.040

  日期：2015.7

  Schiff base derivatives have recently been shown to possess antimicrobial activity, and these derivatives include a limited number of salicylaldehyde hydrazones. To further explore this structure-activity relationship between salicylaldehyde hydrazones and antifungal activity, we previously synthesized and analyzed a large series of salicylaldehyde and formylpyridinetrione hydrazones for their ability to inhibit fungal growth of both azole-susceptible and azole-resistant species of Candida. While many of these analogs showed excellent growth inhibition with low mammalian cell toxicity, their activity did not extend to azole-resistant species of Candida. To further dissect the structural features necessary to inhibit azole-resistant fungal species, we synthesized a new class of modified salicylaldehyde derivatives and subsequently identified a series of modified pyridine-based hydrazones that had potent fungicidal antifungal activity against multiple Candida spp. Here we would like to present our synthetic procedures as well as the results from fungal growth inhibition assays, mammalian cell toxicity assays, time-kill assays and synergy studies of these novel pyridine-based hydrazones on both azole-susceptible and azole-resistant fungal species. (C) 2015 Elsevier Ltd. All rights reserved.