3-oxo-2-(phenylhydrazono)-3-(2-thienyl)propanal

• 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-oxo-2-(phenylhydrazono)-3-(2-thienyl)propanal
• 英文别名: 3-oxo-2-(phenylhydrazinylidene)-3-thiophen-2-ylpropanal
• 化学式: C₁₃H₁₀N₂O₂S
• 分子量: 258.301
• InChiKey: NXYDNXYTPGXDLJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  18.0
• 可旋转键数：
  5.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  58.53
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  3-oxo-2-(phenylhydrazono)-3-(2-thienyl)propanal 在 sodium acetate 作用下， 以 甲醇 、 乙腈 为溶剂， 反应 72.0h， 生成
  参考文献：
  名称：

  通过分子内N–N键的形成合成2-取代的1,2,3-三唑

  摘要：

  分子内ñ - ñ键的形成导致基于分子内的各种2-芳基-1,2,3-三唑ñ - ñ键的形成进行说明。该反应可能遵循分子内S N 2置换机制，三甲基铵部分是分子内N - N键形成的良好离去基团。

  DOI：

  10.1002/ejoc.201901519
• 作为产物：
  描述：

  苯胺 、 (E)-3-二甲基氨基-1-噻吩-2-丙酮 在 盐酸 、 sodium nitrite 作用下， 以 水 为溶剂， 生成 3-oxo-2-(phenylhydrazono)-3-(2-thienyl)propanal
  参考文献：
  名称：

  Reactions under Pressure: Synthesis of Functionally Substituted Arylhydrazonal Derivatives as Precursors of Novel Pyridazines and Nicotinates

  摘要：

  Q-tube assisted multicomponent synthesis of novel arylhydrazonals, pyridazines and nicotinates has been explored. The target molecules have been prepared via one pot reaction of arylhydrazonals with activated methylene nitriles in either ethanolic piperidine, dimethyl acetylene dicarboxylate (DMAD), 1,4-diazobicyclo[2.2.2]octane (DABCO), or Ph3P under pressure. Such conditions make reaction time much shorter and yields higher as compared with those conducted under conventional conditions. The structures of products have been determined by X-ray crystallography and spectroscopic methods.

  DOI：

  10.1134/s1070363220040234

文献信息

• Efficient synthesis of 3-aroylcinnolines from aryl methyl ketones
  作者：Nouria A Al-Awadi、Mohamed Hilmy Elnagdi、Yehia A Ibrahim、Kamini Kaul、Ajith Kumar

  DOI：10.1016/s0040-4020(00)01141-8

  日期：2001.2

  An efficient synthesis of 3-aroylcinnolines starting from the appropriate aryl methyl ketones is described. The latter were converted in two steps to the corresponding 3-oxo-3-aryl-2-arylhydrazonopropanals, which upon acid catalyzed cyclization in conc. sulfuric acid or polyphosphoric acid (PPA) led to the corresponding 3-aroylcinnolines.

  描述了从合适的芳基甲基酮开始的3-芳基肉桂啉的有效合成。将后者分两步转化为相应的3-氧代-3-芳基-2-芳基肼基丙醛，其在浓盐酸中经酸催化环化。硫酸或多磷酸（PPA）生成相应的3-aroylcinnolines。
• Scope and Limitations of a Novel Synthesis of 3-Arylazonicotinates
  作者：Omniya Sayed Zaky、Moustafa Sherief Moustafa、Maghraby Ali Selim、Awatef Mohamed El-Maghraby、Mohamed Hilmy Elnagdi

  DOI：10.3390/molecules17055924

  日期：——

  The reaction of 3-oxo-3-phenyl-2-phenylhydrazonal with functionally substituted and heteroaromatic substituted acetonitrile to yield arylazonicotinic acid derivatives and 5-arylsubstituted pyridines was established. In some cases the produced nicotinates could not be isolated as they underwent thermally induced 6π-electrocyclization yielding polynuclear pyridine derivatives.

