2-[(4-Methoxy-phenyl)-hydrazono]-3-oxo-3-phenyl-propionaldehyde | 40640-24-2

• 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-[(4-Methoxy-phenyl)-hydrazono]-3-oxo-3-phenyl-propionaldehyde
• 英文别名: 2-[(4-methoxyphenyl)hydrazinylidene]-3-oxo-3-phenylpropanal
• CAS: 40640-24-2
• 化学式: C₁₆H₁₄N₂O₃
• 分子量: 282.299
• InChiKey: NGERMRGKRPZCKJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.54
• 重原子数：
  21.0
• 可旋转键数：
  6.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  67.76
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  2-[(4-Methoxy-phenyl)-hydrazono]-3-oxo-3-phenyl-propionaldehyde 在 PPA 作用下， 反应 0.17h， 以35%的产率得到3-benzoyl-6-methoxycinnoline
  参考文献：
  名称：

  从芳基甲基酮高效合成3-芳基肉桂啉

  摘要：

  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。

  DOI：

  10.1016/s0040-4020(00)01141-8

文献信息

• 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。
• A strategy for the synthesis of 2-aryl-3-dimethylaminopyrazolo-[3,4-c]pyridines that utilizes [4+1] cycloaddition reactions of 5-arylazo-2,3,6-trisubstituted pyridines
  作者：Haider Behbehani、Hamada Mohamed Ibrahim

  DOI：10.1016/j.tet.2013.10.061

  日期：2013.12

  In order to explore the viability and generality of a recently uncovered [4+1] cycloaddition based strategy for the preparation of pyrazolo[3,4-c]pyridine derivatives, members of a series of 5-arylazo-2,3,6-trisubstituted pyridines were prepared by reactions of 3-oxo-2-arylhydrazonopropanals with 3-oxo-3-phenylpropionitrile. The results show that 3-oxo-3-phenylpropionitrile reacts with hydrazone substrates

  为了探讨最近发现的基于[4 + 1]环加成反应的吡唑并[3,4- c ]吡啶衍生物的制备方法的可行性和一般性，该策略是一系列5-芳基偶氮-2,3,6-的成员通过3-氧代-2-芳基肼基丙醛与3-氧代-3-苯基丙腈的反应制备三取代的吡啶。结果表明3-氧代-3-苯基丙腈与底物反应，该底物在芳基hydr部分的N-芳基环上不包含吸电子取代基，从而有效地产生6-芳基-2-苯基-5-芳基氮杂腈。相反，在3-氧代-2-芳基肼基丙醛的反应中生成2-氨基-6-芳基-5-芳基偶氮-3-苯甲酰基吡啶，其在N上含有吸电子取代基。-芳基部分。以预测的方式，6-芳基-2-苯基-5-芳基氮杂腈与二甲基甲酰胺二甲基乙缩醛（DMF-DMA）进行平滑反应，从而导致形成一类新的2-芳基-3-二甲基氨基吡唑并[3,4- c ]吡啶。此过程的机理涉及[4 + 1]环加成反应，该反应通过将由DMF-DMA生成的二甲氨基）甲氧基卡宾的初
• Détermination du site de chélation dans des systèmes cycliques arylhydrazone–imine à 6 atomes. Échanges intra- et intermoleculaires du proton chélaté
  作者：Roger Pichon、Jean-Yves Le Gall、Pierre Courtot

  DOI：10.1139/v82-004

  日期：1982.1.1

  Chelation sites of the proton and structures of chelated six-atom ring systems have been determined for 2-arylhydrazono-3-aryliminopropane-1-ones and 2-arylhydrazono-1,3-bis(arylimino)propanes. Nuclear magnetic resonance spectroscopy allowed determination in these compounds of two types of exchange of the chelated proton. The first type concerns an intramolecular exchange between the two nitrogen atoms

  质子的螯合位点和螯合六原子环系统的结构已确定为 2-arylhydrazono-3-aryliminopropane-1-ones 和 2-arylhydrazono-1,3-bis(arylimino)propanes。核磁共振波谱允许在这些化合物中测定螯合质子的两种类型的交换。第一种类型涉及腙和亚氨基的两个氮原子之间的分子内交换。我们已经表明内部互变异构平衡取决于几个因素（溶剂、温度和固定在偶氮和亚氨基芳环上的取代基）。第二种类型的交换对应于分子间交换，最有可能是溶质-溶质类型，这取决于溶液的温度和浓度。
• 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。