1-(4'-nitrophenyl)-2-(4'-methylphenyl)ethanedione | 35010-13-0

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: 1-(4'-nitrophenyl)-2-(4'-methylphenyl)ethanedione
• 英文别名: 1-(4-nitrophenyl)-2-(p-tolyl)ethane-1,2-dione；1-(4-nitrophenyl)-2-(para-tolyl)ethane-1,2-dione；1-(4-methylphenyl)-2-(4-nitrophenyl)ethanedione；1-(4-Nitrophenyl)-2-p-tolyl-ethane-1,2-dione；1-(4-methylphenyl)-2-(4-nitrophenyl)ethane-1,2-dione
• CAS: 35010-13-0
• 化学式: C₁₅H₁₁NO₄
• 分子量: 269.257
• InChiKey: DRYPSQIFTCBNBV-UHFFFAOYSA-N

物化性质

• 熔点：
  179-180 °C(Solv: chloroform (67-66-3))
• 沸点：
  465.0±38.0 °C(Predicted)
• 密度：
  1.291±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  80
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-(4'-nitrophenyl)-2-(4'-methylphenyl)ethanedione 在 1,3-bis-n-butylimidazolium bromide 作用下， 以 二甲基亚砜 为溶剂， 生成 N-(2-morpholinoethyl)-6-(4-nitrophenyl)-5-(p-tolyl)-1,2,4-triazin-3-amine
  参考文献：
  名称：

  Design, green synthesis and pharmacological evaluation of novel 5,6-diaryl-1,2,4-triazines bearing 3-morpholinoethylamine moiety as potential antithrombotic agents

  摘要：

  The aim of this research work was to investigate a series of novel 5,6-diaryl-1,2,4-triazines (3a-3q) containing 3-morpholinoethylamine side chain, and to address their antiplatelet activity by in vitro, ex vivo and in vivo methods. All compounds were synthesized by environment benign route and their structures were unambiguously confirmed by spectral data. Compounds (3l) and (3m) were confirmed by their single crystal X-ray structures. Out of all the synthesized compounds, 10 were found to be more potent in vitro than aspirin; six of them were found to be prominent in ex vivo assays and one compound (3d) was found to have the most promising antithrombotic profile in vivo. Moreover, compound (3d) demonstrated less ulcerogenicity in rats as compared to aspirin. The selectivity of the most promising compound (3d) for COX-1 and COX-2 enzymes was determined with the help of molecular docking studies and the results were correlated with the biological activity.

  DOI：

  10.3109/14756366.2015.1060480
• 作为产物：
  描述：

  甲苯 在 selenium(IV) oxide 作用下， 以 二甲基亚砜 为溶剂， 反应 0.01h， 生成 1-(4'-nitrophenyl)-2-(4'-methylphenyl)ethanedione
  参考文献：
  名称：

  邻二芳基吡咯基尿素衍生物可通过抑制SOAT酶发挥潜在的降低胆固醇的作用。

  摘要：

  合成了一系列新颖的邻位二芳基唑-脲衍生物，并评估了其抑制SOAT酶的潜力。在所报道的化合物中，化合物（12d）成为最有效的化合物，IC50值为2.43μM。在polaxamer-407诱导的脂蛋白脂肪酶抑制模型中，化合物（12d）降低了体内甘油三酸酯的转化率。化合物（12d）还以30mg / kg的剂量显示出剂量依赖性的血清总胆固醇预防和LDL-C升高的预防。此外，化合物（12d）显示出潜在地剂量依赖性地阻止血清HDL-C水平下降并改善动脉粥样硬化指数。研究了12d对体重，斑块形成和动脉粥样硬化病变发展的影响。化合物（12d）的毒理学研究表明，以2000 mg / kg的剂量，

  DOI：

  10.1016/j.ejmech.2017.02.038

文献信息

• Visible-Light-Induced Photocatalytic Oxidative Decarboxylation of Cinnamic Acids to 1,2-Diketones
  作者：Shiv Chand、Anand Kumar Pandey、Rahul Singh、Krishna Nand Singh

  DOI：10.1021/acs.joc.1c00322

  日期：2021.5.7

  A concerted metallophotoredox catalysis has been realized for the efficient decarboxylative functionalization of α,β-unsaturated carboxylic acids with aryl iodides in the presence of perylene bisimide dye to afford 1,2-diketones.

