(Z)-N'-(furan-2-ylmethylene)isonicotinic hydrazide | 1356726-51-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: (Z)-N'-(furan-2-ylmethylene)isonicotinic hydrazide
• 英文别名: (Z)-N'-((furan-2-yl)methylene)isonicotinohydrazide；Furfural isonicotinoylhydrazone, (Z)-；N-[(Z)-furan-2-ylmethylideneamino]pyridine-4-carboxamide
• CAS: 1356726-51-6
• 化学式: C₁₁H₉N₃O₂
• 分子量: 215.211
• InChiKey: OOGABHAPRCRJSP-JYRVWZFOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  16
• 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：
  67.5
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (Z)-N'-(furan-2-ylmethylene)isonicotinic hydrazide 以 乙腈 为溶剂， 反应 2.08h， 生成 2-furaldehyde isonicotinoylhydrazone
  参考文献：
  名称：

  Acylhydrazones as Widely Tunable Photoswitches

  摘要：

  Molecular photoswitches have attracted much attention in biological and materials contexts. Despite the fact that existing classes of these highly interesting functional molecules have been heavily investigated and optimized, distinct obstacles and inherent limitations remain. Considerable synthetic efforts and complex structure property relationships render the development and exploitation of new photoswitch families difficult. Here, we focus our attention on acylhydrazones: a novel, yet underexploited class of photochromic molecules based on the imine structural motif. We optimized the synthesis of these potent photoswitches and prepared a library of over 40 compounds, bearing different substituents in all four crucial positions of the backbone fragment, and conducted a systematic study of their photochromic properties as a function of structural variation. This modular family of organic photoswitches offers a unique combination of properties and the compounds are easily prepared on large scales within hours, through an atom-economic synthesis, from commercially available starting materials. During our thorough spectroscopic investigations, we identified photoswitches covering a wide range of thermal half-lives of their (Z)-isomers, from short-lived T-type to thermally stable P-type derivatives. By proper substitution, excellent band separation between the absorbance maxima of (E)- and (Z)-isomers in the UV or visible region could be achieved. Our library furthermore includes notable examples of rare negative photochromic systems, and we show that acylhydrazones are highly fatigue resistant and exhibit good quantum yields.

  DOI：

  10.1021/jacs.5b09519
• 作为产物：
  描述：

  2-furaldehyde isonicotinoylhydrazone 以 乙腈 为溶剂， 反应 0.33h， 生成 (Z)-N'-(furan-2-ylmethylene)isonicotinic hydrazide
  参考文献：
  名称：

  Acylhydrazones as Widely Tunable Photoswitches

  摘要：

  Molecular photoswitches have attracted much attention in biological and materials contexts. Despite the fact that existing classes of these highly interesting functional molecules have been heavily investigated and optimized, distinct obstacles and inherent limitations remain. Considerable synthetic efforts and complex structure property relationships render the development and exploitation of new photoswitch families difficult. Here, we focus our attention on acylhydrazones: a novel, yet underexploited class of photochromic molecules based on the imine structural motif. We optimized the synthesis of these potent photoswitches and prepared a library of over 40 compounds, bearing different substituents in all four crucial positions of the backbone fragment, and conducted a systematic study of their photochromic properties as a function of structural variation. This modular family of organic photoswitches offers a unique combination of properties and the compounds are easily prepared on large scales within hours, through an atom-economic synthesis, from commercially available starting materials. During our thorough spectroscopic investigations, we identified photoswitches covering a wide range of thermal half-lives of their (Z)-isomers, from short-lived T-type to thermally stable P-type derivatives. By proper substitution, excellent band separation between the absorbance maxima of (E)- and (Z)-isomers in the UV or visible region could be achieved. Our library furthermore includes notable examples of rare negative photochromic systems, and we show that acylhydrazones are highly fatigue resistant and exhibit good quantum yields.

