2-(2-(4-chlorophenyl)hydrazono)-3-oxo-3-phenylpropanal | 40640-21-9

• 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: 2-(2-(4-chlorophenyl)hydrazono)-3-oxo-3-phenylpropanal
• 英文别名: 2-(2-p-chlorophenylhydrazono)-3-oxo-3-phenylpropanal；2-[(4-chlorophenyl)hydrazinylidene]-3-oxo-3-phenylpropanal
• CAS: 40640-21-9
• 化学式: C₁₅H₁₁ClN₂O₂
• 分子量: 286.718
• InChiKey: VFHDKINGQVZGSH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.19
• 重原子数：
  20.0
• 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：
  4.0

反应信息

• 作为反应物：
  描述：

  2-(2-(4-chlorophenyl)hydrazono)-3-oxo-3-phenylpropanal 在 ammonium acetate 、 三乙胺 作用下， 以 乙醇 为溶剂， 反应 0.07h， 以89%的产率得到4,8-di(benzoyl)-2,6-di(4-chlorophenyl)-2,3,6,7,9-pentaazabicyclo[3.3.1]nona-3,7-diene
  参考文献：
  名称：

  Facile Assembling of Novel 2,3,6,7,9-pentaazabicyclo- [3.3.1]nona-3,7-diene Derivatives under Microwave and Ultrasound Platforms

  摘要：

  一系列3-氧代-2-芳基肼酮丙醛衍生物与两摩尔比的醋酸铵反应，在三乙胺催化下，在乙醇溶剂中经过热、超声波和微波辐射三种不同的加热模式，得到了一系列四取代的2,3,6,7,9-五氮杂双环[3.3.1]壬-3,7-二烯衍生物，产率良好至优秀。通过光谱分析、分析数据以及选择性样品的X射线单晶数据，对所得产物的结构进行了全面表征。

  DOI：

  10.3390/molecules24061110
• 作为产物：
  描述：

  2-p-chlorophenylhydrazono-1-phenylethanone 在 硝基苯 作用下， 以 甲醇 、 水 为溶剂， 反应 4.0h， 生成 2-(2-(4-chlorophenyl)hydrazono)-3-oxo-3-phenylpropanal
  参考文献：
  名称：

  2-芳基肼基-3-羟基-1-丙酮的改进合成及其在有效合成哒嗪衍生物中的应用

  摘要：

  在蒙脱石 K10 存在下或通过在甲醇和 TEA 中简单搅拌，2-芳基腙-1-苯基乙酮 2a-c 与甲醛的反应导致选择性合成 2-芳基腙-3-羟基-1-苯基丙-1-酮衍生物 3a-c高产。在 DPE/DABCO 中使用微波辐射在 DPE/DABCO 中加热 1a 5 分钟，得到 73% 的吡咯并[3,4-c]哒嗪 8。化合物 2a-c 与亚苄基丙二腈 9a 或 2-氰基肉桂酸乙酯反应9b 在回流的乙醇和哌啶或 -壳聚糖中生成新的哒嗪衍生物 10a-f，在醋酸/盐酸混合物中回流时，这些衍生物转化为哒嗪酮 11a-c。

  DOI：

  10.3998/ark.5550190.0012.225

文献信息

• Tandem one-pot synthesis of 2-arylcinnolin-6-one derivatives from arylhydrazonopropanals and acetoacetanilides using sustainable ultrasound and microwave platforms
  作者：Hamad M. Al-Matar、Kamal M. Dawood、Wael M. Tohamy

  DOI：10.1039/c8ra06494f

  日期：——

  Several 2-arylcinnolin-6(2H)-one derivatives were synthesizedviatandem annulation of a large number of 3-oxo-2-arylhydrazonopropanals with acetoacetanilide under three different heating modes.

  在三种不同的加热模式下，大量 3-oxo-2-arylhydrazonopropanals 与乙酰乙酰苯胺串联环化，合成了多种 2-芳基噌啉-6(2H)-酮衍生物。
• Synthesis of A New Class of Pyridazin-3-one and 2-Amino-5-arylazopyridine Derivatives and Their Utility in the Synthesis of Fused Azines
  作者：Hamada Ibrahim、Haider Behbehani

  DOI：10.3390/molecules19022637

  日期：——

  A general route for the synthesis of a novel class of pyridazin-3-one derivatives 3 by the reaction in acetic anhydride between 3-oxo-2-arylhydrazonopropanals 1 and some active methylene compounds like p-nitrophenylacetic acid and cyanoacetic acid was established. Under these conditions the pyridazin-3-one derivatives 3 were formed as the sole isolable products in excellent yield. The 6-acetyl-3-oxopyridazine derivative 3l was reacted with DMF-DMA to afford the corresponding enaminone derivative 4, which reacts with a variety of aminoazoles to afford the corresponding azolo[1,5-a]pyrimidine derivatives 5–7. Also, in order to explore the viability and generality of a recently uncovered reaction between 3-oxo-2-arylhydrazonopropanals and active methylene compounds, a variety of 2-amino-6-aryl-5-arylazo-3-aroylpyridines 16–19 were prepared by reacting 3-oxo-2-arylhydrazonopropanals with miscellaneous active methylene compounds like 3-oxo-3-phenylpropionitrile, hetaroylacetonitriles and cyanoacetamides. These 2-aminopyridine derivatives undergo smooth reactions with cyanoacetic acid that led to the formation in high yield of a new class of 1,8-naphthyridine derivatives 24. The structures of all new substances prepared in this investigation were determined by the different analytical spectroscopic methods, in addition to the X-ray crystallographic analysis.

