2,2'-(naphthalene-2,7-diylbis(oxy))diacetohydrazide | 817159-08-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2,2'-(naphthalene-2,7-diylbis(oxy))diacetohydrazide
• 英文别名: 2-[7-(2-Hydrazinyl-2-oxoethoxy)naphthalen-2-yl]oxyacetohydrazide；2-[7-(2-hydrazinyl-2-oxoethoxy)naphthalen-2-yl]oxyacetohydrazide
• CAS: 817159-08-3
• 化学式: C₁₄H₁₆N₄O₄
• 分子量: 304.305
• InChiKey: IXJPJXDTWCNWBH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  22
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  129
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  alpha-酮戊二酸 、 2,2'-(naphthalene-2,7-diylbis(oxy))diacetohydrazide 以 二甲基亚砜 为溶剂， 反应 2.0h， 生成
  参考文献：
  名称：

  Screening of π-Basic Naphthalene and Anthracene Amplifiers for π-Acidic Synthetic Pore Sensors

  摘要：

  Synthetic ion channels and pores attract current attention as multicomponent sensors in complex matrixes. This application requires the availability of reactive signal amplifiers that covalently capture analytes and drag them into the pore. pi-Basic 1,5-dialkoxynaphthalenes (1,5-DAN) are attractive amplifiers because aromatic electron donor-acceptor (AEDA) interactions account for their recognition within pi-acidic naphthalenediimide (NDI) rich synthetic pores. Focusing on amplifier design, we report here the synthesis of a complete collection of DAN and dialkoxyanthracene amplifiers, determine their oxidation potentials by cyclic voltammetry, and calculate their quadrupole moments. Blockage experiments reveal that subtle structural changes in regioisomeric DAN amplifiers can be registered within NDI pores. Frontier orbital overlap in AEDA complexes, oxidation potentials, and, to a lesser extent, quadrupole moments are shown to contribute to isomer recognition by synthetic pores. Particularly important with regard to practical applications of synthetic pores as multianalyte sensors, we further demonstrate that application of the lessons learned with DAN regioisomers to the expansion to dialkoxyanthracenes provides access to privileged amplifiers with submicromolar activity.

  DOI：

  10.1021/ja078256t
• 作为产物：
  描述：

  2,7-二羟基萘 在 potassium carbonate 、 一水合肼 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 22.0h， 生成 2,2'-(naphthalene-2,7-diylbis(oxy))diacetohydrazide
  参考文献：
  名称：

  Microwave-assisted synthesis and evaluation of antibacterial activity of 2,2'-(naph- thalene-2,7-diylbis(oxy))bis(N'-substituted acetohydrazide) derivatives

  摘要：

  已经合成了一系列Schiff碱，名为2,2'-(萘-2,7-二基(氧))双(N'-取代乙酰肼)衍生物(4a-m)，通过酸催化的反应，将芳香/杂环芳香醛与2,2'-(萘-2,7-二基(氧))二乙酰肼(3)在微波辐射和常规方法下进行缩合。所有新合成化合物的结构已通过红外光谱、1H NMR、13C NMR和质谱进行了表征。所有合成的化合物均已筛选其体外抗菌活性。

  DOI：

  10.4314/bcse.v26i2.9

文献信息

• Ultrasound-assisted synthesis of 2,5-dimethyl-N-substituted pyrroles catalyzed by uranyl nitrate hexahydrate
  作者：V.S.V. Satyanarayana、A. Sivakumar

  DOI：10.1016/j.ultsonch.2011.02.007

  日期：2011.9

  An efficient synthesis of different novel 2,5-dimethyl-N-substituted pyrrole derivatives by the Paal-Knorr condensation has been accomplished using uranyl nitrate hexahydrate as catalyst under soft conditions and ultrasonic irradiation. The synthesized compounds were confirmed through spectral characterization using IR, (1)H NMR, (13)C NMR and mass spectra.

