4-acetyl-5,6-diphenyl-3(2H)-pyridazinone | 75643-43-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: 4-acetyl-5,6-diphenyl-3(2H)-pyridazinone
• 英文别名: 1-(3-Hydroxy-5,6-diphenyl-4-pyridazinyl)ethanone；5-acetyl-3,4-diphenyl-1H-pyridazin-6-one
• CAS: 75643-43-5
• 化学式: C₁₈H₁₄N₂O₂
• 分子量: 290.321
• InChiKey: KMNCCCLXSHQXTM-UHFFFAOYSA-N

物化性质

• 熔点：
  231-232 °C
• 密度：
  1.20±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  58.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-acetyl-5,6-diphenyl-3(2H)-pyridazinone 在 劳森试剂 、 一水合肼 作用下， 以 乙醇 、 甲苯 为溶剂， 反应 12.0h， 生成 3-methyl-4,5-diphenyl-1H-pyrazolo[3,4-c]pyridazine
  参考文献：
  名称：

  Ismail, Mohamed Fekry; Derbala, H.A.Y.; Abul-Yazeed, H.S.E., Gazzetta Chimica Italiana, 1997, vol. 127, # 12, p. 787 - 790

  摘要：

  DOI：
• 作为产物：
  描述：

  benzil monohydrazone 、 乙酰乙酸乙酯 在 sodium ethanolate 作用下， 以 乙醇 为溶剂， 反应 3.0h， 生成 4-acetyl-5,6-diphenyl-3(2H)-pyridazinone
  参考文献：
  名称：

  Antihypertensive 5,6-diarylpyridazin-3-ones

  摘要：

  The synthesis of a series of 5,6-diarylpyridazinones is described. Some members of this series display an antihypertensive effect in both the spontaneously hypertensive rat (SHR) model and the deoxycorticosteroid (DOCA) model of hypertension. The most potent compounds in the series have halogen substituents on the 5,6-diphenyl rings, a beta-substituted alkyl group at the 2 position of the ring, and acetyl or cyano substituent at the 4 position.

  DOI：

  10.1021/jm00186a021

文献信息

• Heilmittelchemische Studien in der heterocyclischen Reihe. 5. Mitteilung. Pyridazine II. Eine neue Pyridazinsynthese
  作者：P. Schmidt、J. Druey

  DOI：10.1002/hlca.19540370116

  日期：——

  A new synthesis of 6-pyridazones starting from three single components is described. The starting materials are (1) and α-diketone, α-ketoaldehyde or glyoxal, (2) a carbonic acid having an active methylene group in α-position, and (3) hydrazine or a monosubstituted hydrazine.

  描述了从三个单一组分开始的6-吡啶并酮的新合成。起始原料是（1）和α-二酮，α-酮醛或乙二醛；（2）在α-位具有活性亚甲基的碳酸；和（3）肼或单取代的肼。
• Synthesis of some new hetarylpyranopyridazines, cinnolines, and hetarylpyridazine derivatives
  作者：M. Abdel-Megid、Y. Gabr、M. A. A. Awas、N. M. Abdel-Fatah

  DOI：10.1007/s10593-010-0433-1

  日期：2009.11

  4-Acetyl-5,6-diphenylpyridazin-3(2H)-one was condensed with 6-chloro-3-formylchromone under different reaction conditions to yield the enone or pyranopyridazine. Both compounds were used in the synthesis of some new hetarylpyranopyridazines. Pyranodipyridazine was obtained via a sequence of reactions of 4-acetyl-5,6-diphenylpyridazin-3(2H)-one with diethyl carbonate, acetic anhydride, and 4-bromobenzenediazonium

  在不同反应条件下，将4-乙酰基-5,6-二苯基哒嗪-3（2H）-1与6-氯-3-甲酰基色酮缩合，生成烯酮或吡喃并哒嗪。两种化合物都用于合成一些新的杂芳基吡喃并哒嗪。吡喃二哒嗪是通过4-乙酰基-5,6-二苯基吡啶并嗪-3（2H）-one与碳酸二乙酯，乙酸酐和4-溴苯重氮的反应序列获得的。哒嗪基丁烷-1,3-二酮与浓硫酸的反应 还研究了H2SO4，POCl3，肼，盐酸羟胺，氰基乙酰胺，硫脲和硫代氨基脲。
• Synthesis, spectroscopic, X-ray diffraction, antimicrobial and antitumor studies of Ni(II) and Co(II) complexes derived from 4-acetyl-5,6-diphenyl-3(2H)-pyridazinone and ethylenediamine
  作者：Omima M.I. Adly、Magdy Shebl、Ebtesam M. Abdelrhman、B.A. El-Shetary

  DOI：10.1016/j.molstruc.2020.128607

  日期：2020.11

  means of Coats–Redfern equations. The activation energies were also used to evaluate kinetic and thermodynamic parameter of the metal complexes including Ea, ΔH, ΔS and ΔG. The XRD patterns for the ligand and its metal complexes indicate crystalline nature with nano particle sizes. The biological activity of the chelating agent and its metal complexes was conducted towards S. aureus and B. subtilis as