  已经实现了协同的金属光氧化还原催化，以在of双酰亚胺染料的存在下用芳基碘将α，β-不饱和羧酸有效地脱羧官能化，得到1,2-二酮。
• Rhodium-Catalyzed Enantioselective Addition to Unsymmetrical α-Diketones: Tandem One-Pot Synthesis of Optically Active 3-Tetrasubstituted Isochroman Derivatives
  作者：Ting-Shun Zhu、Jian-Ping Chen、Ming-Hua Xu

  DOI：10.1002/chem.201203701

  日期：2013.1.14

  The domino effect: An efficient and general catalytic one‐pot synthesis of quaternary‐substituted isochroman derivatives has been developed (see scheme). The cascade transformation relies on rhodium‐catalyzed highly regio‐ and enantioselective 1,2‐addition of arylboronic acids to unsymmetrical α‐diketones and intramolecular etherification or esterification, and provides a variety of enantioenriched

  多米诺效应：已经开发出一种高效且通用的单取代季铵盐异色满衍生物的催化一锅合成方法（请参见方案）。级联转化依赖于铑催化的高度芳基和对映选择性的1,2-芳基硼酸加成至不对称的α-二酮和分子内醚化或酯化反应，并在异常温和的条件下提供了多种对映体富集的异色酮。
• Room-Temperature Ionic Liquid–DMSO Promoted and Improved One-Pot Synthesis of 5,6-Diaryl-1,2,4-triazines
  作者：Riyaj S. Tamboli、Rajani Giridhar、Hemant M. Mande、Shailesh R. Shah、Mange Ram Yadav

  DOI：10.1080/00397911.2014.891040

  日期：2014.8.3

  improved and rapid one-pot synthesis of 5,6-diarylsubstituted-1,2,4-triazines in a mixture of room-temperature ionic liquid 1,3-dibutylimidazolium bromide [Bbim]+Br− and dimethylsulfoxide (DMSO) is described without the need for any added catalyst. Different polar aprotic solvents were screened along with ionic liquids and a synergistic effect with DMSO has been found. The predominance of one regioisomer

  摘要 在室温离子液体溴化 1,3-二丁基咪唑鎓 [Bbim]+Br− 和二甲亚砜 (DMSO) 的混合物中改进和快速一锅法合成 5,6-二芳基取代的-1,2,4-三嗪是无需任何添加的催化剂进行描述。与离子液体一起筛选了不同的极性非质子溶剂，并发现了与 DMSO 的协同效应。还研究了在不同反应温度下一种区域异构体优于另一种区域异构体的情况。通过简单的后处理程序实现了在短时间内获得出色分离产量的一锅法。离子液体被有效回收并重复使用3次而没有失去催化作用。所有化合物均通过红外、核磁共振、质谱和元素分析进行​​表征。图形概要
• Synthesis, antileukemic and antiplatelet activities of 2,3-diaryl-6,7-dihydro-5H-1,4-diazepines
  作者：R. Ramajayam、Rajani Giridhar、M.R. Yadav、R. Balaraman、Hakim Djaballah、David Shum、Constantin Radu

  DOI：10.1016/j.ejmech.2007.11.023

  日期：2008.9

  The synthesis, antileukemic and antiplatelet activity evaluation of 2,3-diaryl-6,7-dihydro-5H-1,4-diazepines are described. In general, it was found that compound 17o showed moderate antileukemic activity against MOLT3 human leukemic cancer cell lines. An arachidonic acid induced platelet aggregation effect on washed rat platelets was studied. Compound 17i was found to be the most potent. The antiplatelet

  描述了2,3-二芳基-6,7-二氢-5H-1,4-二氮杂卓的合成，抗白血病和抗血小板活性的评价。通常，发现化合物17o显示出对MOLT3人白血病癌细胞系的中等抗白血病活性。研究了花生四烯酸对洗涤过的大鼠血小板的血小板聚集作用。发现化合物17i是最有效的。抗血小板特性可以通过干扰花生四烯酸途径来介导。
• One-Pot Synthesis of Unsymmetrical Benzils by Oxidative Coupling Using Selenium Dioxide and p-Toluenesulfonic Acid Monohydrate
  作者：Md. Rumum Rohman、Icydora Kharkongor、Mantu Rajbangshi、Hormi Mecadon、Badaker M. Laloo、Priti R. Sahu、Iadeishisha Kharbangar、Bekington Myrboh

  DOI：10.1002/ejoc.201101012

  日期：2012.1

  The oxidative coupling of the α-carbon atom of aromatic ketones with unactivated arenes in the presence of selenium dioxide and p-toluenesulfonic acid monohydrate is described. A number of unsymmetrical benzils have been prepared in good yields (38–75 %) with high regioselectivity. The generality and functional tolerance of this new protocol is demonstrated. The mechanistic pathway for the oxidative

  描述了在二氧化硒和对甲苯磺酸一水合物存在下芳族酮的 α-碳原子与未活化的芳烃的氧化偶联。已经以高产率 (38–75%) 和高区域选择性制备了许多不对称苯偶氮化合物。该新协议的通用性和功能耐受性得到了证明。还描述了氧化偶联反应的机理途径。在 SeO2 和 pTsOH·H2O 促进 C-C 键形成的最小化步骤方面，该反应显示出优势。该方法是有利的，因为可以回收用作溶剂的反应物。