  使用六水合铀酰硝酸铀酯在柔软条件下和超声辐射下，通过Paal-Knorr缩合反应成功合成了不同的新型2,5-二甲基-N-取代的吡咯衍生物。通过使用IR，（1）H NMR，（13）C NMR和质谱的光谱表征来确认合成的化合物。
• Ultrasonic Assisted Synthesis of Naphthalene Substituted Schiff Base Derivatives and Their Antioxidant Activity Studies
  作者：K. Venkatesan、V. S. V. Satyanarayana、A. Sivakumar

  DOI：10.1002/jccs.201190091

  日期：2011.9

  aryl/hetero aromatic aldehydes with 2,2′‐ [naphthalene‐2,7‐diylbis(oxy)]diacetohydrazide (3) under reflux temperature and ultrasonic irradiation. These Schiff base derivatives were confirmed through spectral characterization using IR, 1H NMR, 13C NMR and mass spectra. All the synthesized compounds were screened for their antioxidant activity using DPPH free radical scavenging method.

  通过芳基/杂芳族醛与2的酸催化缩合反应合成了新的席夫碱衍生物2,2'-[萘-2,7-二基双（氧基）]双[N'-取代的乙酰肼]（4a-m）回流温度和超声辐射下，2'-[萘-2,7-二基双（氧基）]二乙酰肼（3）。这些席夫碱衍生物通过使用IR，1 H NMR，13 C NMR和质谱的光谱表征来确认。使用DPPH自由基清除方法筛选所有合成的化合物的抗氧化活性。
• Screening of π-Basic Naphthalene and Anthracene Amplifiers for π-Acidic Synthetic Pore Sensors
  作者：Shinya Hagihara、Ludovic Gremaud、Guillaume Bollot、Jiri Mareda、Stefan Matile

  DOI：10.1021/ja078256t

  日期：2008.4.1

  Synthetic ion channels and pores attract current attention as multicomponent sensors in complex matrixes. This application requires the availability of reactive signal amplifiers that covalently capture analytes and drag them into the pore. pi-Basic 1,5-dialkoxynaphthalenes (1,5-DAN) are attractive amplifiers because aromatic electron donor-acceptor (AEDA) interactions account for their recognition within pi-acidic naphthalenediimide (NDI) rich synthetic pores. Focusing on amplifier design, we report here the synthesis of a complete collection of DAN and dialkoxyanthracene amplifiers, determine their oxidation potentials by cyclic voltammetry, and calculate their quadrupole moments. Blockage experiments reveal that subtle structural changes in regioisomeric DAN amplifiers can be registered within NDI pores. Frontier orbital overlap in AEDA complexes, oxidation potentials, and, to a lesser extent, quadrupole moments are shown to contribute to isomer recognition by synthetic pores. Particularly important with regard to practical applications of synthetic pores as multianalyte sensors, we further demonstrate that application of the lessons learned with DAN regioisomers to the expansion to dialkoxyanthracenes provides access to privileged amplifiers with submicromolar activity.
• Microwave-assisted synthesis and evaluation of antibacterial activity of 2,2'-(naph- thalene-2,7-diylbis(oxy))bis(N'-substituted acetohydrazide) derivatives
  作者：K. Venkatesan、V.S.V. Satyanarayana、A. Sivakumar

  DOI：10.4314/bcse.v26i2.9

  日期：——

  A series of Schiff base of 2,2'-(naphthalene-2,7-diylbis(oxy))bis(N'-substituted acetohydrazide) (4a-m) derivatives has been synthesized by the acid catalyzed condensation of aryl/hetero aromatic aldehydes with 2,2'-(naphthalene-2,7-diylbis(oxy))diacetohydrazide (3) under microwave irradiation and conventional method for comparison. The structures of all the newly synthesized compounds have been characterized by IR, 1H NMR, 13C NMR and Mass spectra. All the synthesized compounds have been screened for their in vitro antibacterial activity.

  已经合成了一系列Schiff碱，名为2,2'-(萘-2,7-二基(氧))双(N'-取代乙酰肼)衍生物(4a-m)，通过酸催化的反应，将芳香/杂环芳香醛与2,2'-(萘-2,7-二基(氧))二乙酰肼(3)在微波辐射和常规方法下进行缩合。所有新合成化合物的结构已通过红外光谱、1H NMR、13C NMR和质谱进行了表征。所有合成的化合物均已筛选其体外抗菌活性。