  3-氧-3-苯基-2-苯基肼酮与功能性取代和杂环取代的乙腈反应，生成芳基偶氮尼古丁酸衍生物和5-芳基取代的吡啶。在某些情况下，所产生的尼古丁酸酯无法被分离，因为它们经历了热诱导的6π-电环化反应，生成多核吡啶衍生物。
• Reassignment of the structures of condensation products of α-keto α′-formylarylhydrazones with ethyl cyanoacetate: a novel route to ethyl 5-arylazo-2-hydroxynicotinates
  作者：Saleh M. Al-Mousawi、Moustafa Sherief Moustafa、Ismail Abdelshafy Abdelhamid、Mohamed Hilmy Elnagdi

  DOI：10.1016/j.tetlet.2010.10.127

  日期：2011.1

  The condensation of α-keto α′-formylarylhydrazones with ethyl cyanoacetate afforded ethyl 5-arylazo-2-hydroxy-6-aryl (or alkyl) nicotinates. The structures of the reaction products could be established based on X-ray crystal structure determination.

  α-酮α'-甲酰基芳基hydr与氰基乙酸乙酯缩合，得到5-芳基偶氮-2-羟基-6-芳基（或烷基）烟酸酯。反应产物的结构可以基于X射线晶体结构的确定来建立。
• An efficient ultrasonic-mediated one-pot synthesis of 2,3,6,7,9-pentaazabicyclo[3.3.1]nonanes via a N,N-dimethylformamide dimethylacetal catalyzed Mannich-like reaction
  作者：Haider Behbehani、Hamada Mohamed Ibrahim

  DOI：10.1039/c6ra09210a

  日期：——

  A novel and straightforward method for one-pot synthesis of functionalized 2,3,6,7,9-pentaazabicyclo[3.3.1]nonane derivatives has been developed. The process, which involves ultrasonic irradiation promoted Mannich reaction between 3-oxo-2-arylhydrazonopropanals and ammonia in acetic acid, is catalyzed by N,N-dimethylformamide dimethylacetal (DMF-DMA) and generates the target products in 80–93% yields

  已经开发了一种新颖且直接的方法，用于一锅合成功能化的2,3,6,7,9-五氮杂双环[3.3.1]壬烷衍生物。N，N-二甲基甲酰胺二甲基乙缩醛（DMF-DMA）催化该过程，该过程涉及超声波辐照促进3-氧代-2-芳基肼基丙醛与氨在乙酸中的曼尼希反应，并以80-93％的产率生成目标产物。
• High-Pressure Metal-Free Catalyzed One-Pot Two-Component Synthetic Approach for New 5-Arylazopyrazolo[3,4-b]Pyridine Derivatives
  作者：AbdElAziz A. Nayl、Hamada Mohamed Ibrahim、Kamal M. Dawood、Wael A. A. Arafa、Ahmed I. Abd-Elhamid、Ismail M. Ahmed、Mohamed A. Abdelgawad、Hazim M. Ali、Ibrahim Hotan Alsohaimi、Ashraf A. Aly、Stefan Bräse、Asmaa Kamal Mourad

  DOI：10.3390/molecules27196369

  日期：——

  An appropriate and efficient Q-tube-assisted ammonium acetate-mediated protocol for the assembly of the hitherto unreported 5-arylazopyrazolo[3,4-b]pyridines was demonstrated. This methodology comprises the cyclocondensation reaction of 5-amino-2-phenyl-4H-pyrazol-3-one with an assortment of arylhydrazonals in an NH4OAc/AcOH buffer solution operating a Q-tube reactor. This versatile protocol exhibited

  证明了一种合适且有效的 Q 管辅助乙酸铵介导的方案，用于组装迄今为止未报道的 5-芳基吡唑并[3,4- b ] 吡啶。该方法包括 5-氨基-2-苯基-4 H-吡唑-3-酮与各种芳基腙醛在 NH 4中的环缩合反应操作 Q 管反应器的 OAc/AcOH 缓冲溶液。这种多功能协议具有几个突出的优点：易于处理、条件温和、可扩展、底物范围广、安全（Q-tube 套件仅用于压制和密封）和高原子经济性。因此，与常规条件相比，在高压下进行此类反应并利用 Q 管反应器似乎更适合获得所需的产品。应用多种光谱方法和 X 射线单晶技术来确认目标化合物的拟议结构。