  通过在醋酸酐中将3-氧-2-芳基腙丙醛1与一些活性亚甲基化合物（如对硝基苯乙酸和氰基乙酸）反应，建立了一种合成新型吡嗪-3-酮衍生物3的通用路线。在这些条件下，吡嗪-3-酮衍生物3作为唯一可分离的产物，以优异的产率形成。6-乙酰-3-氧吡嗪衍生物3l与DMF-DMA反应，生成相应的烯胺酮衍生物4，后者与多种氨基杂环化合物反应，形成相应的杂氮[1,5-a]吡啶衍生物5–7。此外，为了探讨近期发现的3-氧-2-芳基腙丙醛与活性亚甲基化合物之间反应的可行性和普遍性，通过将3-氧-2-芳基腙丙醛与多种活性亚甲基化合物（如3-氧-3-苯丙腈、杂芳基丙酮腈和氰基乙酰胺）反应，合成了一系列2-氨基-6-芳基-5-芳基氮杂-3-芳酰吡啶衍生物16–19。这些2-氨基吡啶衍生物与氰基乙酸发生顺利反应，导致新一类1,8-萘啶衍生物24的高产率形成。本研究中制备的所有新物质的结构均通过不同的分析光谱方法确定，此外还进行了X射线晶体分析。
• 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。
• Syntheses of novel disperse dyes based on arylazophenols: Synthesis, characterizations and applications
  作者：Morsy Ahmed El-Apasery、Mahmoud Elsayed Ahmed Abdellatif、Fathy Ahmed Yassin、Sara Morsy Ahmed

  DOI：10.4314/bcse.v37i4.15

  日期：——

  ABSTRACT. Three compounds, phenyl propenone, p-tolyl propenone, and bromo phenylpropenone derivatives 3a-c were produced in good yields via condensation derivatives of acetophenone with dimethyl formamide dimethyl acetal (DMFDMA) in presence of xylene as a solvent. Compounds 5a-f were produced by coupling the enaminones 3a-c with diazonium chloride 4a or 4b. Compounds 5a-f were reacted with acetone to create novel disperse dyes 9a-f. Mass spectra, (FT-IR), elemental analysis, and 1H-NMR spectra were used to confirm the chemical structure of the new dyes. The new disperse  dyes were used in dyeing polyester fabrics at low temperature, and fabrics with colors ranging from yellowish brown to dark yellowish brown were obtained. Thus, the different fastness properties of these dyed fabrics were studied, which gave excellent results. Finally, the biological activity of these new dyes was studied, which showed that they have biological activity against bacteria and fungi.   KEY WORDS: Azo dye, Carrier, Low temperature dyeing, Arylazophenols, Color fastness Bull. Chem. Soc. Ethiop. 2023, 37(4), 993-1002.                                                              DOI: https://dx.doi.org/10.4314/bcse.v37i4.15                                                      

  摘要在二甲苯作为溶剂的情况下，通过苯乙酮与二甲基甲酰胺二甲基缩醛（DMFDMA）的缩合衍生物，制得了三种化合物，即苯基丙烯酮、对甲苯基丙烯酮和溴代苯基丙烯酮衍生物 3a-c，收率良好。烯酮 3a-c 与重氮氯化物 4a 或 4b 偶联生成化合物 5a-f。化合物 5a-f 与丙酮反应生成新型分散染料 9a-f。质谱、（傅立叶变换红外光谱）、元素分析和 1H-NMR 光谱用于确认新染料的化学结构。将新型分散染料用于涤纶织物的低温染色，得到的织物颜色从黄棕色到深黄棕色不等。因此，对这些染色织物的不同牢度特性进行了研究，结果非常理想。最后，研究了这些新型染料的生物活性，结果表明它们对细菌和真菌具有生物活性； ； 关键词：偶氮染料、载体、低温染色、芳基偶氮苯酚、色牢度 ； Bull.Chem.Soc.2023，37（4），993-1002； DOI: https://dx.doi.org/10.4314/bcse.v37i4.15
• Microwave-assisted chemoselective synthesis and photophysical properties of 2-arylazo-biphenyl-4-carboxamides from hydrazonals
  作者：Abdulrahman M. Alazemi、Kamal M. Dawood、Hamad M. Al-Matar、Wael M. Tohamy

  DOI：10.1039/d3ra04558g

  日期：——

  were characterized by several spectroscopic techniques including IR, 1H- and 13C-NMR, MS and HRMS, and X-ray single crystals of three examples. The photophysical properties of the new products were also evaluated, with a particular focus on their absorption and emission spectra, which provided valuable information regarding their optical properties. The new compounds emitted 513–549 nm green fluorescence

  3-氧代-2-芳基亚肼基丙醛与乙酰乙酰苯胺以等摩尔比在DBU/1,4-二恶烷/微波辐射反应条件下反应，导致化学选择性形成4-芳基偶氮-5-羟基-苯甲酰胺衍生物。所获得的联苯-4-甲酰胺的结构通过多种光谱技术进行了表征，包括IR、 1 H-和13 C-NMR、MS和HRMS，以及三个实施例的X射线单晶。还评估了新产品的光物理性质，特别关注其吸收和发射光谱，这提供了有关其光学性质的宝贵信息。新化合物在丙酮溶液中在紫外线照射下发出 513-549 nm 的绿色荧光。