  摘要 衍生自 4-乙酰基-5,6-二苯基-3(2H)-哒嗪酮和乙二胺的 Schiff 碱配体与 Ni(II) 和 Co(II) 使用不同的金属盐进行反应；NO3-、AcO-、ClO4- 和 Cl- 生成二元金属配合物。混合配体复合物是通过使用额外的配体合成的，包括8-羟基喹啉或甘氨酸作为氮、氧供体；1,10-菲咯啉或2-氨基吡啶作为氮，氮供体。利用元素和热分析、光谱技术（IR、电子和质量）、电导率和磁化率测量来表征配合物的结构。电子光谱和磁矩测量表明所有配合物都是八面体和四面体。此外，热降解的活化能通过 Coats-Redfern 方程计算。活化能还用于评估金属配合物的动力学和热力学参数，包括 Ea、ΔH、ΔS 和 ΔG。配体及其金属配合物的 XRD 图案表明具有纳米颗粒尺寸的结晶性质。螯合剂及其金属配合物的生物活性针对作为革兰氏阳性菌的金黄色葡萄球菌和枯草芽孢杆菌、作为革兰氏阳性菌的鼠伤寒杆菌和大肠杆菌、白色念珠菌（酵母）和
• A New Route for the Synthesis of Substituted Pyridazines
  作者：Mohamed Abdel‐Megid

  DOI：10.1080/00397910701547847

  日期：2007.9.1

  Abstract Condensation of 4‐acetyl‐5,6‐diphenyl‐2,3‐dihydropyridzin‐3‐one (1) with dimethylformamide dimethylacctal (DMFDMA) afforded the enaminone 2. This could be converted into the pyrazolylpyridazine derivative 4 on reaction with hydrazine hydrate and into pyridazinylpyridazinone 7a,b via coupling with aromatic diazonium salts and subsequent treatment with active methylene compounds. The reaction

  摘要 4-乙酰基-5,6-二苯基-2,3-二氢吡啶-3-酮 (1) 与二甲基甲酰胺二甲基乙酸酯 (DMFDMA) 缩合得到烯胺酮 2。与水合肼反应可将其转化为吡唑基哒嗪衍生物 4并通过与芳族重氮盐偶联并随后用活性亚甲基化合物处理形成哒嗪基哒嗪酮7a、b。在三苯基膦存在下，6与乙炔二羧酸二甲酯反应得到哒嗪基哒嗪衍生物8。在乙酸铵存在下，化合物1在乙酸中回流转化为9，在乙酸中回流得到10。
• Green synthesized pyridazinone derivatives as promising biologically active and anticancer drugs
  作者：Amal Selim、fathy yassin、Ahmed Salama

  DOI：10.21608/ejchem.2021.91700.4409

  日期：2021.9.26

  An efficient synthesis of substituted 4-acetyl-5,6-diphenylpyridazin-3(2H)-one derivatives has been achieved using green chemistry tools such as grinding and microwave heating compared to conventional heating. In this work, 4-acetyl-5,6-diphenylpyridazin-3(2H)-one derivative attached to Schiff-bases, chalcones, pyridine, and pyrrole moieties have been prepared with the aim to possess engaging biological and pharmacological activities. The Schiff-base 2 was obtained by reacting 4-acetyl-5, 6-diphenylpyridazin-3(2H)-one 1 with p-amino acetophenone, and the corresponding chalcones 3a-d were obtained by reacting the Schiff-base 2 with the relevant aldehydes. Novel pyridinyl-pyridazinones 5a-h and pyrrole-pyridazinone derivatives 6a-h were synthesized by the reaction of chalcones 3a-d with different acetyls and aldehydes under grinding, microwave irradiations or under reflux conditions. The synthesized compounds were tested for both Gram-positive and Gram-negative antibacterial activity, antifungal, and anticancer activities. These substances were also evaluated using analytical and spectral data, such as 1HNMR and mass spectrum analysis.

  与传统的加热方法相比，使用研磨和微波加热等绿色化学工具，实现了对取代的4-乙酰基-5,6-二苯基哒嗪-3(2H)-酮衍生物的有效合成。在这项工作中，制备了与席夫碱、查尔酮、吡啶和吡咯部分相连的4-乙酰基-5,6-二苯基哒嗪-3(2H)-酮衍生物，目的是使其具有吸引人的生物和药理活性。席夫碱2是通过将4-乙酰基-5,6-二苯基哒嗪-3(2H)-酮1与对氨基苯乙酮反应而获得的，而相应的查尔酮3a-d是通过将席夫碱2与相关醛反应而获得的。通过在研磨、微波辐射或回流条件下将查尔酮3a-d与不同的乙酰基和醛反应，合成了新型吡啶基哒嗪酮5a-h和吡咯基哒嗪酮衍生物6a-h。对合成的化合物进行了革兰氏阳性和阴性抗菌活性、抗真菌和抗癌活性的测试。还利用1HNMR和质谱分析等分析和光谱数据对这些物质进行了评估。