  DOI：

  10.1021/jacs.5b09519

文献信息

• Synthesis and Antimicrobial Activity of N-[2-(aryl/substituted aryl)-4-oxo-1,3-thiazolidin-3-yl]pyridine-4-carboxamide
  作者：Asha B. Thomas、Rabindra K. Nanda、Lata P. Kothapalli、Avinash D. Deshpande

  DOI：10.5012/jkcs.2011.55.6.960

  日期：2011.12.20

  A series of isonicotinyl hydrazones and their 4-thiazolidinones have been synthesized by condensation of isonicotinic acid hydrazide with various aromatic aldehydes to yield Schiff's bases, followed by the cyclocondensation of Schiff's bases with 2-mercaptoacetic acid to yield their 4-thiazolidinones. The synthesized compounds have been characterized by their elemental, analytical and spectral studies. All these compounds were evaluated for their invitro antimicrobial activity against a spectrum of non-resistant and resistant microbial organisms. These studies proved that compounds 5e,i against B. subtilis; 5e,f,h against B. anthracis; 5g,i against S. aureus showed good activity at lower concentrations. Compounds 5d-5i displayed significant activity against resistant strain of K. pneumonia with minimum inhibitory potency in the concentration range of 2-16 ug/ml.

  通过异烟酸酰肼与各种芳香醛缩合生成席夫碱，然后席夫碱与2-巯基乙酸环缩合生成4-噻唑烷酮，合成了一系列异烟酰腙及其4-噻唑烷酮。合成的化合物已通过元素、分析和光谱研究进行了表征。所有这些化合物都针对一系列非耐药和耐药微生物的体外抗菌活性进行了评估。这些研究证明化合物5e、i具有抗枯草芽孢杆菌的作用； 5e，f，h 对抗炭疽芽孢杆菌； 5g,i 在较低浓度下对金黄色葡萄球菌表现出良好的活性。化合物5d-5i对肺炎克雷伯菌耐药菌株表现出显着的活性，在2-16ug/ml的浓度范围内具有最小抑制效力。
• Investigating corrosion failure in N80 carbon Steel: Experimental and theoretical insights into isonicotinohydrazide derivatives as inhibitors in acidic conditions
  作者：Abdelkarim Ait Mansour、Karthick Subbiah、Hassane Lgaz、Mustafa R. Al-Hadeethi、Mouslim Messali、Taejoon Park、Lahcen Bazzi、Han-seung Lee、Rachid Salghi

  DOI：10.1016/j.inoche.2023.112007

  日期：2024.3

  This research work is a detailed analysis of the failure mechanisms related to the corrosion of N80 carbon steel (N80-CS) in an acidic environment (15 wt% HCl), commonly encountered in oil and gas industry pipelines. The study investigates the corrosion failure, focusing on the interactions with two isonicotinohydrazide derivatives, namely N'-[(Z)-furan-2-ylmethylidene]pyridine-4-carbohydrazide (FMI)

  这项研究工作详细分析了石油和天然气工业管道中常见的酸性环境（15 wt% HCl）中与 N80 碳钢（N80-CS）腐蚀相关的失效机制。该研究调查了腐蚀失效，重点关注与两种异烟酰肼衍生物的相互作用，即 N'-[(Z)-呋喃-2-基亚甲基]吡啶-4-碳酰肼 (FMI) 和 N'-[(Z)-苯基亚甲基]吡啶-4-碳酰肼（BIH）。实验和理论方法的结合，包括失重（WL）、电化学分析、场发射扫描电子显微镜（FE-SEM）、原子力显微镜（AFM）、密度泛函紧结合（DFTB）半经验计算、前沿分子利用轨道分析、Fukui 函数研究和分子动力学模拟来确定 N80-CS 的腐蚀和腐蚀抑制行为。实验结果表明，FMI 和 BIH 的抑制性能随这些抑制剂的浓度成比例增加，抑制效率分别为 95% 和 98%。这一性能体现在最佳浓度下极化电阻的增强和腐蚀电流密度的显着降低。此外，它们在长时间浸泡（长达 5 天）下表现